New benzothieno[2,3-c]pyridines as non-steroidal CYP17 inhibitors: design, synthesis, anticancer screening, apoptosis induction, and in silico ADME profile studies

References

• Kaninjing ET, Dagne G, Atawodi SE, Alabi A. Modifiable risk factors implicated in prostate cancer mortality and morbidity among west African men. J Health Dispar 2019;5:1–13.
   Google Scholar
• Rafiemanesh H, Mehtarpour M, Khani F, et al. Epidemiology, incidence and mortality of lung cancer and their relationship with the development index in the world. J Thorac Dis 2016;6:1094–102.
   Google Scholar
• Carter HB, Coffey DS. The prostate: an increasing medical problem. Prostate 1990;16:39–48.
   PubMed Web of Science ®Google Scholar
• Smith R, Andrews K, Brooks D, et al. Cancer screening in the United States, 2019: a review of current American Cancer Society guidelines and current issues in cancer screening. CA Cancer J Clin 2019;69:184–210.
   PubMed Web of Science ®Google Scholar
• Halpern JA, Oromendia C, Shoag JE, et al. Use of digital rectal examination as an adjunct to prostate specific antigen in the detection of clinically significant prostate cancer. J Urol 2018;199:947–53.
   PubMed Web of Science ®Google Scholar
• Chiu PKF, Roobol MJ, Teoh JY, et al. Prostate health index (PHI) and prostate-specific antigen (PSA) predictive models for prostate cancer in the Chinese population and the role of digital rectal examination-estimated prostate volume. Int Urol Nephrol 2016;48:1631–7.
   PubMed Web of Science ®Google Scholar
• Saini S. PSA and beyond: alternative prostate cancer biomarkers. Cell Oncol 2016;39:97–106.
   PubMed Web of Science ®Google Scholar
• Chan JM, Stampfer MJ, Giovannucci EL. What causes prostate cancer? A brief summary of the epidemiology. Sem Cancer Biol 1998;8:363–273.
   Web of Science ®Google Scholar
• Nam RK, Cheung P, Herschorn S, et al. Incidence of complications other than urinary incontinence or erectile dysfunction after radical prostatectomy or radiotherapy for prostate cancer: a population-based cohort study. Lancet Oncol 2021;15:223–31.
   Google Scholar
• Sooriakumaran P, Nyberg T, Akre O, et al. Comparative effectiveness of radical prostatectomy and radiotherapy in prostate cancer: observational study of mortality outcomes. BMJ 2014;348:g1502–13.
   PubMed Web of Science ®Google Scholar
• Boevé L, Hulshof M, Vis A, et al. Effect on survival of androgen deprivation therapy alone compared to androgen deprivation therapy combined with concurrent radiation therapy to the prostate in patients with primary bone metastatic prostate cancer in a prospective randomised clinical trial: data from the HORRAD trial. Eur. Urol 2019;75:410–8.
   PubMed Web of Science ®Google Scholar
• Rusthoven CG, Jones BL, Flaig TW, et al. Improved survival with prostate radiation in addition to androgen deprivation therapy for men with newly diagnosed metastatic prostate cancer. J Clin Oncol 2016;34:2835–42.
   PubMed Web of Science ®Google Scholar
• Sun M, Choueiri TK, Hamnvik OPR, et al. Comparison of gonadotropin-releasing hormone agonists and orchiectomy: effects of androgen-deprivation therapy. JAMA Oncol 2016;2:500–7.
   PubMed Web of Science ®Google Scholar
• Shim M, Bang W, Oh C, et al. Effectiveness of three different luteinizing hormone-releasing hormone agonists in the chemical castration of patients with prostate cancer: goserelin versus triptorelin versus leuprolide. Investig Clin Urol 2019;60:244–50.
   PubMed Web of Science ®Google Scholar
• Ahmed A, Ali S, Sarkar FH. Advances in androgen receptor targeted therapy for prostate cancer. J Cell Physiol 2014;229:271–6.
   PubMed Web of Science ®Google Scholar
• Teo M, Rathkopf D, Kantoff P. Treatment of advanced prostate cancer. Annu Rev Med 2019;70:479–99.
   PubMed Web of Science ®Google Scholar
• Gillessen S, Attard G, Beer T, et al. Re: Silke Gillessen, Gerhardt Attard, Tomasz M. Beer, et al. Management of Patients with Advanced Prostate Cancer: Report of the Advanced Prostate Cancer Consensus Conference 2019. Eur Urol. 2020;77: 508-47. Eur Urol 2020;78:e201–547.
   PubMed Web of Science ®Google Scholar
• Alex AB, Pal SK, Agarwal N. CYP17 inhibitors in prostate cancer: latest evidence and clinical potential. Ther Adv Med Oncol 2016;8:267–75.
   PubMed Web of Science ®Google Scholar
• Fizazi K, Tran N, Fein L, et al. Abiraterone plus prednisone in metastatic, castration-sensitive prostate cancer. NEJM 2017;377:352–60.
   PubMed Web of Science ®Google Scholar
• Njar VC, Brodie AM. Discovery and development of Galeterone (TOK-001 or VN/124-1) for the treatment of all stages of prostate cancer. J Med Chem 2015;58:2077–87.
   PubMed Web of Science ®Google Scholar
• Bastos DA, Antonarakis ES. Galeterone for the treatment of advanced prostate cancer: the evidence to date. Drug Des Devel Ther 2016;10:2289–97.
   PubMed Web of Science ®Google Scholar
• Dellis A, Papatsoris A. Phase I and II therapies targeting the androgen receptor for the treatment of castration resistant prostate cancer. Expert Opin Invest Drugs 2016;25:697–707.
   PubMed Web of Science ®Google Scholar
• Smith MR, Saad F, Chowdhury S, et al. Apalutamide treatment and metastasis-free survival in prostate cancer. NEJM 2018;378:1408–18.
   PubMed Web of Science ®Google Scholar
• Matsunaga N, Kaku T, Itoh F, et al. C17,20-lyase inhibitors I. Structure-based de novo design and SAR study of C17,20-lyase inhibitors. Bioorg Med Chem 2004;12:2251–73.
   PubMed Web of Science ®Google Scholar
• Ideyama Y, Kudoh M, Tanimoto K, et al. Novel nonsteroidal inhibitor of cytochrome P45017α (17α‐hydroxylase/C17-20 lyase), YM116, decreased prostatic weights by reducing serum concentrations of testosterone and adrenal androgens in rats. Prostate 1998;37:10–8.
   PubMed Web of Science ®Google Scholar
• Wang M, Fang Y, Gu S, et al. Discovery of novel 1,2,3,4-tetrahydrobenzo[4,5]thieno[2,3-c]pyridine derivatives as potent and selective CYP17 inhibitors. Eur J Med Chem 2017;132:157–72.
   PubMed Web of Science ®Google Scholar
• Auchus R, Sharifi N. Sex hormones and prostate cancer. Annu Rev Med 2020;71:33–45.
   PubMed Web of Science ®Google Scholar
• Roviello G, Sigala S, Danesi R, et al. Incidence and relative risk of adverse events of special interest in patients with castration resistant prostate cancer treated with CYP-17 inhibitors: a meta-analysis of published trials. Crit Rev Oncol Hematol 2016;101:12–20.
   PubMed Web of Science ®Google Scholar
• Mouineer A, Zaher A, El-Malah A, Sobh EA. Design, synthesis, antitumor activity, cell cycle analysis and ELISA assay for cyclin dependant kinase-2 of a new (4-aryl-6-fluoro-4H-benzo[4,5]thieno[3,2-b]pyran) derivatives. Mediterr 2017;6:165–79.
   Google Scholar
• Boyd MR. The NCI human tumor cell line (60-Cell) screen. In: Anticancer drug development guide. Totowa (NJ): Humana Press; 2004:41–61.
   Google Scholar
• Boyd MR. In vitro anticancer drug discovery screen. In: Anticancer drug development guide. Totowa (NJ): Humana Press; 1997:23–42.
   Google Scholar
• Li J, Li Y, Son C, et al. 4-Pregnene-3-one-20β-carboxaldehyde: a potent inhibitor of 17α-hydroxylase/C17, 20-lyase and of 5α-reductase. J Steroid Biochem Mol Biol 1992;3:313–20.
   Google Scholar
• Shrivastav TG, Basu A, Kariya KP. One step enzyme linked immunosorbent assay for direct estimation of serum testosterone. J Immunoass Immunoch 2003;2:205–17.
   Google Scholar
• Turky A, Bayoumi AH, Ghiaty A, et al. Design, synthesis, and antitumor activity of novel compounds based on 1,2,4-triazolophthalazine scaffold: apoptosis-inductive and PCAF-inhibitory effects. Bioorg Chem 2020;101:104019.
   PubMed Web of Science ®Google Scholar
• Andree H, Reutelingsperger C, Hauptmann R, et al. Binding of vascular anticoagulant alpha (VAC alpha) to planar phospholipid bilayers. J Biol Chem 1990;265:4923–8.
   PubMed Web of Science ®Google Scholar
• Dalgliesh CE, Mann FG. The comparative reactivity of the carbonyl groups in the thionaphthenquinones. Part II. The influence of substituent groups in the thionaphthenquinones. J Chem Soc 1945;5:893–909.
   Google Scholar
• Eisa MA. Synthesis of some new fused heterocyclic rings derived from 3-benzofuranone. AREJ 2006;17:76–85.
   Google Scholar
• Wang H, Wen K, Wang L, et al. Large-scale solvent-free chlorination of hydroxy-pyrimidines, -pyridines, -pyrazines and -amides using equimolar POCl3. Molecules 2012;17:4533–44.
   PubMed Web of Science ®Google Scholar
• Joshi A, Haque N, Lateef A, et al. Apoptosis and its role in physiology. Int J Livestock Res 2017;7:33–45.
   Google Scholar
• Daina A, Zoete V. A boiled-Egg to predict gastrointestinal absorption and brain penetration of small molecules. ChemMedChem 2016;11:1117–21.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 2012;64:4–17.
   Web of Science ®Google Scholar
• 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;1:55–68.
   PubMed Web of Science ®Google Scholar
• Veber DF, Johnson SR, Cheng HY, et al. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 2002;45:2615–23.
   PubMed Web of Science ®Google Scholar
• Egan WJ, Merz KM, Baldwin JJ. Prediction of drug absorption using multivariate statistics. J Med Chem 2000;43:3867–77.
   PubMed Web of Science ®Google Scholar
• Muegge I, Heald SL, Brittelli D. Simple selection criteria for drug-like chemical matter. J Med Chem 2001;44:1841–6.
   PubMed Web of Science ®Google Scholar
• Baell JB, Holloway GA. New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays. J Med Chem 2010;53:2719–40.
   PubMed Web of Science ®Google Scholar