Antiproliferative benzothiazoles incorporating a trimethoxyphenyl scaffold as novel colchicine site tubulin polymerisation inhibitors

References

• Culp MB, Soerjomataram I, Efstathiou JA, et al. Recent global patterns in prostate cancer incidence and mortality rates. Eur Urol 2020;77:38–52.
   PubMed Web of Science ®Google Scholar
• Xu YH, Deng JL, Wang G, et al. Long non-coding RNAs in prostate cancer: Functional roles and clinical implications. Cancer Lett 2019;464:37–55.
   PubMed Web of Science ®Google Scholar
• Vasquez JL, Lai Y, Annamalai T, et al. Inhibition of base excision repair by natamycin suppresses prostate cancer cell proliferation. Biochimie 2020;168:241–50.
   PubMed Web of Science ®Google Scholar
• Tripathi A, Durrant D, Lee RM, et al. Hydropathic analysis and biological evaluation of stilbene derivatives as colchicine site microtubule inhibitors with anti-leukemic activity. J Enzyme Inhib Med Chem 2009;24:1237–44.
   PubMed Web of Science ®Google Scholar
• Ahmed RI, Osman EEA, Awadallah FM, et al. Design, synthesis and molecular docking of novel diarylcyclohexenone and diarylindazole derivatives as tubulin polymerization inhibitors. J Enzyme Inhib Med Chem 2017;32:176–88.
   PubMed Web of Science ®Google Scholar
• Wang G, Liu W, Gong Z, et al. Synthesis, biological evaluation, and molecular modelling of new naphthalene-chalcone derivatives as potential anticancer agents on MCF-7 breast cancer cells by targeting tubulin colchicine binding site. J Enzyme Inhib Med Chem 2020;35:139–44.
   PubMed Web of Science ®Google Scholar
• Arnst KE, Wang Y, Hwang DJ, et al. A potent, metabolically stable tubulin inhibitor targets the colchicine binding site and overcomes taxane resistance. Cancer Res 2018;78:265–77.
   PubMedGoogle Scholar
• Li W, Sun H, Xu F, et al. Synthesis, molecular properties prediction and biological evaluation of indole-vinyl sulfone derivatives as novel tubulin polymerization inhibitors targeting the colchicine binding site. Bioorg Chem 2019;85:49–59.
   PubMed Web of Science ®Google Scholar
• Bukhari SNA, Kumar GB, Revankar HM, et al. Development of combretastatins as potent tubulin polymerization inhibitors. Bioorg Chem 2017;72:130–47.
   PubMed Web of Science ®Google Scholar
• Diao PC, Lin WY, Jian XE, et al. Discovery of novel pyrimidine-based benzothiazole derivatives as potent cyclin-dependent kinase 2 inhibitors with anticancer activity. Eur J Med Chem 2019;179:196–207.
   PubMed Web of Science ®Google Scholar
• Aouad MR, Almehmadi MA, Rezki N, et al. Design, click synthesis, anticancer screening and docking studies of novel benzothiazole-1,2,3-triazoles appended with some bioactive benzofused heterocycles. J Mol Struct 2019;1188:153–64.
   Web of Science ®Google Scholar
• El-Damasy AK, Lee JH, Seo SH, et al. Design and synthesis of new potent anticancer benzothiazole amides and ureas featuring pyridylamide moiety and possessing dual B-RafV600E and C-Raf kinase inhibitory activities. Eur J Med Chem 2016;115:201–16.
   PubMed Web of Science ®Google Scholar
• Hutchinson I, Chua MS, Browne HL, et al. Antitumor Benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles. J Med Chem 2001;44:1446–55.
   PubMed Web of Science ®Google Scholar
• Hutchinson I, Bradshaw TD, Matthews CS, et al. Antitumour benzothiazoles. Part 20:††For Part 19 of the series, see ref 1. 3′-Cyano and 3′-Alkynyl-Substituted 2-(4′-Aminophenyl)benzothiazoles as new potent and selective analogues. Bioorg Med Chem Lett 2003;13:471–4.
   PubMed Web of Science ®Google Scholar
• Repicky A, Jantova S, Cipak L. Apoptosis induced by 2-acetyl-3-(6-methoxybenzothiazo)-2-yl-amino-acrylonitrile in human leukemia cells involves ROS-mitochondrial mediated death signaling and activation of p38 MAPK. Cancer Lett 2009;277:55–63.
   PubMed Web of Science ®Google Scholar
• Kamal Ä, Ashraf M, Vishnu Vardhan MVPS, et al. Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers. Bioorg Med Chem Lett 2014;24:147–51.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Yang JJ, Li P, et al. Bioactive heterocycles containing a 3,4,5-trimethoxyphenyl fragment exerting potent antiproliferative activity through microtubule destabilization. Eur J Med Chem 2018;157:50–61.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Fu L, Liu YC, et al. Structure-activity relationship studies of β-lactam-azide analogues as orally active antitumor agents targeting the tubulin colchicine site. Sci Rep 2017;7:12788.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Li P, Wu BW, et al. Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors. Eur J Med Chem 2019;165:309–22.
   PubMed Web of Science ®Google Scholar
• Arabi AA. Routes to drug design via bioisosterism of carboxyl and sulfonamide groups. Future Med Chem 2017;9:2167–2180.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Zhang SY, Liu YC, et al. Design, synthesis and antiproliferative activity studies of 1,2,3-triazole-chalcones. MedChemComm 2016;7:1664–71.
   Web of Science ®Google Scholar
• Fu DJ, Zhao RH, Li JH, et al. Molecular diversity of phenothiazines: design and synthesis of phenothiazine–dithiocarbamate hybrids as potential cell cycle blockers. Mol Divers 2017;21:933–42.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Liu JF, Zhao RH, et al. Design and antiproliferative evaluation of novel sulfanilamide derivatives as potential tubulin polymerization inhibitors. Molecules 2017;22:1470.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Zhang L, Song J, et al. Design and synthesis of formononetin-dithiocarbamate hybrids that inhibit growth and migration of PC-3cells via MAPK/Wnt signaling pathways. Eur J Med Chem 2017;127:87–99.
   PubMed Web of Science ®Google Scholar
• Fu DJ, Song J, Hou YH, et al. Discovery of 5,6-diaryl-1,2,4-triazines hybrids as potential apoptosis inducers. Eur J Med Chem 2017;138:1076–88.
   PubMed Web of Science ®Google Scholar
• Gurdal EE, Durmaz I, Cetin-Atalay R, et al. Cytotoxic activities of some benzothiazole-piperazine derivatives. J Enzyme Inhib Med Chem 2015;30:649–54.
   PubMed Web of Science ®Google Scholar
• Cindrić M, Jambon S, Harej A, et al. Novel amidino substituted benzimidazole and benzothiazole benzo[b]thieno-2-carboxamides exert strong antiproliferative and DNA binding properties. Eur J Med Chem 2017;136:468–79.
   PubMed Web of Science ®Google Scholar
• Yan J, Chen J, Zhang S, et al. Synthesis, evaluation, and mechanism study of novel indole-chalcone derivatives exerting effective antitumor activity through microtubule destabilization in vitro and in vivo. J Med Chem 2016;59:5264–83.
   PubMed Web of Science ®Google Scholar
• Cao D, Liu Y, Yan W, et al. Design, synthesis, and evaluation of in vitro and in vivo anticancer activity of 4-substituted coumarins: a novel class of potent tubulin polymerization inhibitors. J Med Chem 2016;59:5721–39.
   PubMed Web of Science ®Google Scholar
• Greene TF, Wang S, Greene LM, et al. Synthesis and biochemical evaluation of 3-phenoxy-1,4-diarylazetidin-2-ones as tubulin-targeting antitumor agents. J Med Chem 2016;59:90–113.
   PubMed Web of Science ®Google Scholar
• Luduena RF, Roach MC. Tubulin sulfhydryl groups as probes and targets for antimitotic and antimicrotubule agents. Pharmacol Ther 1991;49:133–52.
   PubMed Web of Science ®Google Scholar
• Subba Rao AV, Swapna K, Shaik SP, et al. Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers. Bioorg Med Chem 2017;25:977–99.
   PubMed Web of Science ®Google Scholar
• Bray K, Chen HY, Karp CM, et al. Bcl-2 modulation to activate apoptosis in prostate cancer. Mol Cancer Res 2009;7:1487–96.
   PubMed Web of Science ®Google Scholar