Synthesis and biological assessment of indole derivatives containing penta-heterocycles scaffold as novel anticancer agents towards A549 and K562 cells

References

• Yahya EB, Alqadhi AM. Recent trends in cancer therapy: a review on the current state of gene delivery. Life Sci. 2021;269:119087.
   PubMed Web of Science ®Google Scholar
• You WP, Henneberg M. Cancer incidence increasing globally: the role of relaxed natural selection. Evol Appl. 2018;11(2):140–152.
   PubMed Web of Science ®Google Scholar
• Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2018;68(6):394–424.
   PubMed Web of Science ®Google Scholar
• Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I, Jemal A, Bray F. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 2021;71(3):209–249.
   PubMed Web of Science ®Google Scholar
• Bansal A, Saleh-E-In MM, Kar P, Roy A, Sharma NR. Synthesis of carvacrol derivatives as potential new anticancer agent against lung cancer. Molecules. 2022;27(14):4597.
   PubMed Web of Science ®Google Scholar
• Meggendorfer M, Haferlach T, Alpermann T, Jeromin S, Haferlach C, Kern W, Schnittger S. Specific molecular mutation patterns delineate chronic neutrophilic leukemia, atypical chronic myeloid leukemia, and chronic myelomonocytic leukemia. Haematologica. 2014;99(12):e244–e246.
   PubMed Web of Science ®Google Scholar
• Ali R, Mirza Z, Ashraf GMD, Kamal MA, Ansari SA, Damanhouri GA, Abuzenadah AM, Chaudhary AG, Sheikh IA. New anticancer agents: recent developments in tumor therapy. Anticancer Res. 2012;32(7):2999–3005.
   PubMed Web of Science ®Google Scholar
• Zhou X, Liu J, Meng J, Fu Y, Wu Z, Ouyang G, Wang Z. Discovery of facile amides-functionalized rhodanine-3-acetic acid derivatives as potential anticancer agents by disrupting microtubule dynamics. J Enzyme Inhib Med Chem. 2021;36(1):1996–2009.
   PubMed Web of Science ®Google Scholar
• Kumar V, Kaur K, Gupta GK, Sharma AK. Pyrazole containing natural products: synthetic preview and biological significance. Eur J Med Chem. 2013;69:735–753.
   PubMed Web of Science ®Google Scholar
• Minnelli C, Laudadio E, Sorci L, Sabbatini G, Galeazzi R, Amici A, Semrau MS, Storici P, Rinaldi S, Stipa P, et al. Identification of a novel nitroflavone-based scaffold for designing mutant-selective EGFR tyrosine kinase inhibitors targeting T790M and C797S resistance in advanced NSCLC. Bioorg Chem. 2022;129:106219.
   PubMed Web of Science ®Google Scholar
• Park H, Jung H-Y, Mah S, Hong S. Discovery of EGFR(d746-750/T790M/C797S) mutant-selective inhibitors via structure-based de novo design. Angew Chem Int Ed Engl. 2017;56(26):7634–7638.
   PubMed Web of Science ®Google Scholar
• Han Y, Dong W, Guo Q, Li X, Huang L. The importance of indole and azaindole scaffold in the development of antitumor agents. Eur J Med Chem. 2020;203:112506.
   PubMed Web of Science ®Google Scholar
• Dhuguru J, Skouta R. Role of indole scaffolds as pharmacophores in the development of Anti-lung cancer agents. Molecules. 2020;25(7):1615.
   PubMed Web of Science ®Google Scholar
• More KN, Hong VS, Lee A, Park J, Kim S, Lee J. Discovery and evaluation of 3,5-disubstituted indole derivatives as pim kinase inhibitors. Bioorg Med Chem Lett. 2018;28(14):2513–2517.
   PubMed Web of Science ®Google Scholar
• Dadashpour S, Emami S. Indole in the target-based design of anticancer agents: a versatile scaffold with diverse mechanism. Eur J Med Chem. 2018;150:9–29.
   PubMed Web of Science ®Google Scholar
• Koca İ, Özgür A, Coşkun KA, Tutar Y. Synthesis and anticancer activity of acyl thioureas bearing pyrazole moiety. Bioorg Med Chem. 2013;21(13):3859–3865.
   PubMed Web of Science ®Google Scholar
• Elbastawesy MAI, Aly AA, Ramadan M, Elshaier YAMM, Youssif BGM, Brown AB, El-Din A Abuo-Rahma G. Novel pyrazoloquinolin-2-ones: design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors. Bioorg Chem. 2019;90:103045.
   PubMed Web of Science ®Google Scholar
• Ahadi H, Shokrzadeh M, Hosseini-Khah Z, Ghassemi Barghi N, Ghasemian M, Emadi E, Zargari M, Razzaghi-Asl N, Emami S. Synthesis and biological assessment of ciprofloxacin-derived 1,3,4-thiadia-zoles as anticancer agents. Bioorg Chem. 2020;105:104383.
   PubMed Web of Science ®Google Scholar
• Nafie MS, Boraei ATA. Exploration of novel VEGFR2 tyrosine kinase inhibitors via design and synthesis of new alkylated indolyl-triazole schiff bases for targeting breast cancer. Bioorg Chem. 2022;122:105708.
   PubMed Web of Science ®Google Scholar
• Pallis AG, Serfass L, Dziadziusko R, van Meerbeeck JP, Fennell D, Lacombe D, Welch J, Gridelli C. Targeted therapies in the treatment of advanced/metastatic NSCLC. Eur J Cancer. 2009;45(14):2473–2487. − 
   PubMed Web of Science ®Google Scholar
• Ramalingam SS, Owonikoko TK, Khuri FR. Lung cancer: new biological insights and recent therapeutic advances. CA Cancer J Clin. 2011;61(2):91–112. − 
   PubMed Web of Science ®Google Scholar
• Zheng D, Wang R, Ye T, Yu S, Hu H, Shen X, Li Y, Ji H, Sun Y, Chen H, et al. MET exon 14 skipping defines a unique molecular class of non-small cell lung cancer. Oncotarget. 2016;7(27):41691–41702. − 
   PubMedGoogle Scholar
• Shangary S, Wang SM. Small-molecule inhibitors of the MDM2-p53 protein-protein interaction to reactivate p53 function: a novel approach for cancer therapy. Annu Rev Pharmacol Toxicol. 2009;49:223–241.
   PubMed Web of Science ®Google Scholar
• Bykov VJN, Issaeva N, Shilov A, Hultcrantz M, Pugacheva E, Chumakov P, Bergman J, Wiman KG, Selivanova G. Restoration of the tumor suppressor function to mutant p53 by a low-molecular-weight compound. Nat Med. 2002;8(3):282–288.
   PubMed Web of Science ®Google Scholar
• Issaeva N, Bozko P, Enge M, Protopopova M, Verhoef LGGC, Masucci M, Pramanik A, Selivanova G. Small molecule RITA binds to p53, blocks p53-HDM-2 interaction and activates p53 function in tumors. Nat Med. 2004;10(12):1321–1328.
   PubMed Web of Science ®Google Scholar
• Vassilev LT. MDM2 inhibitors for cancer therapy. Trends Mol Med. 2007;13(1):23–31.
   PubMed Web of Science ®Google Scholar
• Wiman KG. Strategies for therapeutic targeting of the p53 pathway in cancer. Cell Death Differ. 2006;13(6):921–926.
   PubMed Web of Science ®Google Scholar
• Vassilev LT, Vu BT, Graves B, Carvajal D, Podlaski F, Filipovic Z, Kong N, Kammlott U, Lukacs C, Klein C, et al. In vivo activation of the p53 pathway by small-molecule antagonists of MDM2. Science. 2004;303(5659):844–848.
   PubMed Web of Science ®Google Scholar
• Ding K, Lu Y, Nikolovska-Coleska Z, Qiu S, Ding Y, Gao W, Stuckey J, Krajewski K, Roller PP, Tomita Y, et al. Structure-based design of potent non-peptide MDM2 inhibitors. J Am Chem Soc. 2005;127(29):10130–10131.
   PubMed Web of Science ®Google Scholar
• Shangary S, Qin D, McEachern D, Liu M, Miller RS, Qiu S, Nikolovska-Coleska Z, Ding K, Wang G, Chen J, et al. Temporal activation of p53 by a specific MDM2 inhibitor is selectively toxic to tumors and leads to complete tumor growth inhibition. Proc Natl Acad Sci U S A. 2008;105(10):3933–3938.
   PubMed Web of Science ®Google Scholar
• Yan L, Li Y, Deng M, Chen A, Du Z, Dong C, Chen H. Design, synthesis and biological activities of compounds containing 1,3,4-oxadiazole or 1,3,4-thiadiazole. Chin J Org Chem. 2020;40(3):731–739.
   Web of Science ®Google Scholar
• Zhang Y, Wang Q, Li L, Le Y, Liu L, Yang J, Li Y, Bao G, Yan L. Synthesis and preliminary structure-activity relationship study of 3-methylquinazolinone derivatives as EGFR inhibitors with enhanced antiproliferative activities against tumor cells. J Enzyme Inhib Med Chem. 2021;36(1):1205–1216.
   PubMed Web of Science ®Google Scholar
• Le Y, Gan Y, Fu Y, Liu J, Li W, Zou X, Zhou Z, Wang Z, Ouyang G, Yan L, et al. Design, synthesis and in vitro biological evaluation of quinazolinone derivatives as EGFR inhibitors for antitumor treatment. J Enzyme Inhib Med Chem. 2020;35(1):555–564.
   PubMed Web of Science ®Google Scholar
• Shao L-H, Fan S-L, Meng Y-F, Gan Y-Y, Shao W-B, Wang Z-C, Chen D-P, Ouyang G-P. Design, synthesis, biological activities and 3D-QSAR studies of quinazolinone derivatives containing hydrazone structural units. New J Chem. 2021;45(10):4626–4631.
   Web of Science ®Google Scholar
• Zhao N, Tian K-T, Cheng K-G, Han T, Hu X, Li D-H, Li Z-L, Hua H-M. Antiproliferative activity and apoptosis inducing effects of nitric oxide donating derivatives of evodiamine. Bioorg Med Chem. 2016;24(13):2971–2978.
   PubMed Web of Science ®Google Scholar
• Grada A, Otero-Vinas M, Prieto-Castrillo F, Obagi Z, Falanga V. Research techniques made simple: analysis of collective cell migration using the wound healing assay. J Invest Dermatol. 2017;137(2):e11–e16.
   PubMed Web of Science ®Google Scholar
• Friedl P, Wolf K. Tumour-cell invasion and migration: diversity and escape mechanisms. Nat Rev Cancer. 2003;3(5):362–374.
   PubMed Web of Science ®Google Scholar
• Abou-Zied HA, Youssif BGM, Mohamed MFA, Hayallah AM, Abdel-Aziz M. EGFR inhibitors and apoptotic inducers: design, synthesis, anticancer activity, and docking studies of novel xanthine derivatives carrying chalcone moiety as hybrid molecules. Bioorg Chem. 2019;89:102997.
   PubMed Web of Science ®Google Scholar
• Hisham M, Youssif BGM, Osman EEA, Hayallah AM, Abdel-Aziz M. Synthesis, and biological evaluation of novel xanthine derivatives as potential apoptotic antitumor agents. Eur J Med Chem. 2019;176:117–128.
   PubMed Web of Science ®Google Scholar
• Wang S, Zhao Y, Aguilar A, Bernard D, Yang C-Y. Targeting the MDM2-p53 protein-protein interaction for new cancer therapy: progress and challenges. Cold Spring Harb Perspect Med. 2017;7(5):a026245.
   PubMed Web of Science ®Google Scholar
• Slaett J, Romero I, Bergman J. Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride. Synthesis. 2004;16:2760–2765.
   Google Scholar
• El-Mekabaty A, Etman HA, Mosbah A. Synthesis of some new fused pyrazole derivatives bearing indole moiety as antioxidant agents. J Heterocyclic Chem. 2016;53(3):894–900.
   Web of Science ®Google Scholar
• Kaftory M, Botoshansky M, Sheinin Y. Dimormorphism and cocrystal formation of 3-(chloroacetamido)pyrazole. Crystal Growth & Design. 2005;5(6):2242–2247.
   Web of Science ®Google Scholar
• Chen X, Gan X, Chen J, Chen Y, Wang Y, Hu D, Song B. Synthesis and Nematicidal activity of novel 1,3,4-oxadiazole (thiadiazole)thioether derivatives containing trifluorobuten moiety. Chin J Org Chem. 2017;37(9):2343–2351.
   Web of Science ®Google Scholar
• Altıntop M, Ciftci H, Radwan M, Sever B, Kaplancıklı Z, Ali T, Koga R, Fujita M, Otsuka M, Özdemir A, et al. Design, synthesis, and biological evaluation of novel 1,3,4-thiadiazole derivatives as potential antitumor agents against chronic myelogenous leukemia: striking effect of nitrothiazole moiety. Molecules. 2017;23(1):59–75.
   PubMed Web of Science ®Google Scholar
• Yang C, Yang S, Song BA, et al. Synthesis and antifungal activity of 2-substituted sulfinyl (sulfonyl)-5-(4-nitro or 4-methoxyphenyl)-1,3,4-thiadiazole derivatives. Chin J Org Chem. 2010;30:1327–1334.
   Web of Science ®Google Scholar
• Sami AA, Thoraya AF, Magdi EAZ, et al. Discovery of novel indolyl-1,2,4-triazole hybrids as potent vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors with potential anti-renal cancer activity. Bioorg Chem. 2020;105:104330.
   PubMed Web of Science ®Google Scholar
• Mathew V, Giles D, Keshavayya J, Vaidya VP. Studies on synthesis and pharmacological activities of 1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles and their dihydro analogues. Arch Pharm (Weinheim)). 2009;342(4):210–222.
   PubMed Web of Science ®Google Scholar
• Yun C-H, Boggon TJ, Li Y, Woo MS, Greulich H, Meyerson M, Eck MJ. Structures of lung cancer-derived EGFR mutants and inhibitor complexes: mechanism of activation and insights into differential inhibitor sensitivity. Cancer Cell. 2007;11(3):217–227.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Seeliger D, Groot BL. Ligand docking and binding site analysis with PyMOL and Autodock/Vina. J Comput Aided Mol Des. 2010;24(5):417–422.
   PubMed Web of Science ®Google Scholar
• Ravindranath PA, Forli S, Goodsell DS, Olson AJ, Sanner MF. AutoDockFR: advances in protein-ligand docking with explicitly specified binding site flexibility. PLoS Comput Biol. 2015;11(12):e1004586.
   PubMed Web of Science ®Google Scholar
• Mohamed FAM, Gomaa HAM, Hendawy OM, Ali AT, Farghaly HS, Gouda AM, Abdelazeem AH, Abdelrahman MH, Trembleau L, Youssif BGM, et al. Design, synthesis, and biological evaluation of novel EGFR inhibitors containing 5-chloro-3-hydroxymethyl-indole-2-scarboxamide scaffold with apoptotic antiproliferative activity. Bioorg Chem. 2021;112:104960.
   PubMed Web of Science ®Google Scholar