Design, synthesis, molecular modeling, DFT, ADME and biological evaluation studies of some new 1,3,4-oxadiazole linked benzimidazoles as anticancer agents and aromatase inhibitors

References

• Acar Çevik, U., Kaya Çavuşoğlu, B., Sağlık, B. N., Osmaniye, D., Levent, S., Ilgın, S., Özkay, Y., & Kaplancıklı, Z. A. (2020). Synthesis, docking studies and biological activity of new benzimidazole-triazolothiadiazine derivatives as aromatase inhibitor. Molecules, 25(7), 1642. https://doi.org/10.3390/molecules25071642
   PubMed Web of Science ®Google Scholar
• Acar Çevik, U., Sağlık, B. N., & Osmaniye, D. (2020a). Synthesis and docking study of benzimidazole–triazolothiadiazine hybrids as aromatase inhibitors. Archiv der Pharmazie, 353(5), e2000008. https://doi.org/10.1002/ardp.202000008
   PubMed Web of Science ®Google Scholar
• Acar Çevik, U., Sağlık, B. N., & Osmaniye, D. (2020b). Synthesis, anticancer evaluation and molecular docking studies of new benzimidazole-1,3,4-oxadiazole derivatives as human topoisomerase types I poison. Journal of Enzyme Inhibition and Medicinal Chemistry, 35(1), 1657–1673. https://doi.org/10.1080/14756366.2020.1806831
   PubMed Web of Science ®Google Scholar
• Ahmad, I., Jadhav, H., Shinde, Y., Jagtap, V., Girase, R., & Patel, H. (2021). Optimizing Bedaquiline for cardiotoxicity by structure based virtual screening, DFT analysis and molecular dynamic simulation studies to identify selective MDR-TB inhibitors. In Silico Pharmacology, 9(1), 23.
   PubMedGoogle Scholar
• Ahmad, I., Kumar, D., & Patel, H. (2021). Computational investigation of phytochemicals from Withania somnifera (Indian ginseng/ashwagandha) as plausible inhibitors of GluN2B-containing NMDA receptors. Journal of Biomolecular Structure and Dynamics, 10, 1–13. https://doi.org/10.1080/07391102.2021.1905553
   Google Scholar
• Ahmad, I., Shaikh, M., Surana, S., Ghosh, A., & Patel, H. (2020). p38α MAP kinase inhibitors to overcome EGFR tertiary C797S point mutation associated with osimertinib in non-small cell lung cancer (NSCLC): emergence of fourth-generation EGFR inhibitor. Journal of Biomolecular Structure and Dynamics, 11, 1–14. https://doi.org/10.1080/07391102.2020.1844801
   Google Scholar
• Akkoç, S. (2021). Design, synthesis, characterization, and in vitro cytotoxic activity evaluation of 1,2‐disubstituted benzimidazole compounds. Journal of Physical Organic Chemistry, 34(1), e4125. https://doi.org/10.1002/poc.4125
   Web of Science ®Google Scholar
• Amaral, C., Toloi, M. R. T., Vasconcelos, L. D., Fonseca, M. J. V., Correia-da-Silva, G., & Teixeira, N. (2017). The role of soybean extracts and isoflavones in hormone-dependent breast cancer: Aromatase activity and biological effects. Food & Function, 8(9), 3064–3074. https://doi.org/10.1039/C7FO00205J
   PubMed Web of Science ®Google Scholar
• Amaral, C., Varela, C. L., Mauricio, J., Sobral, A. F., Costa, S. C., Roleira, F. M., Tavares-da-Silva, E.J., Correia-da-Silvaa, G., Teixeira, N. (2017). Anti-tumor efficacy of new 7α-substituted androstanes as aromatase inhibitors in hormone-sensitive and resistant breast cancer cells. Journal of Steroid Biochemistry and Molecular Biology, 171, 218–228. https://doi.org/10.1016/j.jsbmb.2017.04.002
   Google Scholar
• Arya, G. C., Kaur, K., & Jaitak, V. (2021). Isoxazole derivatives as anticancer agent: A review on synthetic strategies, mechanism of action and SAR studies. European Journal of Medicinal Chemistry, 221, 113511. https://doi.org/10.1016/j.ejmech.2021.113511
   PubMed Web of Science ®Google Scholar
• Avvaru, S. P., Noolvi, M. N., & More, U. A. (2021). Synthesis and anticancer activity of thiadiazole containing thiourea, benzothiazole and imidazo [2,1-b][1,3,4] thiadiazole scaffolds. Medicinal Chemistry, 17, 750–765. https://doi.org/10.2174/1573406416666200519085626
   PubMed Web of Science ®Google Scholar
• Ayati, A., Moghimi, S., Toolabi, M., & Foroumadi, A. (2021). Pyrimidine-based EGFR TK inhibitors in targeted cancer therapy. European Journal of Medicinal Chemistry, 221, 113523. https://doi.org/10.1016/j.ejmech.2021.113523
   PubMed Web of Science ®Google Scholar
• Bhuvaneswari, K., Sivaguru, P., & Lalitha, A. (2020). Synthesis, anticancer evaluation, and docking studies of some novel azo chromene derivatives. Journal of the Chinese Chemical Society, 67(10), 1877–1886. https://doi.org/10.1002/jccs.201900481
   Web of Science ®Google Scholar
• Bowers, K. J., Chow, D. E., Xu, H., Dror, R. O., Eastwood, M. P., Gregersen, B. A., ... & Shaw, D. E. (2006). Scalable algorithms for molecular dynamics simulations on commodity clusters. In SC'06: Proceedings of the 2006 ACM/IEEE Conference on Supercomputing (pp. 43-43). IEEE. https://doi.org/10.1109/SC.2006.54
   Google Scholar
• Brueggemeier, R. W., Hackett, J. C., & Diaz-Cruz, E. S. (2005). Aromatase inhibitors in the treatment of breast cancer. Endocrine Reviews, 26, 331–345. https://doi.org/10.1210/er.2004-0015
   PubMed Web of Science ®Google Scholar
• Caymaz, B., Yıldız, U., Akkoç, S., Gerçek, Z., Şengül, A., & Coban, B. (2020). Synthesis, characterization, and antiproliferative activity studies of novel benzimidazole‐imidazopyridine hybrids as DNA groove binders. ChemistrySelect, 5(28), 8465–8474. https://doi.org/10.1002/slct.202001580
   Web of Science ®Google Scholar
• Çevik, U. A., Osmaniye, D., Çavuşoğlu, B. K., Sağlik, B. N., Levent, S., Ilgin, S., Can, N. Ö., Özkay, Y., & Kaplancikli, Z. A. (2019). Synthesis of novel benzimidazole–oxadiazole derivatives as potent anticancer activity. Medicinal Chemistry Research, 28(12), 2252–2261. https://doi.org/10.1007/s00044-019-02451-0
   Web of Science ®Google Scholar
• Çevik, U. A., Osmaniye, D., Levent, S., Sağlik, B. N., Çavuşoğlu, B. K., Özkay, Y., & Kaplancikl, Z. A. (2020). Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents. Heterocyclic Communications, 26(1), 6–13. https://doi.org/10.1515/hc-2020-0002
   Web of Science ®Google Scholar
• Chinnasamy, S., Selvaraj, G., Kaushik, A. C., Kaliamurthi, S., Chandrabose, S., Singh, S. K., Thirugnanasambandam, R., Gu, K., & Wei, D. Q. (2020). Molecular docking and molecular dynamics simulation studies to identify potent AURKA inhibitors: Assessing the performance of density functional theory, MM-GBSA and mass action kinetics calculations. Journal of Biomolecular Structure and Dynamics, 38(14), 4325–4335. https://doi.org/10.1080/07391102.2019.1674695
   PubMed Web of Science ®Google Scholar
• Eldehna, W. M., El Hassab, M. A., & Abo-Ashour, M. F. (2021). Development of isatin-thiazolo [3,2-a] benzimidazole hybrids as novel CDK2 inhibitors with potent in vitro apoptotic anti-proliferative activity: Synthesis, biological and molecular dynamics investigations. Bioorganic Chemistry, 110, 104748. https://doi.org/10.1016/j.bioorg.2021.104748
   PubMed Web of Science ®Google Scholar
• Ertas, M., Sahin, Z., Berk, B., Yurttas, L., Biltekin, S. N., & Demirayak, S. (2018). Pyridine‐substituted thiazolylphenol derivatives: Synthesis, modeling studies, aromatase inhibition, and antiproliferative activity evaluation. Archiv Der Pharmazie, 351(3–4), 1700272. https://doi.org/10.1002/ardp.201700272
   Web of Science ®Google Scholar
• Fantacuzzi, M., De Filippis, B., Gallorini, M., Ammazzalorso, A., Giampietro, L., Maccallini, C., … Amoroso, R. (2020). Synthesis, biological evaluation, and docking study of indole aryl sulfonamides as aromatase inhibitors. European Journal of Medicinal Chemistry, 185, 111815. https://doi.org/10.1016/j.ejmech.2019.111815
   PubMed Web of Science ®Google Scholar
• Ghorab, M. M., Alsaid, M. S., Samir, N., Abdel-Latif, G. A., Soliman, A. M., Ragab, F. A., & Abou El Ella, D. A. (2017). Aromatase inhibitors and apoptotic inducers: Design, synthesis, anticancer activity and molecular modeling studies of novel phenothiazine derivatives carrying sulfonamide moiety as hybrid molecules. European Journal of Medicinal Chemistry, 134, 304–315. https://doi.org/10.1016/j.ejmech.2017.04.028
   PubMed Web of Science ®Google Scholar
• Ghosh, D., Griswold, J., Erman, M., & Pangborn, W. (2009). Structural basis for androgen specificity and oestrogen synthesis in human aromatase. Nature, 457(7226), 219–223. https://doi.org/10.1038/nature07614
   PubMed Web of Science ®Google Scholar
• Ghosh, D., Lo, J., & Egbuta, C. (2016). Recent progress in the discovery of next generation inhibitors of aromatase from the structure–function perspective. Journal of Medicinal Chemistry, 59(11), 5131–5148. https://doi.org/10.1021/acs.jmedchem.5b01281
   PubMed Web of Science ®Google Scholar
• Husain, A., Bhutani, M., Parveen, S., Khan, S. A., Ahmad, A., & Iqbal, M. A. (2021). Synthesis, in vitro cytotoxicity, ADME, and molecular docking studies of benzimidazole‐bearing furanone derivatives. Journal of the Chinese Chemical Society, 68(2), 362–373. https://doi.org/10.1002/jccs.202000130
   Web of Science ®Google Scholar
• Jorgensen, W. L., Maxwell, D. S., & Tirado-Rives, J. (1996). Development and testing of the OPLS all atom force field on conformational energetics and properties of organic liquids. Journal of the American Chemical Society, 118(45), 11225–11236. https://doi.org/10.1021/ja9621760
   Web of Science ®Google Scholar
• Kalibaeva, G., Ferrario, M., & Ciccotti, G. (2003). Constant pressure-constant temperature molecular dynamics: A correct constrained NPT ensemble using the molecular virial. Molecular Physics, 101(6), 765–778. https://doi.org/10.1080/0026897021000044025
   Web of Science ®Google Scholar
• Khan, S. A., Asiri, A. M., Basisi, H. M., Asad, M., Zayed, M. E. M., Sharma, K., & Wani, M. Y. (2019). Synthesis and evaluation of Quinoline-3-carbonitrile derivatives as potential antibacterial agents. Bioorganic Chemistry, 88, 102968. https://doi.org/10.1016/j.bioorg.2019.102968
   PubMed Web of Science ®Google Scholar
• Martyna, G. J. (1994). Remarks on constant-temperature molecular dynamics with momentum conservation. Physical Review. E, Statistical Physics, Plasmas, Fluids, and Related Interdisciplinary Topics, 50(4), 3234–3236. https://doi.org/10.1103/physreve.50.3234
   PubMed Web of Science ®Google Scholar
• Mary, Y. S., Yalcin, G., Mary, Y. S., Resmi, K. S., Thomas, R., Önkol, T., Kasap, E. N., & Yildiz, I. (2020). Spectroscopic, quantum mechanical studies, ligand protein interactions and photovoltaic efficiency modeling of some bioactive benzothiazolinone acetamide analogs. Chemical Papers, 74(6), 1957–1958. https://doi.org/10.1007/s11696-019-01047-7
   Web of Science ®Google Scholar
• Molehin, D., Rasha, F., Rahman, R. L., & Pruitt, K. (2021). Regulation of aromatase in cancer. Molecular and Cellular Biochemistry, 476, 2449–2464. https://doi.org/10.1007/s11010-021-04099-0
   PubMed Web of Science ®Google Scholar
• Mustafa, M., El-Kardocy, A., & Mostafa, Y. A. (2021). Development of new hetero-steroid hybrids with antiproliferative activity against MCF-7 breast cancer cells. Monatshefte Für Chemie - Chemical Monthly, 152(1), 137–149. https://doi.org/10.1007/s00706-020-02716-0
   Google Scholar
• Osmaniye, D., Çelikateş, B. K., Sağlık, B. N., & Levent, S. (2021). Synthesis of some new benzoxazole derivatives and investigation of their anticancer activities. European Journal of Medicinal Chemistry, 210, 112979. https://doi.org/10.1016/j.ejmech.2020.112979
   PubMed Web of Science ®Google Scholar
• Ozcan-Sezer, S., Ince, E., Akdemir, A., Ceylan, Ö. Ö., Suzen, S., & Gurer-Orhan, H. (2019). Aromatase inhibition by 2-methyl indole hydrazone derivatives evaluated via molecular docking and in vitro activity studies. Xenobiotica, 49(5), 549–556. https://doi.org/10.1080/00498254.2018.1482029
   PubMed Web of Science ®Google Scholar
• Pawara, R., Ahmad, I., Surana, S., & Patel, H. (2021). Computational identification of 2,4-disubstituted amino-pyrimidines as L858R/T790M-EGFR double mutant inhibitors using pharmacophore mapping, molecular docking, binding free energy calculation, DFT study and molecular dynamic simulation. In Silico Pharmacology, 6(1), 54.
   Google Scholar
• Pingaew, R., Prachayasittikul, V., Anuwongcharoen, N., Prachayasittikul, S., Ruchirawat, S., & Prachayasittikul, V. (2018). Synthesis and molecular docking of N, N′-disubstituted thiourea derivatives as novel aromatase inhibitors. Bioorganic Chemistry, 79, 171–178. https://doi.org/10.1016/j.bioorg.2018.05.002
   PubMed Web of Science ®Google Scholar
• Pradhan, T., Gupta, O., Singh, G., & Monga, V. (2021). Aurora kinase inhibitors as potential anticancer agents: Recent advances. European Journal of Medicinal Chemistry, 221, 113495. https://doi.org/10.1016/j.ejmech.2021.113495
   PubMed Web of Science ®Google Scholar
• Prior, A. M., Yu, X., Park, E. J., Kondratyuk, T. P., Lin, Y., Pezzuto, J. M., & Sun, D. (2017). Structure-activity relationships and docking studies of synthetic 2-arylindole derivatives determined with aromatase and quinone reductase 1. Bioorganic and Medicinal Chemistry Letters, 27(24), 5393–5399. https://doi.org/10.1016/j.bmcl.2017.11.010
   PubMed Web of Science ®Google Scholar
• Sahay, I. I., & Ghalsasi, P. S. (2017). Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents. Synthetic Communications, 47(8), 825–834. https://doi.org/10.1080/00397911.2017.1289412
   Web of Science ®Google Scholar
• Shoombuatong, W., Schaduangrat, N., & Nantasenamat, C. (2018). Towards understanding aromatase inhibitory activity via QSAR modeling. EXCLI journal, 17, 688-708. https://doi.org/10.17179/excli2018-1417
   Google Scholar
• Srivastava, R., Gupta, S. K., Naaz, F., Sen Gupta, P. S., Yadav, M., Singh, V. K., Singh, A., Rana, M. K., Gupta, S. K., Schols, D., & Singh, R. K. (2020). Alkylated benzimidazoles: Design, synthesis, docking, DFT analysis, ADMET property, molecular dynamics and activity against HIV and YFV. Computational Biology and Chemistry, 89, 107400. https://doi.org/10.1016/j.compbiolchem.2020.107400
   PubMed Web of Science ®Google Scholar
• Trott, O., & Olson, A. J. (2010). 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
   PubMed Web of Science ®Google Scholar
• Valadares, V. S., Martins, L. C., Roman, E. A., Valente, A. P., Cino, E. A., & Moraes, A. H. (2021). Conformational dynamics of tetracenomycin aromatase/cyclase regulate polyketide binding and enzyme aggregation propensity. Biochimica et Biophysica Acta (BBA) - General Subjects, 1865(9), 129949. https://doi.org/10.1016/j.bbagen.2021.129949
   PubMed Web of Science ®Google Scholar
• Verma, S. K., Ratre, P., Jain, A. K., Liang, C., Gupta, G. D., & Thareja, S. (2021). De novo designing, assessment of target affinity and binding interactions against aromatase: Discovery of novel leads as anti-breast cancer agents. Structural Chemistry, 32(2), 847–858. https://doi.org/10.1007/s11224-020-01673-y
   Web of Science ®Google Scholar
• Wen, X., Zhou, Y., Zeng, J., & Liu, X. (2020). Recent development of 1,2,4-triazole-containing compounds as anticancer agents. Current Topics in Medicinal Chemistry, 20(16), 1441–1460. https://doi.org/10.2174/1568026620666200128143230
   PubMed Web of Science ®Google Scholar
• Zrieq, R., Ahmad, I., Snoussi, M., Noumi, E., Iriti, M., Algahtani, F. D., Patel, H., Saeed, M., Tasleem, M., Sulaiman, S., Aouadi, K., & Kadri, A. (2021). Tomatidine and Patchouli alcohol as inhibitors of SARS-CoV-2 enzymes (3CLpro, PLpro and NSP15) by molecular docking and molecular dynamics simulations. International Journal of Molecular Sciences, 22(19), 10693. https://doi.org/10.3390/ijms221910693
   PubMed Web of Science ®Google Scholar