Structure-activity relationship analysis of 3-phenylpyrazole derivatives as androgen receptor antagonists

References

• AbdulHameed, M. D., Hamza, A., Liu, J., & Zhan, C. G. (2008). Combined 3D-QSAR modeling and molecular docking study on indolinone derivatives as inhibitors of 3-phosphoinositide-dependent protein kinase-1. Journal of Chemical Information and Modeling, 48(9), 1760–1772. doi: 10.1021/ci800147v
   PubMed Web of Science ®Google Scholar
• Accelrys Discovery Studio. (2010). Version 2.5. San Diego, CA: Accelrys.
   Google Scholar
• Aggarwal, R., Beer, T. M., Gleave, M., Stuart, J. M., Rettig, M., Evans, C. P., … Small, E. J. (2016). Targeting adaptive pathways in metastatic treatment-resistant prostate cancer: Update on the stand up 2 cancer/prostate cancer foundation-supported west coast prostate cancer dream team. European Urology Focus, 2(5), 469–471. doi: 10.1016/j.euf.2016.10.011
   PubMedGoogle Scholar
• Amin, S. A., Adhikari, N., Baidya, S. K., Gayen, S., & Jha, T. (2019). Structural refinement and prediction of potential CCR2 antagonists through validated multi-QSAR modeling studies. Journal of Biomolecular Structure and Dynamics, 37(1), 75–94. doi: 10.1080/07391102.2017.1418679
   PubMed Web of Science ®Google Scholar
• Anusuya, S., & Gromiha, M. M. (2019). Structural basis of flavonoids as dengue polymerase inhibitors: Insights from QSAR and docking studies. Journal of Biomolecular Structure and Dynamics, 37(1), 104–115. doi: 10.1080/07391102.2017.1419146
   PubMed Web of Science ®Google Scholar
• Beltran, H., Beer, T. M., Carducci, M. A., de Bono, J., Gleave, M., Hussain, M., … Tannock, I. F. (2011). New therapies for castration-resistant prostate cancer: Efficacy and safety. European Urology, 60(2), 279–290. doi: 10.1016/j.eururo.2011.04.038
   PubMed Web of Science ®Google Scholar
• Bray, F., Ferlay, J., Soerjomataram, I., Siegel, R. L., Torre, L. A., & Jemal, A. (2018). Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer Journal of Clinicians, 68(6), 394–424. doi: 10.3322/caac.21492
   PubMed Web of Science ®Google Scholar
• Brinkmann, A. O., Blok, L. J., de Ruiter, P. E., Doesburg, P., Steketee, K., Berrevoets, C. A., & Trapman, J. (1999). Mechanisms of androgen receptor activation and function. Journal of Steroid Biochemistry and Molecular Biology, 69(1-6), 307–313. doi: 10.1016/S0960-0760(99)00049-7
   PubMed Web of Science ®Google Scholar
• Cabezas, F., & Mascayano, C. (2019). Docking, steered molecular dynamics, and QSAR studies as strategies for studying isoflavonoids as 5-, 12-, and 15-lipoxygenase inhibitors. Journal of Biomolecular Structure and Dynamics, 37(6), 1511–1519. doi: 10.1080/07391102.2018.1461687
   PubMed Web of Science ®Google Scholar
• Cheng, P., Li, J., Wang, J., Zhang, X., & Zhai, H. (2018). Investigations of FAK inhibitors: A combination of 3D-QSAR, docking, and molecular dynamics simulations studies. Journal of Biomolecular Structure and Dynamics, 36(6), 1529–1549. doi: 10.1080/07391102.2017.1329095
   PubMed Web of Science ®Google Scholar
• Cramer, R. D., Patterson, D. E., & Bunce, J. D. (1988). Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. Journal of the American Chemical Society, 110(18), 5959–5967. doi: 10.1021/ja00226a005
   PubMed Web of Science ®Google Scholar
• Dehm, S. M., & Tindall, D. J. (2007). Androgen receptor structural and functional elements: Role and regulation in prostate cancer. Molecular Endocrinology, 21(12), 2855–2863. doi: 10.1210/me.2007-0223
   PubMedGoogle Scholar
• Estebanez-Perpina, E., Moore, J. M., Mar, E., Delgado-Rodrigues, E., Nguyen, P., Baxter, J. D., … Guy, R. K. (2005). The molecular mechanisms of coactivator utilization in ligand-dependent transactivation by the androgen receptor. Journal of Biological Chemistry, 280(9), 8060–8068. doi: 10.1074/jbc.M407046200
   PubMed Web of Science ®Google Scholar
• Gao, C.-Z., Dong, W., Cui, Z.-W., Yuan, Q., Hu, X.-M., Wu, Q.-M., … Min, Z.-L. (2019). Synthesis, preliminarily biological evaluation and molecular docking study of new Olaparib analogues as multifunctional PARP-1 and cholinesterase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1), 150–162. doi: 10.1080/14756366.2018.1530224
   PubMed Web of Science ®Google Scholar
• Gao, W., Bohl, C. E., & Dalton, J. T. (2005). Chemistry and structural biology of androgen receptor. Chemical Reviews, 105(9), 3352–3370. doi: 10.1021/cr020456u
   PubMed Web of Science ®Google Scholar
• Gao, X., Han, L., & Ren, Y. (2016). In silico exploration of 1,7-diazacarbazole analogs as checkpoint kinase 1 inhibitors by using 3D QSAR, molecular docking study, and molecular dynamics simulations. Molecules, 21(5), 591. doi: 10.3390/molecules21050591
   Web of Science ®Google Scholar
• Gasteiger, J., & Marsili, M. (1980). Iterative partial equalization of orbital electronegativity—A rapid access to atomic charges. Tetrahedron, 36(22), 3219–3228. doi: 10.1016/0040-4020(80)80168-2
   Web of Science ®Google Scholar
• Geng, H., Xue, C., Mendonca, J., Sun, X.-X., Liu, Q., Reardon, P. N., … Qian, D. Z. (2018). Interplay between hypoxia and androgen controls a metabolic switch conferring resistance to androgen/AR-targeted therapy. Nature Communications, 9(1), 4972. doi: 10.1038/s41467-018-07411-7
   PubMedGoogle Scholar
• Guo, G., Liu, J., Wang, G., Zhang, D., Lu, J., & Zhao, G. (2016). Synthesis and biological evaluation of 3-(4-fluorophenyl)-1H-pyrazole derivatives as androgen receptor antagonists. Anticancer Drugs, 27(4), 278–285. doi: 10.1097/CAD.0000000000000322
   PubMed Web of Science ®Google Scholar
• Klebe, G., Abraham, U., & Mietzner, T. (1994). Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. Journal of Medicinal Chemistry, 37(24), 4130–4146. doi: 10.1021/jm00050a010
   PubMed Web of Science ®Google Scholar
• Lu, P., Wei, X., & Zhang, R. (2010). CoMFA and CoMSIA 3D-QSAR studies on quionolone caroxylic acid derivatives inhibitors of HIV-1 integrase. European Journal of Medicinal Chemistry, 45(8), 3413–3419. doi: 10.1016/j.ejmech.2010.04.030
   PubMed Web of Science ®Google Scholar
• Roy, P. P., Leonard, J. T., & Roy, K. (2008). Exploring the impact of size of training sets for the development of predictive QSAR models. Chemometrics & Intelligent Laboratory Systems, 90(1), 31–42. doi: 10.1016/j.chemolab.2007.07.004
   Web of Science ®Google Scholar
• Schrader, A. J., Boegemann, M., Ohlmann, C.-H., Schnoeller, T. J., Krabbe, L.-M., Hajili, T., … Cronauer, M. V. (2014). Enzalutamide in castration-resistant prostate cancer patients progressing after docetaxel and abiraterone. European Urology, 65(1), 30–36. doi: 10.1016/j.eururo.2013.06.042
   PubMed Web of Science ®Google Scholar
• Tripos. (2002). Sybyl molecular modelling software package. Version 6.9. St. Louis, MO: Tripos.
   Google Scholar
• Vora, J., Patel, S., Sinha, S., Sharma, S., Srivastava, A., Chhabria, M., & Shrivastava, N. (2019). Molecular docking, QSAR and ADMET based mining of natural compounds against prime targets of HIV. Journal of Biomolecular Structure and Dynamics, 37(1), 131–146. doi: 10.1080/07391102.2017.1420489
   PubMed Web of Science ®Google Scholar
• Wang, J., Yang, Y., Li, Y., & Wang, Y. (2016). Computational study exploring the interaction mechanism of benzimidazole derivatives as potent cattle bovine viral diarrhea virus inhibitors. Journal of Agricultural and Food Chemistry, 64(29), 5941–5950. doi: 10.1021/acs.jafc.6b01067
   PubMed Web of Science ®Google Scholar
• Wang, L., & Li, J. (2018). Structure–activity relationship analysis of carbobicyclo and oxabicyclo succinimide analogs as potential androgen receptor antagonists. Journal of Biomolecular Structure and Dynamics, 36(11), 2876–2892. doi: 10.1080/07391102.2017.1371643
   PubMed Web of Science ®Google Scholar
• Wang, J. L., Cheng, L. P., Wang, T. C., Deng, W., & Wu, F. H. (2017). Molecular modeling study of CP-690550 derivatives as JAK3 kinase inhibitors through combined 3D-QSAR, molecular docking, and dynamics simulation techniques. Journal of Molecular Graphics and Modelling, 72, 178–186. doi: 10.1016/j.jmgm.2016.12.020
   PubMed Web of Science ®Google Scholar
• Wold, S., Sjöström, M., & Eriksson, L. (2001). PLS-regression: A basic tool of chemometrics. Chemometrics & Intelligent Laboratory Systems, 58(2), 109–130. doi: 10.1016/S0169-7439(01)00155-1
   Web of Science ®Google Scholar
• Zhang, D., Asnake, S., Zhang, J., Olsson, P. E., & Zhao, G. (2018). Discovery of novel 5-methyl-1H-pyrazole derivatives as potential antiprostate cancer agents: Design, synthesis, molecular modeling, and biological evaluation. Chemical Biology & Drug Design, 91(6), 1113–1124. doi: 10.1111/cbdd.13173
   PubMed Web of Science ®Google Scholar
• Zong, Y., & Goldstein, A. S. (2013). Adaptation or selection – Mechanisms of castration-resistant prostate cancer. Nature Reviews Urology, 10(2), 90–98. doi: 10.1038/nrurol.2012.237
   PubMed Web of Science ®Google Scholar
• Zuo, K., Liang, L., Du, W., Sun, X., Liu, W., Gou, X., … Hu, J. (2017). 3D-QSAR, molecular docking and molecular dynamics simulation of Pseudomonas aeruginosa LpxC inhibitors. International Journal of Molecular Sciences, 18(5), 761. doi: 10.3390/ijms18050761
   Web of Science ®Google Scholar