Design, synthesis and biological evaluation of some novel benzothiazole/benzoxazole and/or benzimidazole derivatives incorporating a pyrazole scaffold as antiproliferative agents

Bioorganic Chemistry - Tập 74 - Trang 82-90 - 2017
Mohamed A. Abdelgawad1,2, Rania B. Bakr1,2, Hany A. Omar3,4
1Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt
2Department of Pharmaceutical Chemistry, College of Pharmacy, Aljouf University, Sakaka, Aljouf 2014, Saudi Arabia
3Sharjah Institute for Medical Research, College of Medicine, University of Sharjah, Sharjah, United Arab Emirates
4Department of Pharmacology, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt

Tài liệu tham khảo

Hamidpour, 2014, Chemistry, pharmacology, and medicinal property of sage (salvia) to prevent and cure illnesses such as obesity, diabetes, depression, dementia, lupus, autism, heart disease, and cancer, J. Tradit. Complement. Med., 4, 82, 10.4103/2225-4110.130373 Doucas, 2006, Basic principles of the molecular biology of cancer I, Surgery (Oxford), 24, 43, 10.1383/surg.2006.24.2.43 S. Mukherjee, The emperor of all maladies: a biography of cancer, Simon and Schuster, 2010. Jemal, 2008, Cancer statistics, 2008, CA: Cancer J. Clin., 58, 71 Jemal, 2010, Cancer statistics, 2010, CA: Cancer J. Clin., 60, 277 Subbaramaiah, 2003, Cyclooxygenase 2: a molecular target for cancer prevention and treatment, Trends Pharmacol. Sci., 24, 96, 10.1016/S0165-6147(02)00043-3 Dempke, 2001, Cyclooxygenase-2: a novel target for cancer chemotherapy?, J. Cancer Res. Clin. Oncol., 127, 411, 10.1007/s004320000225 Ristimنki, 2002, Prognostic significance of elevated cyclooxygenase-2 expression in breast cancer, Cancer Res., 62, 632 Dannenberg, 2003, Targeting cyclooxygenase-2 in human neoplasia: rationale and promise, Cancer Cell, 4, 431, 10.1016/S1535-6108(03)00310-6 Eberhart, 1994, Up-regulation of cyclooxygenase 2 gene expression in human colorectal adenomas and adenocarcinomas, Gastroenterology, 107, 1183, 10.1016/0016-5085(94)90246-1 Harris, 2002, Prostaglandins as modulators of immunity, Trends Immunol., 23, 144, 10.1016/S1471-4906(01)02154-8 R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents, Nature 384 (1996) 384. Park, 1997, Cyclooxygenase-2 is expressed in bladder during fetal development and stimulated by outlet obstruction, Am. J. Physiol. – Renal Physiol., 273, F538, 10.1152/ajprenal.1997.273.4.F538 Gupta, 2001, Colorectal cancer prevention and treatment by inhibition of cyclooxygenase-2, Nat. Rev. Cancer, 1, 11, 10.1038/35094017 Moussa, 2008, Novel role of thromboxane receptors β isoform in bladder cancer pathogenesis, Cancer Res., 68, 4097, 10.1158/0008-5472.CAN-07-6560 Kirschenbaum, 2001, The role of cyclooxygenase-2 in prostate cancer, Urology, 58, 127, 10.1016/S0090-4295(01)01255-9 Hussain, 2003, Cyclooxygenase-2 and prostate carcinogenesis, Cancer Lett., 191, 125, 10.1016/S0304-3835(02)00524-4 Soslow, 2000, COX-2 is expressed in human pulmonary, colonic, and mammary tumors, Cancer, 89, 2637, 10.1002/1097-0142(20001215)89:12<2637::AID-CNCR17>3.0.CO;2-B Tian, 1997, Endothelial PAS domain protein 1 (EPAS1), a transcription factor selectively expressed in endothelial cells, Genes Dev., 11, 72, 10.1101/gad.11.1.72 Grِsch, 2001, COX-2 independent induction of cell cycle arrest and apoptosis in colon cancer cells by the selective COX-2 inhibitor celecoxib, FASEB J., 15, 2742, 10.1096/fj.01-0299fje Reddy, 2000, Chemoprevention of colon cancer by specific cyclooxygenase-2 inhibitor, celecoxib, administered during different stages of carcinogenesis, Cancer Res., 60, 293 Dang, 2004, Phase II study of celecoxib and trastuzumab in metastatic breast cancer patients who have progressed after prior trastuzumab-based treatments, Clin. Cancer Res., 10, 4062, 10.1158/1078-0432.CCR-03-0463 Patel, 2005, Celecoxib inhibits prostate cancer growth: evidence of a cyclooxygenase-2-independent mechanism, Clin. Cancer Res., 11, 1999, 10.1158/1078-0432.CCR-04-1877 Bouabdallah, 2006, Anticancer effect of three pyrazole derivatives, Nat. Product Res., 20, 1024, 10.1080/14786410600921441 Nitulescu, 2010, Synthesis of new pyrazole derivatives and their anticancer evaluation, Eur. J. Med. Chem., 45, 4914, 10.1016/j.ejmech.2010.07.064 Kumar, 2013, Pyrazole scaffold: a remarkable tool in the development of anticancer agents, Eur. J. Med. Chem., 70, 248, 10.1016/j.ejmech.2013.10.004 K. Ando, K. Kawamura, Sulfamoylheleroaryl Pyrazole Compounds as Anti-Inflammatory/Analgesic Agents, Google Patents, 2003. Amir, 2005, Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of 3, 5-dimethyl pyrazoles, 3-methyl pyrazol-5-ones and 3,5-disubstituted pyrazolines, Indian J. Chem., 44B, 2532 A.A. Farghaly, A.A. Bekhit, J. Young Park, Design and synthesis of some oxadiazolyl, thiadiazolyl, thiazolidinyl, and thiazolyl derivatives of 1H‐pyrazole as anti‐inflammatory antimicrobial agents, Archiv der Pharmazie 333 (2000) 53–57. Bakr, 2016, Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1-phenylpyrazolo [3, 4-d]pyrimidine derivatives, J. Enzyme Inhib. Med. Chem., 31, 6, 10.1080/14756366.2016.1186018 Abdellatif, 2017, Nitric oxide-NASIDS donor prodrugs as hybrid safe anti-inflammatory agents, Curr. Top. Med. Chem., 17, 941, 10.2174/1568026616666160927153435 Lv, 2010, Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents, Bioorgan. Med. Chem., 18, 4606, 10.1016/j.bmc.2010.05.034 Aiello, 2008, Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3, 4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)(1), J. Med. Chem., 51, 5135, 10.1021/jm800418z Shi, 1996, Antitumor benzothiazoles. 3. 1 Synthesis of 2-(4-aminophenyl) benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo, J. Med. Chem., 39, 3375, 10.1021/jm9600959 Huang, 2006, Synthesis and anticancer evaluation of bis (benzimidazoles), bis (benzoxazoles), and benzothiazoles, Bioorg. Med. Chem., 14, 6106, 10.1016/j.bmc.2006.05.007 Xiang, 2012, Novel benzothiazole, benzimidazole and benzoxazole derivatives as potential antitumor agents: synthesis and preliminary in vitro biological evaluation, Molecules, 17, 873, 10.3390/molecules17010873 Oksuzoglu, 2008, Some benzoxazoles and benzimidazoles as DNA topoisomerase I and II inhibitors, J. Enzyme Inhib. Med. Chem., 23, 37, 10.1080/14756360701342516 Hutchinson, 2002, Antitumor benzothiazoles. 16. 1 Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl) benzothiazole amino acid prodrugs, J. Med. Chem., 45, 744, 10.1021/jm011025r Mortimer, 2006, Antitumor benzothiazoles. 26. 1 2-(3, 4-dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines, J. Med. Chem., 49, 179, 10.1021/jm050942k Yamauchi, 2008, Facile synthesis of (2-benzimidazolyl)-1-azaazulenes, (2-benzothiazolyl)-1-azaazulenes, and related compounds and evaluation of their anticancer in vitro activity, Heterocycles, 76, 617, 10.3987/COM-08-S(N)53 Abdelgawad, 2013, Synthesis Anti-breast cancer activity, and molecular modeling of some benzothiazole and benzoxazole derivatives, Archiv der Pharmazie, 346, 534, 10.1002/ardp.201300044 Abdellatif, 2014, Synthesis and anticancer activity of some new pyrazolo[3, 4-d]pyrimidin-4-one derivatives, Molecules, 19, 3297, 10.3390/molecules19033297 Abdelgawad, 2016, Design, synthesis and antitumor activity of novel pyrazolo [3, 4-d] pyrimidine derivatives as EGFR-TK inhibitors, Bioorg. Chem., 66, 88, 10.1016/j.bioorg.2016.03.011 Abdellatif, 2014, Synthesis, docking study and antitumor evaluation of certain newly synthesized pyrazolo[3, 4-d]pyrimidine derivatives, Org. Chem.: Indian J., 10, 157 Bakr, 2016, (3, 5-Dimethylpyrazol-1-yl)-[4-(1-phenyl-1H-pyrazolo [3, 4-d] pyrimidin-4-ylamino) phenyl] methanone, Molbank, 2016, M915, 10.3390/M915 Abdellatif, 2017, Synthesis, EGFR inhibition and anti-cancer activity of new 3, 6-dimethyl-1-phenyl-4-(substituted-methoxy) pyrazolo [3, 4-d] pyrimidine derivatives, Anti-Cancer Agents Med. Chem., 10.2174/1872211311666170213105004 Chua, 1999, Antitumor benzothiazoles. 7. Synthesis of 2-(4-acylaminophenyl) benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines, J. Med. Chem., 42, 381, 10.1021/jm981076x Omar, 2013, OSU-A9 inhibits angiogenesis in human umbilical vein endothelial cells via disrupting Akt–NF-κB and MAPK signaling pathways, Toxicol. Appl. Pharmacol., 272, 616, 10.1016/j.taap.2013.07.014 Belal, 2017, New benzothiazole/benzoxazole-pyrazole hybrids with potential as COX inhibitors: design, synthesis and anticancer activity evaluation, Res. Chem. Intermed., 43, 3859, 10.1007/s11164-016-2851-x