New styrylquinoxaline: synthesis, structural, biological evaluation, ADMET prediction and molecular docking investigations

References

• Aakeröy, C. B., Wijethunga, T. K., & Desper, J. (2015). Molecular electrostatic potential dependent selectivity of hydrogen bonding. New Journal of Chemistry, 39(2), 822–828. https://doi.org/10.1039/C4NJ01324G
   Web of Science ®Google Scholar
• Abad, N., Lgaz, H., Atioglu, Z., Akkurt, M., Mague, J. T., Ali, I. H., Chung, I.-M., Salghi, R., Essassi, E. M., & Ramli, Y. (2020). Synthesis, crystal structure, hirshfeld surface analysis, DFT computations and molecular dynamics study of 2-(benzyloxy)-3-phenylquinoxaline. Journal of Molecular Structure, 1221, 128727. https://doi.org/10.1016/j.molstruc.2020.128727
   Web of Science ®Google Scholar
• Abad, N., Sallam, H. H., Al-Ostoot, F. H., Khamees, H. A., Al-Horaibi, S. A., A, S. M., Khanum, S. A., Madegowda, M., Hafi, M. E., Mague, J. T., Essassi, E. M., & Ramli, Y. (2021). Synthesis, crystal structure, DFT calculations, Hirshfeld surface analysis, energy frameworks, molecular dynamics and docking studies of novel isoxazolequinoxaline derivative (IZQ) as anti-cancer drug. Journal of Molecular Structure, 1232, 130004. https://doi.org/10.1016/j.molstruc.2021.130004
   Web of Science ®Google Scholar
• Abdel-Rahman, L. H., Basha, M. T., Al-Farhan, B. S., Shehata, M. R., Mohamed, S. K., & Ramli, Y. (2022). [Cu(dipicolinoylamide)(NO3)(H2O)] as anti-COVID-19 and antibacterial drug candidate: Design, synthesis, crystal structure, DFT and molecular docking. Journal of Molecular Structure, 1247, 131348. https://doi.org/10.1016/j.molstruc.2021.131348
   PubMed Web of Science ®Google Scholar
• Aihara, J. (2000). Correlation found between the HOMO–LUMO energy separation and the chemical reactivity at the most reactive site for isolated-pentagon isomers of fullerenes. Physical Chemistry Chemical Physics, 2(14), 3121–3125. https://doi.org/10.1039/b002601h
   Web of Science ®Google Scholar
• Averbukh, I., Ben-Zvi, D., Mishra, S., & Barkai, N. (2014). Scaling morphogen gradients during tissue growth by a cell division rule. Development (Cambridge, England), 141(10), 2150–2156. https://doi.org/10.1242/dev.107011
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A: General Physics, 38(6), 3098–3100. https://doi.org/10.1103/physreva.38.3098
   PubMedGoogle Scholar
• Bhat, M., Zinjarde, S. S., Bhargava, S. Y., Kumar, A. R., & Joshi, B. N. (2011). Antidiabetic indian plants: A good source of potent amylase inhibitors, evidence-based complement. Evidence-Based Complementary and Alternative Medicine, 2011, 1–6. https://doi.org/10.1093/ecam/nen040
   Google Scholar
• Blaak, E. E., Antoine, J.-M., Benton, D., Björck, I., Bozzetto, L., Brouns, F., Diamant, M., Dye, L., Hulshof, T., Holst, J. J., Lamport, D. J., Laville, M., Lawton, C. L., Meheust, A., Nilson, A., Normand, S., Rivellese, A. A., Theis, S., Torekov, S. S., & Vinoy, S. (2012). Impact of postprandial glycaemia on health and prevention of disease. Obesity Reviews, 13(10), 923–984. https://doi.org/10.1111/j.1467-789X.2012.01011.x
   PubMed Web of Science ®Google Scholar
• Bouyahya, A., Lagrouh, F., Omari, N. E., Bourais, I., Jemli, M. E., Marmouzi, I., Salhi, N., Faouzi, M. E. A., Belmehdi, O., Dakka, N., & Bakri, Y. (2020). Essential oils of Mentha viridis rich phenolic compounds show important antioxidant, antidiabetic, dermatoprotective, antidermatophyte and antibacterial properties. Biocatalysis and Agricultural Biotechnology, 23, 101471. https://doi.org/10.1016/j.bcab.2019.101471
   Web of Science ®Google Scholar
• Bruker. (2016). Apex3, Saint, Sadabs & Shelxtl. Bruker AXS, Inc.
   Google Scholar
• Chen, J., Li, L., Zhou, X., Li, B., Zhang, X., & Hui, R. (2018). Structural characterization and α-glucosidase inhibitory activity of polysaccharides extracted from Chinese traditional medicine Huidouba. International Journal of Biological Macromolecules, 117, 815–819. https://doi.org/10.1016/j.ijbiomac.2018.05.192
   PubMed Web of Science ®Google Scholar
• Chinnam, P., Mohsin, M., & Shafee, L. M. (2012). Evaluation of acute toxicity of pioglitazone in mice. Toxicology International, 19(3), 250–254. https://doi.org/10.4103/0971-6580.103660
   PubMedGoogle Scholar
• Cruz, J. V., Neto, M. F A., Silva, L. B., da, R., Ramos, S., da, J., Costa, S., Brasil, D. S B., Lobato, C. C., da Costa, G. V., Bittencourt, J. A. H. M., da Silva, C. H. T P., Leite, F. H. A., & Santos, C. B. R. (2018). Identification of novel protein kinase receptor type 2 inhibitors using pharmacophore and structure-based virtual screening. Molecules, 23(2), 453. 23020453. https://doi.org/10.3390/molecules
   PubMed Web of Science ®Google Scholar
• Dennington, R., Keith, T., & Millam, J. (2009). Gauss View, Version 5. https://www.scirp.org/(S(vtj3fa45qm1ean45vvffcz55)).
   Google Scholar
• Dewangan, D., Nakhate, K. T., Verma, V. S., Nagori, K., Badwaik, H., Nair, N., Tripathi, D. K., & Mishra, A. (2018). Synthesis and molecular docking study of novel hybrids of 1,3,4‐oxadiazoles and quinoxaline as a potential analgesic and anti-inflammatory agents. Journal of Heterocyclic Chemistry, 55(12), 2901–2910. https://doi.org/10.1002/jhet.3363
   Web of Science ®Google Scholar
• Ditchfield, R. (1972). Molecular orbital theory of magnetic shielding and magnetic susceptibility. Journal of Chemical Physics, 56(11), 5688–5691. https://doi.org/10.1063/1.1677088
   Web of Science ®Google Scholar
• Dos Santos, C. B. R., da, R., Ramos, S., Ortiz, B. L. S., da Silva, G. M., Giuliatti, S., Balderas-Lopez, J. L., Navarrete, A., & Carvalho, J. C. T. (2018). Oil from the fruits of Pterodon emarginatus Vog.: A traditional anti-inflammatory. Study combining in vivo and in silico. Journal of Ethnopharmacology, 222, 107–120. https://doi.org/10.1016/j.jep.2018.04.041
   PubMed Web of Science ®Google Scholar
• Fleming, I., & Wiley, J. (1979). Frontier orbitals and organic chemical reactions. Journal of Molecular Structure, 56, 306. https://doi.org/10.1016/0022-2860(79)80172-6
   Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Jr., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J., & Fox, D. J. (2010). Gaussian 09. Wallingford, CT: Gaussian, Inc.
   Google Scholar
• Fujisawa, T., Ikegami, H., Inoue, K., Kawabata, Y., & Ogihara, T. (2005). Effect of two alpha-glucosidase inhibitors, voglibose and acarbose, on postprandial hyperglycemia correlates with subjective abdominal symptoms. Metabolism: Clinical and Experimental, 54(3), 387–390. https://doi.org/10.1016/j.metabol.2004.10.004
   PubMed Web of Science ®Google Scholar
• Ghose, A., & Viswanadhan, V. (2001). Tools for designing diverse, druglike, cost-effective combinatorial libraries. Combinatorial Library Design and Evaluation, 321–356. https://doi.org/10.1201/9781482270761-16
   Google Scholar
• Gilman, J. J. (2007). Bond modulus and stability of covalent solids. Philosophical Magazine Letters, 87(2), 121–124. https://doi.org/10.1080/09500830601166974
   Web of Science ®Google Scholar
• Guerrab, W., Jemli, M. E., Akachar, J., Demirtaş, G., Mague, J. T., Taoufik, J., Ibrahimi, A., Ansar, M., Alaoui, K., & Ramli, Y. (2021). Design, synthesis, structural and molecular characterization, toxicity, psychotropic activity and molecular docking evaluation of a novel phenytoin derivative: 3-decyl-5,5-diphenylimidazolidine-2,4-dione. Journal of Biomolecular Structure and Dynamics. https://doi.org/10.1080/07391102.2021.1922096
   Google Scholar
• Hashim, A., Khan, M. S., Khan, M. S., Baig, M. H., & Ahmad, S. (2013). Antioxidant and α-amylase inhibitory property of Phyllanthus virgatus L.: An in vitro and molecular interaction study. BioMed Research International, 2013, 729393–729312. https://doi.org/10.1155/2013/729393
   PubMed Web of Science ®Google Scholar
• Hinsberg, O. (1887). Ueber Chinoxalinbasen, Justus Liebig’s Ann. Justus Liebig's Annalen Der Chemie, 237(3), 327–372. https://doi.org/10.1002/jlac.18872370305
   Google Scholar
• Ibrahim, M. K., Eissa, I. H., Abdallah, A. E., Metwaly, A. M., Radwan, M. M., & ElSohly, M. A. (2017). Design, synthesis, molecular modeling and anti-hyperglycemic evaluation of novel quinoxaline derivatives as potential PPARγ and SUR agonists. Bioorganic & Medicinal Chemistry, 25(4), 1496–1513. https://doi.org/10.1016/j.bmc.2017.01.015
   PubMed Web of Science ®Google Scholar
• International Diabetes Federation. ( 2019). IDF diabetes atlas (9th ed.). International Diabetes Federation. https://idf.org/ aboutdiabetes/what-is-diabetes/facts-figures.html.
   Google Scholar
• Jayaram, B., Singh, T., Mukherjee, G., Mathur, A., Shekhar, S., & Shekhar, V. (2012). Sanjeevini: a freely accessible web-server for target directed lead molecule discovery. BMC Bioinformatics, 13(Suppl 17), S7. https://doi.org/10.1186/1471-2105-13-S17-S7
   PubMed Web of Science ®Google Scholar
• Kee, K. T., Koh, M., Oong, L. X., & Ng, K. (2013). Screening culinary herbs for antioxidant and α-glucosidase inhibitory activities. International Journal of Food Science & Technology, 48(9), 1884–1891. https://doi.org/10.1111/ijfs.12166
   Web of Science ®Google Scholar
• Khaldan, A., Bouamrane, S., En-Nahli, F., El-Mernissi, R., El Khatabi, K., Hmamouchi, R., Maghat, H., Ajana, M. A., Sbai, A., Bouachrine, M., & Lakhlifi, T. (2021). Prediction of potential inhibitors of SARS-CoV-2 using 3D-QSAR, molecular docking modeling and ADMET properties. Heliyon, 7(3), e06603. https://doi.org/10.1016/j.heliyon.2021.e06603
   PubMed Web of Science ®Google Scholar
• Khan, I., Panini, P., Khan, SU-D., Rana, U. A., Andleeb, H., Chopra, D., Hameed, S., & Simpson, J. (2016). Exploiting the role of molecular electrostatic potential, deformation density, topology, and energetics in the characterization of S···N and Cl···N supramolecular motifs in crystalline triazolothiadiazoles. Crystal Growth and Design, 16(3), 1371–1386. https://doi.org/10.1021/acs.cgd.5b01499
   Web of Science ®Google Scholar
• Khan, M. S., Munawar, M. A., Ashraf, M., Alam, U., Ata, A., Asiri, A. M., Kousar, S., & Khan, M. A. (2014). Synthesis of novel indenoquinoxaline derivatives as potent α-glucosidase inhibitors. Bioorganic & Medicinal Chemistry, 22(3), 1195–1200. https://doi.org/10.1016/j.bmc.2013.12.024
   PubMed Web of Science ®Google Scholar
• Kitchen, D. B., Decornez, H., Furr, J. R., & Bajorath, J. (2004). Docking and scoring in virtual screening for drug discovery: Methods and applications. Nature Reviews Drug Discovery, 3(11), 935–949. https://doi.org/10.1038/nrd1549
   PubMed Web of Science ®Google Scholar
• Kramer, C., Ting, A., Zheng, H., Hert, J., Schindler, T., Stahl, M., Robb, G., Crawford, J. J., Blaney, J., Montague, S., Leach, A. G., Dossetter, A. G., & Griffen, E. J. (2018). Learning medicinal chemistry absorption, distribution, metabolism, excretion, and toxicity (ADMET) rules from cross-company matched molecular pairs analysis (MMPA). Journal of Medicinal Chemistry, 61(8), 3277–3292. https://doi.org/10.1021/acs.jmedchem.7b00935
   PubMed Web of Science ®Google Scholar
• Lee, C., Yang, W., & Parr, R. G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Physical Review B: Condensed Matter, 37(2), 785–789. https://doi.org/10.1103/physrevb.37.785
   PubMed Web of Science ®Google Scholar
• Liu, J., Shang, F., Yang, Z., Wu, M., & Zhao, J. (2017). Structural analysis of a homogeneous polysaccharide from Achatina fulica. International Journal of Biological Macromolecules, 98, 786–792. https://doi.org/10.1016/j.ijbiomac.2017.01.149
   PubMed Web of Science ®Google Scholar
• Liu, W., Hu, C., Liu, Y., Dai, S., Lu, W., Lv, X., Yao, W., & Gao, X. (2017). Preparation, characterization, and α-glycosidase inhibition activity of a carboxymethylated polysaccharide from the residue of Sarcandra glabra (Thunb.) Nakai. International Journal of Biological Macromolecules, 99, 454–464. https://doi.org/10.1016/j.ijbiomac.2017.02.065
   PubMed Web of Science ®Google Scholar
• Luo, Y.-H., & Sun, B.-W. (2013). Pharmaceutical co-crystals of pyrazinecarboxamide (PZA) with various carboxylic acids: Crystallography, hirshfeld surfaces, and dissolution study. Crystal Growth and Design, 13(5), 2098–2106. https://doi.org/10.1021/cg400167w
   Web of Science ®Google Scholar
• Missioui, M., Essassi, E. M., Mague, J. T., & Ramli, Y. (2020). Synthesis and crystal structure of (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one, C24H20N2O2. Zeitschrift Für Kristallographie – New Crystal Structures, 235(6), 1323–1325. https://doi.org/10.1515/ncrs-2020-0300
   Web of Science ®Google Scholar
• Missioui, M., Mortada, S., Guerrab, W., Serdaroğlu, G., Kaya, S., Mague, J. T., Essassi, E. M., Faouzi, M. E. A., & Ramli, Y. (2021). Novel antioxidant quinoxaline derivative: Synthesis, crystal structure, theoretical studies, antidiabetic activity and molecular docking study. Journal of Molecular Structure, 1239, 130484. https://doi.org/10.1016/j.molstruc.2021.130484
   Web of Science ®Google Scholar
• Missioui, M., Said, M. A., Demirtaş, G., Mague, J. T., & Ramli, Y. (2022). Docking of disordered independent molecules of novel crystal structure of (N-(4-methoxyphenyl)-2-(3-methyl-2-oxo-3,4-dihydroquinoxalin-1(2H)-yl)acetamide as anti-COVID-19 and anti-Alzheimer’s disease. Crystal structure, HSA/DFT/XRD. Journal of Molecular Structure, 1247, 131420. https://doi.org/10.1016/j.molstruc.2021.131420
   Web of Science ®Google Scholar
• Missioui, M., Said, M. A., Demirtaş, G., Mague, J. T., Al-Sulami, A., Al-Kaff, N. S., & Ramli, Y. (2022). A possible potential COVID-19 drug candidate: Diethyl 2-(2-(2-(3-methyl-2-oxoquinoxalin-1(2H)-yl)acetyl)hydrazono)malonate: Docking of disordered independent molecules of a novel crystal structure, HSA/DFT/XRD and cytotoxicity. Arabian Journal of Chemistry, 15(2), 103595. https://doi.org/10.1016/j.arabjc.2021.103595
   PubMed Web of Science ®Google Scholar
• Nair, S. S., Kavrekar, V., & Mishra, A. (2013). In vitro studies on alpha amylase and alpha glucosidase inhibitory activities of selected plant extracts. European Journal of Experimental Biology, 3(1), 128–132. www.pelagiaresearchlibrary.com.
   Google Scholar
• Nimse, S. B., & Pal, D. (2015). Free radicals, natural antioxidants, and their reaction mechanisms. RSC Advances, 5(35), 27986–28006. https://doi.org/10.1039/C4RA13315C
   Web of Science ®Google Scholar
• Noblía, P., Vieites, M., Torre, M. H., Costa-Filho, A. J., Cerecetto, H., González, M., Lavaggi, M. L., Adachi, Y., Sakurai, H., & Gambino, D. (2006). Novel vanadyl complexes with quinoxaline N(1),N(4)-dioxide derivatives as potent in vitro insulin-mimetic compounds . Journal of Inorganic Biochemistry, 100(2), 281–287. https://doi.org/10.1016/j.jinorgbio.2005.11.012
   PubMed Web of Science ®Google Scholar
• OECD. (2002). Guidance Document on Acute Oral Toxicity Testing. OECD. https://doi.org/10.1787/9789264078413-en
   Google Scholar
• Oprea, T. I. (2000). Property distribution of drug-related chemical databases. Journal of Computer-Aided Molecular Design, 14(3), 251–264. https://doi.org/10.1023/A:1008130001697.
   PubMed Web of Science ®Google Scholar
• Patel, H. M., Bhardwaj, V., Sharma, P., Noolvi, M. N., Lohan, S., Bansal, S., & Sharma, A. (2019). Quinoxaline-PABA bipartite hybrid derivatization approach: Design and search for antimicrobial agents. Journal of Molecular Structure, 1184, 562–568. https://doi.org/10.1016/j.molstruc.2019.02.074
   Web of Science ®Google Scholar
• Pavia, D. L., Lampman, G. M., Kriz, G. S., & Vyvyan, J. R. (2009). Introduction to Spectroscopy. Cengage Learning.
   Google Scholar
• Prabakaran, G., Manivarman, S., & Bharanidharan, M. (2020). Catalytic synthesis, ADMET, QSAR and molecular modeling studies of novel chalcone derivatives as highly potent antioxidant agents.  Journal of Xidian University, 14, 85-106. https://doi.org/10.1016/j.matpr.2020.11.166
   Google Scholar
• Putz, H., & Brandenburg, K. (2012). Diamond – Crystal and molecular structure visualization. Putz, H., & Brandenburg, K. (2012). Diamond - Crystal and Molecular Structure Visualization Crystal Impact.
   Google Scholar
• Ramli, Y., & Essassi, E. M. (2015). Advances in synthetic approaches, functionnalization and biological properties of quinoxaline derivatives. In J. C. Taylor (Ed.), Advances in Chemistry Research (Vol. 27, pp. 109–160). Nova Science Publishers.
   Google Scholar
• Ramli, Y., Moussaif, A., Karrouchi, K., & Essassi, E. M. (2014). Pharmacological profile of quinoxalinone. Journal of Chemistry, 2014, 1–21. https://doi.org/10.1155/2014/563406
   Web of Science ®Google Scholar
• Ramos, R. S., Macêdo, W. J. C., Costa, J. S., de, C. H. T., da Silva, P., Rosa, J. M C., da Cruz, J. N., de Oliveira, M. S., de Aguiar Andrade, E. H., Silva, R. B. L. e., Souto, R. N. P., & Santos, C. B. R. (2020). Potential inhibitors of the enzyme acetylcholinesterase and juvenile hormone with insecticidal activity: Study of the binding mode via docking and molecular dynamics simulations. Journal of Biomolecular Structure and Dynamics, 38(16), 4687–4709. https://doi.org/10.1080/07391102.2019.1688192
   PubMed Web of Science ®Google Scholar
• Ramos, R., Costa, J., Silva, R., da Costa, G., Rodrigues, A., Rabelo, É., Souto, R., Taft, C., Silva, C., Rosa, J., Santos, C., & Macêdo, W. (2019). Identification of potential inhibitors from pyriproxyfen with insecticidal activity by virtual screening. Pharmaceuticals, 12(1), 20. https://doi.org/10.3390/ph12010020
   Web of Science ®Google Scholar
• Roig-Zamboni, V., Cobucci-Ponzano, B., Iacono, R., Ferrara, M. C., Germany, S., Bourne, Y., Parenti, G., Moracci, M., & Sulzenbacher, G. (2017). Structure of human lysosomal acid α-glucosidase – A guide for the treatment of Pompe disease. Nature Communication, 8(1), 1111. https://doi.org/10.1038/s41467-017-01263-3.
   PubMed Web of Science ®Google Scholar
• Saleem, U., Amin, S., Ahmad, B., Azeem, H., Anwar, F., & Mary, S. (2017). Acute oral toxicity evaluation of aqueous ethanolic extract of Saccharum munja Roxb. roots in albino mice as per OECD 425 TG. Toxicology Reports, 4, 580–585. https://doi.org/10.1016/j.toxrep.2017.10.005
   PubMed Web of Science ®Google Scholar
• Salhi, N., Bouyahya, A., El-Goumari, O., Jemly, M. E., Bourais, I., Zellou, A., Cherrah, Y., & Faouzi, M. E. A. (2020). Investigation of in vitro and in vivo antioxidant and antidiabetic activities of Pinus halepensis extracts. Journal of Herbmed Pharmacology, 10(1), 123–131. https://doi.org/10.34172/jhp.2021.13
   Google Scholar
• Saravana Mani, K., Murugesapandian, B., Kaminsky, W., & Rajendran, S. P. (2018). Enantioselective approach towards the synthesis of spiro-indeno [1,2-b] quinoxaline pyrrolothiazoles as antioxidant and antiproliferative. Tetrahedron Letters, 59(30), 2921–2929. https://doi.org/10.1016/j.tetlet.2018.06.035
   Web of Science ®Google Scholar
• Seth, S. K., Maity, G. C., & Kar, T. (2011). Structural elucidation, Hirshfeld surface analysis and quantum mechanical study of para-nitro benzylidene methyl arjunolate. Journal of Molecular Structure, 1000(1–3), 120–126. https://doi.org/10.1016/j.molstruc.2011.06.003
   Web of Science ®Google Scholar
• Sheldrick, G. M. (2009). TWINABS. University of Göttingen.
   Google Scholar
• Sheldrick, G. M. (2015a). Crystal structure refinement with SHELXL. Acta Crystallographic Section C: Structural Chemistry, 71(Part 1), 3–8. https://doi.org/10.1107/S2053229614024218
   PubMedGoogle Scholar
• Sheldrick, G. M. (2015b). SHELXT—integrated space-group and crystal-structure determination. Acta Crystallographica Section A: Foundations and Advances, 71(Part 1), 3–8. https://doi.org/10.1107/S2053273314026370
   PubMedGoogle Scholar
• Shen, Q.-K., Gong, G.-H., Li, G., Jin, M., Cao, L.-H., & Quan, Z.-S. (2020). Discovery and evaluation of novel synthetic 5-alkyl-4-oxo-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoxaline-1-carbox-amide derivatives as anti-inflammatory agents. Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1), 85–95. https://doi.org/10.1080/14756366.2019.1680658
   PubMed Web of Science ®Google Scholar
• Spectragryph – Optical spectroscopy software: Licenses/Pricing. (n.d.). https://www.effemm2.de/spectragryph/license.html.
   Google Scholar
• Srinivasarao, S., Nandikolla, A., Suresh, A., Ewa, A.-K., Głogowska, A., Ghosh, B., Kumar, B. K., Murugesan, S., Pulya, S., Aggarwal, H., & Sekhar, KVGC. (2020). Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents. Bioorganic Chemistry, 100, 103955. https://doi.org/10.1016/j.bioorg.2020.103955
   PubMed Web of Science ®Google Scholar
• Tarpada, U. P., Thummar, B. B., & Raval, D. K. (2017). A green protocol for the synthesis of quinoxaline derivatives catalyzed by polymer supported sulphanilic acid. Arabian Journal of Chemistry, 10, S2902–S2907. 021. https://doi.org/10.1016/j.arabjc.2013.11
   Web of Science ®Google Scholar
• Tighadouini, S., Roby, O., Mortada, S., Lakbaibi, Z., Radi, S., Al-Ali, A., Faouzi, M. E. A., Ferbinteanu, M., Garcia, Y., Al-Zaqri, N., Zarrouk, A., & Warad, I. (2022). Crystal structure, physicochemical, DFT, optical, keto-enol tautomerization, docking, and anti-diabetic studies of (Z)-pyrazol β-keto-enol derivative. Journal of Molecular Structure, 1247, 131308. https://doi.org/10.1016/j.molstruc.2021.131308
   Web of Science ®Google Scholar
• Trott, O., & Olson, A. J. (2009). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461. https://doi.org/10.1002/jcc.21334.
   Web of Science ®Google Scholar
• van Breemen, R. B., & Li, Y. (2005). Caco-2 cell permeability assays to measure drug absorption. Expert Opinion on Drug Metabolism & Toxicology, 1(2), 175–185. https://doi.org/10.1517/17425255.1.2.175
   PubMedGoogle Scholar
• Venhorst, J., ter Laak, A. M., Commandeur, J. N. M., Funae, Y., Hiroi, T., & Vermeulen, N. P. E. (2003). Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities. Journal of Medicinal Chemistry, 46(1), 74–86. https://doi.org/10.1021/jm0209578
   PubMed Web of Science ®Google Scholar
• Weng, L., Chen, T.-H., Zheng, Q., Weng, W.-H., Huang, L., Lai, D., Fu, Y.-S., & Weng, C.-F. (2021). Syringaldehyde promoting intestinal motility with suppressing α-amylase hinders starch digestion in diabetic mice. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 141, 111865. https://doi.org/10.1016/j.biopha.2021.111865
   PubMed Web of Science ®Google Scholar
• Williams, L. K., Li, C., Withers, S. G., & Brayer, G. D. (2012). Order and disorder: Differential structural impacts of myricetin and ethyl caffeate on human amylase, an antidiabetic target. Journal of Medicinal Chemistry, 55(22), 10177–10186. https://doi.org/10.1021/jm301273u
   PubMed Web of Science ®Google Scholar
• Williams, P. A., Cosme, J., Ward, A., Angove, H. C., Matak Vinković, D., & Jhoti, H. (2003). Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature, 424(6947), 464–468. https://doi.org/10.1038/nature01862
   PubMed Web of Science ®Google Scholar
• Wolff, D. S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., & Spackman, J. M. A. (2012). CrystalExplorer (Version 3. 1). University of Westestern Australia. https://doi.org/10.1039/b704980c
   Google Scholar
• Wolinski, K., Hinton, J. F., & Pulay, P. (1990). Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112(23), 8251–8260. https://doi.org/10.1021/ja00179a005
   Web of Science ®Google Scholar
• Wu, J. Q., Kosten, T. R., & Zhang, X. Y. (2013). Free radicals, antioxidant defense systems, and schizophrenia. Progress in Neuro-Psychopharmacology & Biological Psychiatry, 46, 200–206. https://doi.org/10.1016/j.pnpbp.2013.02.015
   PubMed Web of Science ®Google Scholar
• Xiong, G., Wu, Z., Yi, J., Fu, L., Yang, Z., Hsieh, C., Yin, M., Zeng, X., Wu, C., Lu, A., Chen, X., Hou, T., & Cao, D. (2021). ADMETlab 2.0: An integrated online platform for accurate and comprehensive predictions of ADMET properties. Nucleic Acids Research, 49(W1), W5–W14. https://doi.org/10.1093/nar/gkab255
   PubMed Web of Science ®Google Scholar
• Yadava, U., Gupta, D. K., & Roychoudhury, M. (2010). Theoretical investigations on molecular structure and IR frequencies of 4-n-nonyl-4′-cyanobiphenyl in light of experimental results. Journal of Molecular Liquids, 156(2–3), 187–190. https://doi.org/10.1016/j.molliq.2010.06.002
   Web of Science ®Google Scholar
• Yadava, U., Yadav, S. K., & Yadav, R. K. (2017a). Electronic structure, vibrational assignments and simulation studies with A/T rich DNA duplex of an aromatic bis-amidine derivative. DNA Repair, 60, 9–17. https://doi.org/10.1016/j.dnarep.2017.10.005
   PubMed Web of Science ®Google Scholar
• Yadava, U., Yadav, V. K., & Yadav, R. K. (2017b). Novel anti-tubulin agents from plant and marine origins: Insight from a molecular modeling and dynamics study. RSC Advances, 7(26), 15917–15925. https://doi.org/10.1039/C7RA00370F
   Web of Science ®Google Scholar
• Yan, A., Wang, Z., & Cai, Z. (2008). Prediction of human intestinal absorption by GA feature selection and support vector machine regression. International Journal of Molecular Sciences, 9(10), 1961–1976. https://doi.org/10.3390/ijms9101961
   PubMed Web of Science ®Google Scholar
• Zaoui, Y., Ramli, Y., Tan, S. L., Tiekink, E. R. T., Chemlal, L., Mague, J. T., Taoufik, J., Faouzi, M. E. A., & Ansar, M. (2021). Synthesis, structural characterisation and theoretical studies of a novel pyridazine derivative: Investigations of anti-inflammatory activity and inhibition of α-glucosidase. Journal of Molecular Structure, 1234, 130177. https://doi.org/10.1016/j.molstruc.2021.130177
   Web of Science ®Google Scholar
• Zhang, H., Zhang, L., Gao, C., Yu, R., & Kang, C. (2021). Pharmacophore screening, molecular docking, ADMET prediction and MD simulations for identification of ALK and MEK potential dual inhibitors. Journal of Molecular Structure, 1245, 131066. https://doi.org/10.1016/j.molstruc.2021.131066
   Web of Science ®Google Scholar
• Zheng, C.-B., Gao, W.-C., Pang, P.-P., Ma, X., Peng, L.-C., Yang, L., & Li, X. (2021). Synthesis and vasorelaxant evaluation of novel 7-methoxyl-2,3-disubstituted-quinoxaline derivatives. Bioorganic & Medicinal Chemistry Letters, 36, 127785. https://doi.org/10.1016/j.bmcl.2021.127785
   PubMed Web of Science ®Google Scholar