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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 38, 2023 - Issue 1
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Research Paper

Synthesis, in silico modelling, and in vitro biological evaluation of substituted pyrazole derivatives as potential anti-skin cancer, anti-tyrosinase, and antioxidant agents

Samuel T. Boatenga School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Tithi Roya School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Kara Torreyb Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, Bioactive Botanical Research Laboratory, University of Rhode Island, Kingston, RI, USAView further author information
,
Uchechi Owunnac School of Sciences, College of Arts, Education and Sciences, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Sergette Banang-Mbeumia School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USA;d School of Nursing and Allied Health Sciences, Louisiana Delta Community College, Monroe, LA, USAView further author information
,
David Basnetc School of Sciences, College of Arts, Education and Sciences, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Eleonora Nieddae Department of Medicine, Surgery and Pharmacy, University of Sassari, Sassari, ItalyView further author information
,
Alexis D. Alexandera School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Denzel El Hagec School of Sciences, College of Arts, Education and Sciences, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Siriki Atchimnaiduc School of Sciences, College of Arts, Education and Sciences, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Bolni Marius Nagalof Department of Pathology, University of Arkansas for Medical Sciences (UAMS), Little Rock, AR, USA;g The Winthrop P. Rockefeller Cancer Institute, UAMS, Little Rock, AR, USAView further author information
,
Dinesh Aryala School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USA;h Department of Biomedical Affairs and Research, Edward Via College of Osteopathic Medicine, Monroe, LA, USAView further author information
,
Ann Findleyc School of Sciences, College of Arts, Education and Sciences, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Navindra P. Seeramb Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, Bioactive Botanical Research Laboratory, University of Rhode Island, Kingston, RI, USAView further author information
,
Tatiana Efimovai Department of Biomedical Engineering, Northwestern University, Chicago, IL, USAView further author information
,
Mario Sechie Department of Medicine, Surgery and Pharmacy, University of Sassari, Sassari, ItalyView further author information
,
Ronald A. Hilla School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USAView further author information
,
Hang Mab Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, Bioactive Botanical Research Laboratory, University of Rhode Island, Kingston, RI, USAView further author information
,
Jean Christopher Chamcheua School of Basic Pharmaceutical and Toxicological Sciences, College of Pharmacy, University of Louisiana at Monroe, Monroe, LA, USACorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-3927-5664View further author information
ORCID Icon &
Siva Murruc School of Sciences, College of Arts, Education and Sciences, University of Louisiana at Monroe, Monroe, LA, USACorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0002-1956-3079View further author information
ORCID Icon show all
Article: 2205042 | Received 23 Nov 2022, Accepted 16 Apr 2023, Published online: 15 May 2023

References

  • Leiter U, Keim U, Garbe C. Epidemiology of skin cancer: update 2019. Adv Exp Med Biol. 2020;1268:123–139.
  • Wright CY, Millar DA, Wright CY, Du PDJ, Du PDJ, Norval M. The epidemiology of skin cancer and public health strategies for its prevention in Southern Africa. Int J Environ Res Public Health. 2020;17(3):1017.
  • Karimkhani C, Green AC, Nijsten T, Weinstock MA, Dellavalle RP, Naghavi M, Fitzmaurice C. The global burden of melanoma: results from the Global Burden of Disease Study 2015. Br J Dermatol. 2017;177(1):134–140.
  • Yousefi H, Mohammadzadeh S, Irompour A, Shenasifam N, Roshandel E, Jalili A. Overall study on molecular pathways of skin cancer derived from ultraviolet radiation as an environmental threat. Environ Conserv J. 2015;16(SE):547–555.
  • Rivas M, Rojas E, Araya MC, Calaf GM. Ultraviolet light exposure, skin cancer risk and vitamin D production. Oncol Lett. 2015;10(4):2259–2264.
  • Rigby CM, Roy S, Deep G, Guillermo-Lagae R, Jain AK, Dhar D, Orlicky DJ, Agarwal C, Agarwal R. Role of p53 in silibinin-mediated inhibition of ultraviolet B radiation-induced DNA damage, inflammation and skin carcinogenesis. Carcinogenesis. 2017;38(1):40–50.
  • Pavel TI, Chircov C, Rădulescu M, Grumezescu AM. Regenerative wound dressings for skin cancer. Cancers. 2020;12(10):2954.
  • Mulvaney PM, Schmults CD. Molecular prediction of metastasis in cutaneous squamous cell carcinoma. Curr Opin Oncol. 2020;32(2):129–136.
  • Robertson BF, Wokes JET, Siddiqui H. Management of incompletely excised skin tumors: our experience. Dermatol Surg. 2018;44(3):365–369.
  • Adefusika JA, Pimentel JD, Chavan RN, Brewer JD. Primary mucinous carcinoma of the skin: the Mayo Clinic experience over the past 2 decades. Dermatol Surg. 2015;41(2):201–208.
  • Lu Y-g, Wang Y-y, Yang Y-d, Zhang X-c, Gao Y, Yang Y, Zhang J-b, Li G-l. Efficacy of topical ALA-PDT combined with excision in the treatment of skin malignant tumor. Photodiagn Photodyn Ther. 2014;11(2):122–126.
  • Zhi D, Yang T, Zhang T, Yang M, Zhang S, Donnelly RF. Microneedles for gene and drug delivery in skin cancer therapy. J Control Release. 2021;335:158–177.
  • Hwang S-Y, Chae J-I, Kwak A-W, Lee M-H, Shim J-H. Alternative options for skin cancer therapy via regulation of AKT and related signaling pathways. Int J Mol Sci. 2020;21(18):6869.
  • Jain R, Sarode I, Singhvi G, Dubey SK. Nanocarrier based topical drug delivery – a promising strategy for treatment of skin cancer. Curr Pharm Des. 2020;26(36):4615–4623.
  • Ascierto PA, Garbe C. Updates and new perspectives in nonmelanoma skin cancer therapy: highlights from 'Immunotherapy Bridge’. Immunotherapy. 2020;12(3):167–174.
  • Solomon EI, Sundaram UM, Machonkin TE. Multicopper oxidases and oxygenases. Chem Rev. 1996;96(7):2563–2606.
  • Saeedi M, Khezri K, Seyed Zakaryaei A, Mohammadamini H. A comprehensive review of the therapeutic potential of α-arbutin. Phytother Res. 2021;35(8):4136–4154.
  • Li H, DaSilva NA, Liu W, Xu J, Dombi GW, Dain JA, Li D, Chamcheu JC, Seeram NP, Ma H. Thymocid(®), a standardized black cumin (Nigella sativa) seed extract, modulates collagen cross-linking, collagenase and elastase activities, and melanogenesis in murine B16F10 melanoma cells. Nutrients. 2020;12(7):2146.
  • Pillaiyar T, Namasivayam V, Manickam M, Jung SH. Inhibitors of melanogenesis: an updated review. J Med Chem. 2018;61(17):7395–7418.
  • Li Y, Huang J, Lu J, Ding Y, Jiang L, Hu S, Chen J, Zeng Q. The role and mechanism of Asian medicinal plants in treating skin pigmentary disorders. J Ethnopharmacol. 2019;245:112173.
  • Liu-Smith F, Meyskens FL. Molecular mechanisms of flavonoids in melanin synthesis and the potential for the prevention and treatment of melanoma. Mol Nutr Food Res. 2016;60(6):1264–1274.
  • Nirmal NP, Benjakul S, Ahmad M, Arfat YA, Panichayupakaranant P. Undesirable enzymatic browning in crustaceans: causative effects and its inhibition by phenolic compounds. Crit Rev Food Sci Nutr. 2015;55(14):1992–2003.
  • Sánchez-Ferrer A, Rodríguez-López JN, García-Cánovas F, García-Carmona F. Tyrosinase: a comprehensive review of its mechanism. Biochim Biophys Acta. 1995;1247(1):1–11.
  • Min K, Park GW, Yoo YJ, Lee JS. A perspective on the biotechnological applications of the versatile tyrosinase. Bioresour Technol. 2019;289:121730.
  • Olivares C, Solano F. New insights into the active site structure and catalytic mechanism of tyrosinase and its related proteins. Pigment Cell Melanoma Res. 2009;22(6):750–760.
  • Ioniţă E, Aprodu I, Stănciuc N, Râpeanu G, Bahrim G. Advances in structure–function relationships of tyrosinase from Agaricus bisporus – investigation on heat-induced conformational changes. Food Chem. 2014;156:129–136.
  • Chang TS. An updated review of tyrosinase inhibitors. Int J Mol Sci. 2009;10(6):2440–2475.
  • Pillaiyar T, Manickam M, Jung SH. Downregulation of melanogenesis: drug discovery and therapeutic options. Drug Discov Today. 2017;22(2):282–298.
  • Brenner M, Hearing VJ. The protective role of melanin against UV damage in human skin. Photochem Photobiol. 2008;84(3):539–549.
  • Ray K, Chaki M, Sengupta M. Tyrosinase and ocular diseases: some novel thoughts on the molecular basis of oculocutaneous albinism type 1. Prog Retin Eye Res. 2007;26(4):323–358.
  • Hearing VJ, Tsukamoto K. Enzymatic control of pigmentation in mammals. FASEB J. 1991;5(14):2902–2909.
  • Costin GE, Hearing VJ. Human skin pigmentation: melanocytes modulate skin color in response to stress. FASEB J. 2007;21(4):976–994.
  • Videira IF, Moura DF, Magina S. Mechanisms regulating melanogenesis. An Bras Dermatol. 2013;88(1):76–83.
  • Ghanem G, Fabrice J. Tyrosinase related protein 1 (TYRP1/gp75) in human cutaneous melanoma. Mol Oncol. 2011;5(2):150–155.
  • Gradilone A, Cigna E, Aglianò AM, Frati L. Tyrosinase expression as a molecular marker for investigating the presence of circulating tumor cells in melanoma patients. Curr Cancer Drug Targets. 2010;10(5):529–538.
  • Jawaid S, Khan TH, Osborn HM, Williams NA. Tyrosinase activated melanoma prodrugs. Anticancer Agents Med Chem. 2009;9(7):717–727.
  • Lee SY, Baek N, Nam TG. Natural, semisynthetic and synthetic tyrosinase inhibitors. J Enzyme Inhib Med Chem. 2016;31(1):1–13.
  • Pillaiyar T, Manickam M, Namasivayam V. Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors. J Enzyme Inhib Med Chem. 2017;32(1):403–425.
  • Ando H, Ichihashi M, Hearing VJ. Role of the ubiquitin proteasome system in regulating skin pigmentation. Int J Mol Sci. 2009;10(10):4428–4434.
  • Zolghadri S, Bahrami A, Hassan Khan MT, Munoz-Munoz J, Garcia-Molina F, Garcia-Canovas F, Saboury AA. A comprehensive review on tyrosinase inhibitors. J Enzyme Inhib Med Chem. 2019;34(1):279–309.
  • Zhao Y, Hu JJ, Bai XL, Liu HP, Qi XW, Liao X. Fast screening of tyrosinase inhibitors from traditional Chinese medicinal plants by ligand fishing in combination with in situ fluorescent assay. Anal Bioanal Chem. 2022;414(6):2265–2273.
  • Chidambaram S, Ali D, Alarifi S, Gurusamy R, Radhakrishnan S, Akbar I. Tyrosinase-mediated synthesis of larvicidal active 1,5-diphenyl pent-4-en-1-one derivatives against Culex quinquefasciatus and investigation of their ichthyotoxicity. Sci Rep. 2021;11(1):20730.
  • Blaschek L, Pesquet E. Phenoloxidases in plants—how structural diversity enables functional specificity. Front Plant Sci. 2021;12:754601.
  • Pacelli C, Cassaro A, Maturilli A, Timperio AM, Gevi F, Cavalazzi B, Stefan M, Ghica D, Onofri S. Multidisciplinary characterization of melanin pigments from the black fungus Cryomyces antarcticus. Appl Microbiol Biotechnol. 2020;104(14):6385–6395.
  • Dolinska MB, Wingfield PT, Sergeev YV. Purification of recombinant human tyrosinase from insect larvae infected with the baculovirus vector. Curr Protoc Protein Sci. 2017;89:6.15.1–6.15.12.
  • Cordes P, Sun W, Wolber R, Kolbe L, Klebe G, Röhm KH. Expression in non-melanogenic systems and purification of soluble variants of human tyrosinase. Biol Chem. 2013;394(5):685–693.
  • Matoba Y, Kumagai T, Yamamoto A, Yoshitsu H, Sugiyama M. Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J Biol Chem. 2006;281(13):8981–8990.
  • Kim YJ, Uyama H. Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci. 2005;62(15):1707–1723.
  • Parvez S, Kang M, Chung HS, Bae H. Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother Res. 2007;21(9):805–816.
  • Goenka S, Johnson F, Simon SR. Novel chemically modified curcumin (CMC) derivatives inhibit tyrosinase activity and melanin synthesis in B16F10 mouse melanoma cells. Biomolecules. 2021;11(5):674.
  • Sendovski M, Kanteev M, Ben-Yosef VS, Adir N, Fishman A. First structures of an active bacterial tyrosinase reveal copper plasticity. J Mol Biol. 2011;405(1):227–237.
  • Bijelic A, Pretzler M, Molitor C, Zekiri F, Rompel A. The structure of a plant tyrosinase from walnut leaves reveals the importance of "substrate-guiding residues" for enzymatic specificity. Angew Chem Int Ed Engl. 2015;54(49):14677–14680.
  • Qu Y, Zhan Q, Du S, Ding Y, Fang B, Du W, Wu Q, Yu H, Li L, Huang W. Catalysis-based specific detection and inhibition of tyrosinase and their application. J Pharm Anal. 2020;10(5):414–425.
  • McLarin MA, Leung IKH. Substrate specificity of polyphenol oxidase. Crit Rev Biochem Mol Biol. 2020;55(3):274–308.
  • Fenoll LG, Peñalver MJ, Rodríguez-López JN, Varón R, García-Cánovas F, Tudela J. Tyrosinase kinetics: discrimination between two models to explain the oxidation mechanism of monophenol and diphenol substrates. Int J Biochem Cell Biol. 2004;36(2):235–246.
  • Ghose AK, Viswanadhan VN, Wendoloski JJ. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem. 1999;1(1):55–68.
  • Bocci G, Carosati E, Vayer P, Arrault A, Lozano S, Cruciani G. ADME-Space: a new tool for medicinal chemists to explore ADME properties. Sci Rep. 2017;7(1):6359.
  • Eid AM, Hawash M, Amer J, Jarrar A, Qadri S, Alnimer I, Sharaf A, Zalmoot R, Hammoudie O, Hameedi S, et al. Synthesis and biological evaluation of novel isoxazole-amide analogues as anticancer and antioxidant agents. Biomed Res Int. 2021;2021:6633297.
  • Gabrič A, Hodnik Ž, Pajk S. Oxidation of drugs during drug product development: problems and solutions. Pharmaceutics. 2022;14(2):325.
  • Ramadan M, Aly AA, El-Haleem LEA, Alshammari MB, Bräse S. Substituted pyrazoles and their heteroannulated analogs-recent syntheses and biological activities. Molecules. 2021;26(16):4995.
  • Farghaly TA, Dawood KM. Inhibitory activities of pyrazolo-oxazine heterocyclic derivatives. Mini Rev Med Chem. 2021;22(9):1256–1267.
  • Mantzanidou M, Pontiki E, Hadjipavlou-Litina D. Pyrazoles and pyrazolines as anti-inflammatory agents. Molecules. 2021;26(11):3439.
  • Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules. 2020;25(8):1909.
  • Dhameliya TM, Chudasma SJ, Patel TM, Dave BP. A review on synthetic account of 1,2,4-oxadiazoles as anti-infective agents. Mol Divers. 2022;26(5):2967–2980.
  • Costa RF, Turones LC, Cavalcante KVN, Rosa Júnior IA, Xavier CH, Rosseto LP, Napolitano HB, Castro PFdS, Neto MLF, Galvão GM, et al. Heterocyclic compounds: pharmacology of pyrazole analogs from rational structural considerations. Front Pharmacol. 2021;12:666725.
  • Sharma R, Chawla PA, Chawla V, Verma R, Nawal N, Gupta V. A therapeutic journey of 5-pyrazolones as a versatile scaffold: a review. Mini Rev Med Chem. 2021;21(13):1770–1795.
  • Karrouchi K, Radi S, Ramli Y, Taoufik J, Mabkhot Y, Al-Aizari F, Ansar M. Synthesis and pharmacological activities of pyrazole derivatives: a review. Molecules. 2018;23(1):134.
  • Bennani FE, Doudach L, Cherrah Y, Ramli Y, Karrouchi K, Ansar M, Faouzi MEA. Overview of recent developments of pyrazole derivatives as an anticancer agent in different cell line. Bioorg Chem. 2020;97:103470.
  • Mor S, Khatri M, Punia R, Sindhu S. Recent progress in anticancer agents incorporating pyrazole scaffold. Mini Rev Med Chem. 2022;22(1):115–163.
  • Hawash MM, Kahraman DC, Eren F, Cetin Atalay R, Baytas SN. Synthesis and biological evaluation of novel pyrazolic chalcone derivatives as novel hepatocellular carcinoma therapeutics. Eur J Med Chem. 2017;129:12–26.
  • Jing L, Wang L, Zhao Y, Tan R, Xing X, Liu T, Huang W, Luo Y, Li Z. Synthesis, crystal structure and evaluation of cancer inhibitory activity of 4-[indol-3-yl-methylene]-1H-pyrazol-5(4H)-one derivatives. J Chem Res. 2012;36(12):691–696.
  • Huang S, Lin R, Yu Y, Lu Y, Connolly PJ, Chiu G, Li S, Emanuel SL, Middleton SA. Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor. Bioorg Med Chem Lett. 2007;17(5):1243–1245.
  • Baytas SN, Inceler N, Yılmaz A. Synthesis, cytotoxicity, and molecular properties prediction of novel 1,3-diarylpyrazole derivatives. Med Chem Res. 2013;22(10):4893–4908.
  • Doan NQH, Nguyen NTK, Duong VB, Nguyen HTT, Vong LB, Duong DN, Nguyen N-TT, Nguyen TLT, Do TTH, Truong TN. Synthesis, biological evaluation, and molecular modeling studies of 1-aryl-1H-pyrazole-fused curcumin analogues as anticancer agents. ACS Omega. 2022;7(38):33963–33984.
  • Hawash M. Recent advances of tubulin inhibitors targeting the colchicine binding site for cancer therapy. Biomolecules. 2022;12(12):1843.
  • Taher AT, Mostafa Sarg MT, El-Sayed Ali NR, Hilmy Elnagdi N. Design, synthesis, modeling studies and biological screening of novel pyrazole derivatives as potential analgesic and anti-inflammatory agents. Bioorg Chem. 2019;89:103023.
  • Ran F, Liu Y, Zhang D, Liu M, Zhao G. Discovery of novel pyrazole derivatives as potential anticancer agents in MCL. Bioorg Med Chem Lett. 2019;29(9):1060–1064.
  • Faisal M, Saeed A, Hussain S, Dar PM, Larik FA. Recent developments in synthetic chemistry and biological activities of pyrazole derivatives. J Chem Sci. 2019;131(8):70.
  • He B, Lu C, Zheng G, He X, Wang M, Chen G, Zhang G, Lu A. Combination therapeutics in complex diseases. J Cell Mol Med. 2016;20(12):2231–2240.
  • van Vlijmen H, Ortholand JY, Li VM, de Vlieger JSB. The European lead factory: an updated HTS compound library for innovative drug discovery. Drug Discov Today. 2021;26(10):2406–2413.
  • Lipinski C, Hopkins A. Navigating chemical space for biology and medicine. Nature. 2004;432(7019):855–861.
  • Tran PHL, Duan W, Lee B-J, Tran TTD. Nanogels for skin cancer therapy via transdermal delivery: current designs. Curr Drug Metab. 2019;20(7):575–582.
  • Ma X, Qu Q, Zhao Y. Targeted delivery of 5-aminolevulinic acid by multifunctional hollow mesoporous silica nanoparticles for photodynamic skin cancer therapy. ACS Appl Mater Interfaces. 2015;7(20):10671–10676.
  • Feoktistova M, Panayotova-Dimitrova D. Overcoming cell death resistance in skin cancer therapy: novel translational perspectives. Exp Dermatol. 2017;26(10):854–857.
  • Dong L, Li Y, Li Z, Xu N, Liu P, Du H, Zhang Y, Huang Y, Zhu J, Ren G, et al. Au nanocage-strengthened dissolving microneedles for chemo-photothermal combined therapy of superficial skin tumors. ACS Appl Mater Interfaces. 2018;10(11):9247–9256.
  • Liu J, Sun L, Li L, Zhang R, Xu ZP. Synergistic cancer photochemotherapy via layered double hydroxide-based trimodal nanomedicine at very low therapeutic doses. ACS Appl Mater Interfaces. 2021;13(6):7115–7126.
  • Silk T, Wu J. Cutaneous toxicities of targeted therapies in the treatment of hepatocellular carcinoma. Hepatoma Res. 2020;6(Spec. Iss.):1–16.
  • Hawash M, Jaradat N, Eid AM, Abubaker A, Mufleh O, Al-Hroub Q, Sobuh S. Synthesis of novel isoxazole-carboxamide derivatives as promising agents for melanoma and targeted nano-emulgel conjugate for improved cellular permeability. BMC Chem. 2022;16(1):47.
  • Dahal A, Lo M, Singh S, Vo H, ElHage D, Jois SD, Murru S. 1,3-Diarylpyrazolones as potential anticancer agents for non-small cell lung cancer: synthesis and antiproliferative activity evaluation. Chem Biol Drug Des. 2022;99(4):620–633.
  • Mohamed Ahmed MS, Kobayashi K, Mori A. One-pot construction of pyrazoles and isoxazoles with palladium-catalyzed four-component coupling. Org Lett. 2005;7(20):4487–4489.
  • Dissanayake AA, Odom AL. Single-step synthesis of pyrazoles using titanium catalysis. Chem Commun. 2012;48(3):440–442.
  • Ding Z, Tan Q, Gao M, Xu B. Copper-catalyzed aerobic cascade cycloamination and acyloxylation: a direct approach to 4-acyloxy-1H-pyrazoles. Org Biomol Chem. 2015;13(16):4642–4646.
  • Harigae R, Moriyama K, Togo H. Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine. J Org Chem. 2014;79(5):2049–2058.
  • Heller ST, Natarajan SR. 1,3-Diketones from acid chlorides and ketones: a rapid and general one-pot synthesis of pyrazoles. Org Lett. 2006;8(13):2675–2678.
  • Kirkham JD, Edeson SJ, Stokes S, Harrity JP. Synthesis of ynone trifluoroborates toward functionalized pyrazoles. Org Lett. 2012;14(20):5354–5357.
  • Zhang G, Ni H, Chen W, Shao J, Liu H, Chen B, Yu Y. One-pot three-component approach to the synthesis of polyfunctional pyrazoles. Org Lett. 2013;15(23):5967–5969.
  • Deng X, Mani NS. Reaction of N-monosubstituted hydrazones with nitroolefins: a novel regioselective pyrazole synthesis. Org Lett. 2006;8(16):3505–3508.
  • Peruncheralathan S, Yadav AK, Ila H, Junjappa H. Highly regioselective synthesis of 1-aryl-3 (or 5)-alkyl/aryl-5 (or 3)-(N-cycloamino)pyrazoles. J Org Chem. 2005;70(23):9644–9647.
  • Persson T, Nielsen J. Synthesis of N-methoxy-N-methyl-beta-enaminoketoesters: new synthetic precursors for the regioselective synthesis of heterocyclic compounds. Org Lett. 2006;8(15):3219–3222.
  • Peruncheralathan S, Khan TA, Ila H, Junjappa H. Regioselective synthesis of 1-aryl-3,4-substituted/annulated-5-(methylthio)pyrazoles and 1-aryl-3-(methylthio)-4,5-substituted/annulated pyrazoles. J Org Chem. 2005;70(24):10030–10035.
  • Bernhammer JC, Huynh HV. Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles. Dalton Trans. 2012;41(28):8600–8608.
  • Pünner F, Schieven J, Hilt G. Synthesis of fluorenone and anthraquinone derivatives from aryl- and aroyl-substituted propiolates. Org Lett. 2013;15(18):4888–4891.
  • Nakamichi N, Kawashita Y, Hayashi M. Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid. Org Lett. 2002;4(22):3955–3957.
  • Rzepecki LM, Waite JH. A chromogenic assay for catecholoxidases based on the addition of l-proline to quinones. Anal Biochem. 1989;179(2):375–381.
  • Wang Y, Hao M-M, Sun Y, Wang L-F, Wang H, Zhang Y-J, Li H-Y, Zhuang P-W, Yang Z. Synergistic promotion on tyrosinase inhibition by antioxidants. Molecules. 2018;23(1):106.
  • Ashraf Z, Rafiq M, Nadeem H, Hassan M, Afzal S, Waseem M, Afzal K, Latip J. Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies. PLOS One. 2017;12(5):e0178069.
  • Pintus F, Matos MJ, Vilar S, Hripcsak G, Varela C, Uriarte E, Santana L, Borges F, Medda R, Di Petrillo A, et al. New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins: anti-melanogenesis and antioxidant activities, and computational molecular modeling studies. Bioorg Med Chem. 2017;25(5):1687–1695.
  • Chamcheu JC, Esnault S, Adhami VM, Noll AL, Banang-Mbeumi S, Roy T, Singh SS, Huang S, Kousoulas KG, Mukhtar H, et al. Fisetin, a 3,7,3′,4′-tetrahydroxyflavone Inhibits the PI3K/Akt/mTOR and MAPK pathways and ameliorates psoriasis pathology in 2D and 3D organotypic human inflammatory skin models. Cells. 2019;8(9):1089.
  • Roy T, Boateng ST, Banang-Mbeumi S, Singh PK, Basnet P, Chamcheu R-CN, Ladu F, Chauvin I, Spiegelman VS, Hill RA, et al. Synthesis, inverse docking-assisted identification and in vitro biological characterization of flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers. Bioorg Chem. 2021;107:104595.
  • Liu H, Li X, Ji M, Wang N, Xu Y, Kong Y, Gou J, Yin T, He H, Zhang Y, et al. Two-step fabricating micelle-like nanoparticles of cisplatin with the 'real’ long circulation and high bioavailability for cancer therapy. Colloids Surf B Biointerfaces. 2022;210:112225.
  • de la Cour CD, von Buchwald C, Dehlendorff C, Garset-Zamani M, Grønhøj C, Carlander A-LF, Friis S, Kjaer SK. Low-dose aspirin use and mortality risk in patients with head and neck cancer: a nationwide cohort study of 10 770 patients. Int J Cancer. 2022;150(6):969–975.
  • Liebman TN, Stein JA, Polsky D. Cyclo-oxygenase-2 inhibitors for chemoprevention of nonmelanoma skin cancer: is there a role for these agents? J Am Acad Dermatol. 2013;68(1):173–176.
  • Elmets CA, Viner JL, Pentland AP, Cantrell W, Lin H-Y, Bailey H, Kang S, Linden KG, Heffernan M, Duvic M, et al. Chemoprevention of nonmelanoma skin cancer with celecoxib: a randomized, double-blind, placebo-controlled trial. J Natl Cancer Inst. 2010;102(24):1835–1844.
  • Sultania M, Imaduddin M, Deo SSV, Kar M, Muduly DK, Kumar S, Sharma A, Mishra A, Majumdar SKD, Adhya AK, et al. Role of metronomic therapy for advanced oral cancers and predictors of response: multi-institutional feasibility study. Head Neck. 2022;44(1):104–112.
  • Li Y, Zhou M, Hu Q, Bai X-C, Huang W, Scheres SHW, Shi Y. Mechanistic insights into caspase-9 activation by the structure of the apoptosome holoenzyme. Proc Natl Acad Sci U S A. 2017;114(7):1542–1547.
  • Brzozowska B, Gałecki M, Tartas A, Ginter J, Kaźmierczak U, Lundholm L. Freeware tool for analysing numbers and sizes of cell colonies. Radiat Environ Biophys. 2019;58(1):109–117.
  • Vickers CJ, Gonzalez-Paez GE, Wolan DW. Selective detection and inhibition of active caspase-3 in cells with optimized peptides. J Am Chem Soc. 2013;135(34):12869–12876.
  • Liu D, Tian Z, Yan Z, Wu L, Ma Y, Wang Q, Liu W, Zhou H, Yang C. Design, synthesis and evaluation of 1,2-benzisothiazol-3-one derivatives as potent caspase-3 inhibitors. Bioorg Med Chem. 2013;21(11):2960–2967.
  • Hawash M, Jaradat N, Abualhasan M, Thaher M, Sawalhi R, Younes N, Shanaa A, Nuseirat M, Mousa A. In vitro and in vivo assessment of the antioxidant potential of isoxazole derivatives. Sci Rep. 2022;12(1):18223.
  • Kumara K, Prabhudeva MG, Vagish CB, Vivek HK, Lokanatha Rai KM, Lokanath NK, Ajay Kumar K. Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles. Heliyon. 2021;7(7):e07592.
  • Ali SA, Awad SM, Said AM, Mahgoub S, Taha H, Ahmed NM. Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-lipoxygenase inhibitors. J Enzyme Inhib Med Chem. 2020;35(1):847–863.
  • Cereto-Massagué A, Ojeda MJ, Valls C, Mulero M, Pujadas G, Garcia-Vallve S. Tools for in silico target fishing. Methods. 2015;71:98–103.
  • Daina A, Michielin O, Zoete V. SwissTargetPrediction: updated data and new features for efficient prediction of protein targets of small molecules. Nucleic Acids Res. 2019;47(W1):W357–W364.
  • Armstrong MS, Finn PW, Morris GM, Richards WG. Improving the accuracy of ultrafast ligand-based screening: incorporating lipophilicity into ElectroShape as an extra dimension. J Comput Aided Mol Des. 2011;25(8):785–790.
  • Armstrong MS, Morris GM, Finn PW, Sharma R, Moretti L, Cooper RI, Richards WG. ElectroShape: fast molecular similarity calculations incorporating shape, chirality and electrostatics. J Comput Aided Mol Des. 2010;24(9):789–801.
  • Johnson M, Lajiness M, Maggiore G. Molecular similarity: a basis for designing drug screening programs. Prog Clin Biol Res. 1989;291:167–171.
  • Qin F, Wang Y, Jiang X, Wang Y, Zhang N, Wen X, Wang L, Jiang Q, He G. Design, synthesis and molecular mechanisms of novel dual inhibitors of heat shock protein 90/phosphoinositide 3-kinase alpha (Hsp90/PI3Kα) against cutaneous melanoma. J Enzyme Inhib Med Chem. 2019;34(1):909–926.
  • Egger ME, Huang JS, Yin W, McMasters KM, McNally LR. Inhibition of autophagy with chloroquine is effective in melanoma. J Surg Res. 2013;184(1):274–281.
  • Mielczarek-Lewandowska A, Hartman ML, Czyz M. Inhibitors of HSP90 in melanoma. Apoptosis. 2020;25(1–2):12–28.
  • Zhao Q, Zhu HP, Xie X, Mao Q, Liu YQ, He XH, Peng C, Jiang Q-L, Huang W. Novel HSP90-PI3K dual inhibitor suppresses melanoma cell proliferation by interfering with HSP90-EGFR interaction and downstream signaling pathways. Int J Mol Sci. 2020;21(5):1845.
  • Xiang X, Tu C, Li Q, Wang W, Huang X, Zhao Z, Xiong H, Mei Z. Oxymatrine ameliorates imiquimod-induced psoriasis pruritus and inflammation through inhibiting heat shock protein 90 and heat shock protein 60 expression in keratinocytes. Toxicol Appl Pharmacol. 2020;405:115209.
  • Dickel H, Gambichler T, Kamphowe J, Altmeyer P, Skrygan M. Standardized tape stripping prior to patch testing induces upregulation of Hsp90, Hsp70, IL-33, TNF-α and IL-8/CXCL8 mRNA: new insights into the involvement of 'alarmins’. Contact Dermatitis. 2010;63(4):215–222.
  • Zhang Y, Bai X, Wang Y, Li N, Li X, Han F, Su L, Hu D. Role for heat shock protein 90α in the proliferation and migration of HaCaT cells and in the deep second-degree burn wound healing in mice. PLOS One. 2014;9(8):e103723.
  • Tukaj S, Kleszczyński K, Vafia K, Groth S, Meyersburg D, Trzonkowski P, Ludwig RJ, Zillikens D, Schmidt E, Fischer TW, et al. Aberrant expression and secretion of heat shock protein 90 in patients with bullous pemphigoid. PLOS One. 2013;8(7):e70496.
  • Cengiz FP, Beyaztas S, Gokce B, Arslan O, Guler OO. Catalase, carbonic anhydrase and xanthine oxidase activities in patients with mycosis fungoides. J Enzyme Inhib Med Chem. 2015;30(2):212–215.
  • Noda Y, Oosumi H, Morishima T, Tsujimura T, Mori M. Immunohistochemical study of carbonic anhydrase in mixed tumours and adenomas of sweat and sebaceous glands. J Cutan Pathol. 1987;14(5):285–290.
  • Noda Y, Takai Y, Iwai Y, Meenaghan MA, Mori M. Immunohistochemical study of carbonic anhydrase in mixed tumours from major salivary glands and skin. Virchows Arch A Pathol Anat Histopathol. 1986;408(5):449–459.
  • Kamsteeg M, Jansen PAM, van Vlijmen-Willems IMJJ, van Erp PEJ, Rodijk-Olthuis D, van der Valk PG, Feuth T, Zeeuwen PLJM, Schalkwijk J. Molecular diagnostics of psoriasis, atopic dermatitis, allergic contact dermatitis and irritant contact dermatitis. Br J Dermatol. 2010;162(3):568–578.
  • Suri BK, Verma NK, Schmidtchen A. Toll-like receptor 3 agonist, polyinosinic–polycytidylic acid, upregulates carbonic anhydrase II in human keratinocytes. Acta Derm Venereol. 2018;98(8):762–765.
  • Carfagna MA, Young KM, Susick RL. Sex differences in rat hepatic cytolethality of the protein kinase C inhibitor safingol: role of biotransformation. Toxicol Appl Pharmacol. 1996;137(2):173–181.
  • Wang J, Wang YM, Ahn HY. Biological products for the treatment of psoriasis: therapeutic targets, pharmacodynamics and disease—drug-drug interaction implications. AAPS J. 2014;16(5):938–947.
  • Kyoreva M, Li Y, Hoosenally M, Hardman-Smart J, Morrison K, Tosi I, Tolaini M, Barinaga G, Stockinger B, Mrowietz U, et al. CYP1A1 enzymatic activity influences skin inflammation via regulation of the AHR pathway. J Invest Dermatol. 2021;141(6):1553–1563.e3.
  • Pavez Loriè E, Cools M, Borgers M, Wouters L, Shroot B, Hagforsen E, Törmä H, Vahlquist A. Topical treatment with CYP26 inhibitor talarozole (R115866) dose dependently alters the expression of retinoid-regulated genes in normal human epidermis. Br J Dermatol. 2009;160(1):26–36.
  • Hawerkamp HC, Kislat A, Gerber PA, Pollet M, Rolfes KM, Soshilov AA, Denison MS, Momin AA, Arold ST, Datsi A, et al. Vemurafenib acts as an aryl hydrocarbon receptor antagonist: implications for inflammatory cutaneous adverse events. Allergy. 2019;74(12):2437–2448.
  • Heo M-J, Lee C, Choi SY, Choi YM, An I-S, Bae S, An S, Jung JH. Nintedanib ameliorates animal model of dermatitis. Sci Rep. 2020;10(1):4493.
  • Grun D, Adhikary G, Eckert RL. VEGF-A acts via neuropilin-1 to enhance epidermal cancer stem cell survival and formation of aggressive and highly vascularized tumors. Oncogene. 2016;35(33):4379–4387.
  • de Almeida CM, de Jesus SF, Poswar FdO, Gomes ESB, Fraga CAdC, Farias LC, Santos SHS, Feltenberger JD, de Paula AMB, Guimarães ALS, et al. Increasing demonstration of angiogenic markers in skin neoplastic lesions. Pathol Res Pract. 2016;212(2):101–105.
  • Decoster L, Broek IV, Neyns B, Majois F, Baurain JF, Rottey S, Rorive A, Anckaert E, De Mey J, De Brakeleer S, et al. Biomarker analysis in a phase II study of sunitinib in patients with advanced melanoma. Anticancer Res. 2015;35(12):6893–6899.
  • Mahalingam D, Malik L, Beeram M, Rodon J, Sankhala K, Mita A, Benjamin D, Ketchum N, Michalek J, Tolcher A, et al. Phase II study evaluating the efficacy, safety, and pharmacodynamic correlative study of dual antiangiogenic inhibition using bevacizumab in combination with sorafenib in patients with advanced malignant melanoma. Cancer Chemother Pharmacol. 2014;74(1):77–84.
  • Wen S-Y, Cheng S-Y, Ng S-C, Aneja R, Chen C-J, Huang C-Y, Kuo W-W. Roles of p38α and p38β mitogen-activated protein kinase isoforms in human malignant melanoma A375 cells. Int J Mol Med. 2019;44(6):2123–2132.
  • Choo MK, Kraft S, Missero C, Park JM. The protein kinase p38α destabilizes p63 to limit epidermal stem cell frequency and tumorigenic potential. Sci Signal. 2018;11(551):eaau0727.
  • Liu K, Yu D, Cho Y-Y, Bode AM, Ma W, Yao K, Li S, Li J, Bowden GT, Dong Z, et al. Sunlight UV-induced skin cancer relies upon activation of the p38α signaling pathway. Cancer Res. 2013;73(7):2181–2188.
  • Zheng T, Zhao W, Li H, Xiao S, Hu R, Han M, Liu H, Liu Y, Otsu K, Liu X, et al. p38α signaling in Langerhans cells promotes the development of IL-17-producing T cells and psoriasiform skin inflammation. Sci Signal. 2018;11(521):eaao1685.
  • Liu Q, Zhang S, Chen G, Zhou H. E3 ubiquitin ligase Nedd4 inhibits AP-1 activity and TNF-α production through targeting p38α for polyubiquitination and subsequent degradation. Sci Rep. 2017;7(1):4521.
  • Ondet T, Muscatelli-Groux B, Coulouarn C, Robert S, Gicquel T, Bodin A, Lagente V, Grimaud J-A. The release of pro-inflammatory cytokines is mediated via mitogen-activated protein kinases rather than by the inflammasome signalling pathway in keratinocytes. Clin Exp Pharmacol Physiol. 2017;44(7):827–838.
  • Lilleholt LL, Johansen C, Arthur JS, Funding A, Bibby BM, Kragballe K, Iversen L. Role of p38 mitogen-activated protein kinase isoforms in murine skin inflammation induced by 12-O-tetradecanoylphorbol 13-acetate. Acta Derm Venereol. 2011;91(3):271–278.
  • Theivanthiran B, Kathania M, Zeng M, Anguiano E, Basrur V, Vandergriff T, Pascual V, Wei W-Z, Massoumi R, Venuprasad K, et al. The E3 ubiquitin ligase Itch inhibits p38α signaling and skin inflammation through the ubiquitylation of Tab1. Sci Signal. 2015;8(365):ra22.
  • Xu Y, Chen S, Zhang L, Chen G, Chen J. The anti-inflammatory and anti-pruritus mechanisms of Huanglian Jiedu decoction in the treatment of atopic dermatitis. Front Pharmacol. 2021;12:735295.
  • Martins C, Migayron L, Drullion C, Jacquemin C, Lucchese F, Rambert J, Merhi R, Michon P, Taieb A, Rezvani H-R, et al. Vitiligo skin T cells are prone to produce type 1 and type 2 cytokines to induce melanocyte dysfunction and epidermal inflammatory response through Jak signaling. J Invest Dermatol. 2021;142(4):1194–1205.e7.
  • Nakashima C, Yanagihara S, Otsuka A. Innovation in the treatment of atopic dermatitis: emerging topical and oral Janus kinase inhibitors. Allergol Int. 2022;71(1):40–46.
  • Deeks ED, Duggan S. Abrocitinib: first approval. Drugs. 2021;81(18):2149–2157.
  • Cartron AM, Nguyen TH, Roh YS, Kwatra MM, Kwatra SG. Janus kinase inhibitors for atopic dermatitis: a promising treatment modality. Clin Exp Dermatol. 2021;46(5):820–824.
  • Yang HY, Steenhuis P, Glucksman AM, Gurenko Z, La TD, Isseroff RR. Alpha and beta adrenergic receptors modulate keratinocyte migration. PLOS One. 2021;16(7):e0253139.
  • Nocentini A, Supuran CT. Adrenergic agonists and antagonists as antiglaucoma agents: a literature and patent review (2013–2019). Expert Opin Ther Pat. 2019;29(10):805–815.
  • Feng X, Guan W, Zhao Y, Wang C, Song M, Yao Y, Yang T, Fan H. Dexmedetomidine ameliorates lipopolysaccharide-induced acute kidney injury in rats by inhibiting inflammation and oxidative stress via the GSK-3β/Nrf2 signaling pathway. J Cell Physiol. 2019;234(10):18994–19009.
  • Yan H-X, Li W-W, Zhang Y, Wei X-W, Fu L-X, Shen G-B, Yin T, Li X-Y, Shi H-S, Wan Y, et al. Accumulation of FLT3(+) CD11c (+) dendritic cells in psoriatic lesions and the anti-psoriatic effect of a selective FLT3 inhibitor. Immunol Res. 2014;60(1):112–126.
  • Moss KG, Toner GC, Cherrington JM, Mendel DB, Laird AD. Hair depigmentation is a biological readout for pharmacological inhibition of KIT in mice and humans. J Pharmacol Exp Ther. 2003;307(2):476–480.
  • Krasnov GS, Ghukasyan LG, Abramov IS, Nasedkina TV. Determination of the subclonal tumor structure in childhood acute myeloid leukemia and acral melanoma by next-generation sequencing. Mol Biol. 2021;55(5):727–741.
  • Xu Q, He S, Yu L. Clinical benefits and safety of FMS-like tyrosine kinase 3 inhibitors in various treatment stages of acute myeloid leukemia: a systematic review, meta-analysis, and network meta-analysis. Front Oncol. 2021;11:686013.
  • Karagounis TK, Rotemberg V, Geskin LJ, Jurcic JG, Niedt G. NPM1 and FLT3-TKD mutations are enriched in patients with leukemia cutis. Dermatol Online J. 2020;26(7).
  • Brotzman N, Xu Y, Graybill A, Cocolas A, Ressler A, Seeram NP, Ma H, Henry GE. Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol. Bioorg Med Chem Lett. 2019;29(1):56–58.
  • Guy GP, Jr., Machlin SR, Ekwueme DU, Yabroff KR. Prevalence and costs of skin cancer treatment in the U.S., 2002–2006 and 2007–2011. Am J Prev Med. 2015;48(2):183–187.
  • Guy GP, Thomas CC, Thompson T, Watson M, Massetti GM, Richardson LC, Centers for Disease Control and Prevention (CDC). Vital signs: melanoma incidence and mortality trends and projections – United States, 1982–2030. MMWR Morb Mortal Wkly Rep. 2015;64(21):591–596.
  • Stern RS. Prevalence of a history of skin cancer in 2007: results of an incidence-based model. Arch Dermatol. 2010;146(3):279–282.
  • Spanbroek R, Stark HJ, Janssen-Timmen U, Kraft S, Hildner M, Andl T, Bosch FX, Fusenig NE, Bieber T, Rådmark O, et al. 5-lipoxygenase expression in Langerhans cells of normal human epidermis. Proc Natl Acad Sci U S A. 1998;95(2):663–668.
  • Katikaneni A, Jelcic M, Gerlach GF, Ma Y, Overholtzer M, Niethammer P. Lipid peroxidation regulates long-range wound detection through 5-lipoxygenase in zebrafish. Nat Cell Biol. 2020;22(9):1049–1055.
  • Mashima R, Okuyama T. The role of lipoxygenases in pathophysiology; new insights and future perspectives. Redox Biol. 2015;6:297–310.
  • Casanova ML, Blázquez C, Martínez-Palacio J, Villanueva C, Fernández-Aceñero MJ, Huffman JW, Jorcano JL, Guzmán M. Inhibition of skin tumor growth and angiogenesis in vivo by activation of cannabinoid receptors. J Clin Invest. 2003;111(1):43–50.
  • Roy T, Boateng ST, Banang-Mbeumi S, Singh PK, Basnet P, Chamcheu R-CN, Ladu F, Chauvin I, Spiegelman VS, Hill RA, et al. Identification of new fisetin analogs as kinase inhibitors: data on synthesis and anti-skin cancer activities evaluation. Data Brief. 2021;35:106858.
  • Fuhrmann F, Seichter W, Mazik M. Selective recognition of ammonium over potassium ion with acyclic receptor molecules bearing 3,4,5-trialkylpyrazolyl groups. Org Mater. 2022;4(03):61–72.
  • Polo-Cuadrado E, Acosta-Quiroga K, Rojas-Peña C, Rodriguez-Nuñez YA, Duarte Y, Brito I, Cisterna J, Gutiérrez M. Molecular modeling and structural analysis of some tetrahydroindazole and cyclopentanepyrazole derivatives as COX-2 inhibitors. Arab J Chem. 2022;15(2):103540.
  • Bartholomew GL, Carpaneto F, Sarpong R. Skeletal editing of pyrimidines to pyrazoles by formal carbon deletion. J Am Chem Soc. 2022;144(48):22309–22315.
  • Rheingold AL, Yap G, Trofimenko S. Do poly(indazolyl)borates have abnormal regiochemistry? Inorg Chem. 1995;34(4):759–760.
  • Fuse S, Suzuki K, Kuchimaru T, Kadonosono T, Ueda H, Sato S, Kizaka-Kondoh S, Nakamura H. Design, synthesis, and evaluation of indeno[2,1-c]pyrazolones for use as inhibitors against hypoxia-inducible factor (HIF)-1 transcriptional activity. Bioorg Med Chem. 2020;28(1):115207.
  • Abdelsalam EA, Zaghary WA, Amin KM, Abou Taleb NA, Mekawey AAI, Eldehna WM, Abdel-Aziz HA, Hammad SF. Synthesis and in vitro anticancer evaluation of some fused indazoles, quinazolines and quinolines as potential EGFR inhibitors. Bioorg Chem. 2019;89:102985.
  • Neumann JJ, Suri M, Glorius F. Efficient synthesis of pyrazoles: oxidative C–C/N–N bond-formation cascade. Angew Chem Int Ed Engl. 2010;49(42):7790–7794.
  • Moriya O, Urata Y, Endo T. Dehydrochlorination of hydroximic acid chlorides by the use of organotin compounds: an application for synthesis of isoxazolines and isoxazoles. J Chem Soc Chem Commun. 1991;1(1):17–18.
  • Tiwari MK, Iqubal A, Das P. Intramolecular oxidative C–N bond formation under metal-free conditions: one-pot global functionalization of pyrazole ring. Tetrahedron. 2022;126:133059.
  • Muzalevskiy VM, Rulev AY, Romanov AR, Kondrashov EV, Ushakov IA, Chertkov VA, Nenajdenko VG. Selective, metal-free approach to 3- or 5-CF3-pyrazoles: solvent switchable reaction of CF3-Ynones with hydrazines. J Org Chem. 2017;82(14):7200–7214.
  • Kolla ST, Somanaboina R, Bhimapaka CR. TBHP/Cu(OAc)2 mediated oxidation of pyrazolines: a convenient method for the preparation of pyrazoles. Synth Commun. 2021;51(9):1425–1432.
  • Zhu Y-F, Wei B-L, Wei J-J, Wang W-Q, Song W-B, Xuan L-J. Synthesis of pyrazolones and pyrazoles via Pd-catalyzed aerobic oxidative dehydrogenation. Tetrahedron Lett. 2019;60(17):1202–1205.
  • Rheinwald JG, Beckett MA. Tumorigenic keratinocyte lines requiring anchorage and fibroblast support cultured from human squamous cell carcinomas. Cancer Res. 1981;41(5):1657–1663.
  • Ma H, Johnson S, Liu W, DaSilva N, Meschwitz S, Dain J, Seeram N. Evaluation of polyphenol anthocyanin-enriched extracts of blackberry, black raspberry, blueberry, cranberry, red raspberry, and strawberry for free radical scavenging, reactive carbonyl species trapping, anti-glycation, anti-β-amyloid aggregation, and microglial neuroprotective effects. Int J Mol Sci. 2018;19(2):461.
  • Ma H, Xu J, DaSilva NA, Wang L, Wei Z, Guo L, Johnson SL, Lu W, Xu J, Gu Q, et al. Cosmetic applications of glucitol-core containing gallotannins from a proprietary phenolic-enriched red maple (Acer rubrum) leaves extract: inhibition of melanogenesis via down-regulation of tyrosinase and melanogenic gene expression in B16F10 melanoma cells. Arch Dermatol Res. 2017;309(4):265–274.
  • Gfeller D, Grosdidier A, Wirth M, Daina A, Michielin O, Zoete V. SwissTargetPrediction: a web server for target prediction of bioactive small molecules. Nucleic Acids Res. 2014;42(Web Server issue):W32–W38.
  • Meng X-Y, Zhang H-X, Mezei M, Cui M. Molecular docking: a powerful approach for structure-based drug discovery. Curr Comput Aided Drug Des. 2011;7(2):146–157.
  • Kumar Singh P, Silakari O. In silico guided development of imine-based inhibitors for resistance-deriving kinases. J Biomol Struct Dyn. 2019;37(10):2593–2599.
  • Kim S, Thiessen PA, Bolton EE, Chen J, Fu G, Gindulyte A, Han L, He J, He S, Shoemaker BA, et al. PubChem substance and compound databases. Nucleic Acids Res. 2016;44(D1):D1202–D1213.
  • O'Boyle NM, Morley C, Hutchison GR. Pybel: a Python wrapper for the OpenBabel cheminformatics toolkit. Chem Cent J. 2008;2:5.
  • O'Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR. Open Babel: an open chemical toolbox. J Cheminform. 2011;3:33.
  • Burley SK, Berman HM, Christie C, Duarte JM, Feng Z, Westbrook J, Young J, Zardecki C. RCSB Protein Data Bank: sustaining a living digital data resource that enables breakthroughs in scientific research and biomedical education. Protein Sci. 2018;27(1):316–330.
  • Harris R, Olson AJ, Goodsell DS. Automated prediction of ligand-binding sites in proteins. Proteins Struct Funct Bioinf. 2008;70(4):1506–1517.
  • Forli S, Huey R, Pique ME, Sanner MF, Goodsell DS, Olson AJ. Computational protein–ligand docking and virtual drug screening with the AutoDock suite. Nat Protoc. 2016;11(5):905–919.
  • Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem. 2010;31(2):455–461.
  • Rigsby RE, Parker AB. Using the PyMOL application to reinforce visual understanding of protein structure. Biochem Mol Biol Educ. 2016;44(5):433–437.
  • Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. 2017;7:42717.
  • Boateng ST, Roy T, Agbo ME, Banang-Mbeumi S, Chamcheu R-CN, Bramwell M, Pham LK, Jackson KE, Hill R, Nagalo BM, et al. Identification of potential inhibitors of cutaneous melanoma and non-melanoma skin cancer cells through in-vitro and in-silico screening of a small library of phenolic compounds. SSRN Electron J. 2022.
  • Liang Y, Liang B, Wu XR, Chen W, Zhao LZ. Network pharmacology-based systematic analysis of molecular mechanisms of Dingji Fumai decoction for ventricular arrhythmia. Evid Based Complement Alternat Med. 2021;2021:5535480.
  • Banerjee P, Eckert AO, Schrey AK, Preissner R. ProTox-II: a webserver for the prediction of toxicity of chemicals. Nucleic Acids Res. 2018;46(W1):W257–W263.
  • Banerjee P, Dehnbostel FO, Preissner R. Prediction is a balancing act: importance of sampling methods to balance sensitivity and specificity of predictive models based on imbalanced chemical data sets. Front Chem. 2018;6:362.

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