Synthesis and antitumor evaluation of novel Benzo[d]pyrrolo[2,1-b]thiazole derivatives

European Journal of Medicinal Chemistry

Volumn 53, Issue , 2012, Pages 28-40

  Chaniyara, Ravi ^a,b   Tala, Satishkumar ^a   Chen, Chi Wei ^a,c   Lee, Pei Chih ^a   Kakadiya, Rajesh ^a   Dong, Huajin ^d   Marvania, Bhavin ^a,e   Chen, Ching Huang ^a   Chou, Ting Chao ^d   Lee, Te Chang ^a   Shah, Anamik ^b   Su, Tsann Long ^a,e  

^a INSTITUTE OF BIOMEDICAL SCIENCES   (Taiwan)

^b SAURASHTRA UNIVERSITY   (India)

^c NATIONAL YANG MING UNIVERSITY   (Taiwan)

^d MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^e CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Antitumor agents; benzo d pyrrolo 2,1 b thiazol; Cell cycle; Cytotoxicity; DNA cross linking

Indexed keywords

3 (3 CHLORO 4 FLUOROBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (3,4 DICHLOROBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (3,4 DIFLUOROBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (3,4 DIMETHOXYBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (3,4,5 TRIMETHOXYBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (4 CHLOROBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (4 FLUOROBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (4 METHOXYBENZOYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 (CYCLOPROPANECARBONYL) 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; 3 ACETYL 2,3 DIHYDROBENZO(D)THIAZOLE 2 CARBONITRILE; [1 (4 CHLOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DIYL]BIS(METHYLENE)BIS(ETHYLCARBAMATE); [1 (4 CHLOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DIYL]BIS(METHYLENE)BIS(ISO PROPYLCARBAMATE); [1 (4 FLUOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DIYL]BIS(METHYLENE)BIS(ETHYLCARBAMATE); [1 (4 FLUOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DIYL]BIS(METHYLENE)BIS(ISO PROPYLCARBAMATE); ANTINEOPLASTIC AGENT; CISPLATIN; DIMETHYL 1 (3 CHLORO 4 FLUOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; DIMETHYL 1 (3,4 DICHLOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; DIMETHYL 1 (3,4 DIMETHOXYPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; DIMETHYL 1 (3,4,5 TRIMETHOXYPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; DIMETHYL 1 (4 CHLOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; DIMETHYL 1 (4 FLUOROPHENYL)BENZO(D)PYRROLO(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; DIMETHYL 1 METHYLBENZO(D)PYRROL(2,1 B)THIAZOLE 2,3 DICARBOXYLATE; PACLITAXEL; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; VINBLASTINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BODY WEIGHT; BREAST CARCINOMA; CANCER GROWTH; CANCER INHIBITION; CANCER REGRESSION; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL CYCLE PROGRESSION; CELL CYCLE S PHASE; CELL PROLIFERATION; CHEMICAL REACTION; COLON CARCINOMA; COMPETITIVE INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DNA CROSS LINKING; DRUG EFFICACY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGENATION; IN VITRO STUDY; LUNG CARCINOMA; LYMPHATIC LEUKEMIA; MAXIMUM TOLERATED DOSE; MOUSE; MOUTH CARCINOMA; NONHUMAN; PROSTATE CARCINOMA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CHEMISTRY TECHNIQUES, SYNTHETIC; DNA; HUMANS; INHIBITORY CONCENTRATION 50; MALE; MICE; THIAZOLES; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84861586195     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.03.030     Document Type: Article

References (26)

1. S.T. Crooke S.K. Carter, S.T. Crooke, N.A. Alder, Mitomycin C. Current Status and New Development 1979 Academic Press New York
2. A.C. Satorelli Cancer Res. 48 1988 775 778
3. M. Tomasz, and Y. Palom Pharmacol. Ther. 76 1997 73 87
4. H.W. Moore, and R. Czerniak Med. Res. Rev. 3 1981 249 280
5. I.N.H. White, and A.R. Mattocks Biochem. J. 128 1972 291 297
6. W.L. Elliot, D.W. Fry, W.K. Anderson, J.M. Nelson, K.E. Hook, P.A. Hawkins, and W.R. Leopold Cancer Res. 51 1991 4581 4587
7. W.K. Anderson, and M.J. Halat J. Med. Chem. 22 1979 977 980
8. W.K. Andeson, J.S. New, and P.F. Corey Arzneim. Forsch 30 1980 765 768
9. W.K. Anderson, and R.H. Mach J. Med. Chem. 30 1987 2109 2115
10. I. Lalezari, and E.L. Schwartz J. Med. Chem. 31 1988 1427 1429
11. R. Kakadiya, H. Dong, P.C. Lee, N. Kapuriya, X. Zhang, T.C. Chou, T.C. Lee, K. Kapuriya, A. Shah, and T.L. Su Bioorg. Med. Chem. 17 2009 5614 5626
12. P.C. Lee, R. Kakadiya, T.L. Su, and T.C. Lee Neoplasia 12 2010 376 387
13. R. Chaniyara, N. Kapuriya, H. Dong, P.C. Lee, S. Suman, B. Marvania, T.C. Chou, T.C. Lee, R. Kakadiya, A. Shah, and T.L. Su Bioorg. Med. Chem. 19 2011 275 286
14. W.K. Anderson Cancer Res. 42 1982 2168 2170
15. M. Berrabah, G. Schmitt, N. Dinh, and B. Laude Bull. Soc. Chim. Belg. 100 1991 613 616
16. W.E. McEwen, I.C. Mineo, and Y.H. Shen J. Am. Chem. Soc. 93 1971 4479 4484
17. A. Pandya, and H.W. Gibson J. Org. Chem. 58 1993 2851 2855
18. C.U. Barrie, Y.P. Ho, D.S. Brown, I. Fisher, F.D. Popp, and J. Kant J. Chem. Res. Miniprint 11 1989 2652 2681
19. D.A. Scudiero, R.H. Shoemaker, K.D. Paull, A. Monks, S. Tierney, T.H. Nofziger, M.J. Currens, D. Seniff, and M.R. Boyd Cancer Res. 48 1988 4827 4833
20. P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenny, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107 1112
21. T.C. Chou, O.A. O'Connor, W.P. Tong, Y. Guan, Z.G. Zhang, S.J. Stachel, C. Lee, and S.J. Danishefsky Proc. Natl. Acad. Sci. USA 98 2001 8113 8118
22. S.A. Nasiry, M. Hanssens, C. Luyten, and R. Pijnenborn Hum. Reprod. 22 2007 1304 1309
23. T.C. Chou, and N. Martin CompuSyn Software 2005 CompuSyn Inc. Paramus, NJ (USA)
24. T.C. Chou, and P. Talalay Adv. Enzym. Regul. 22 1984 27 55
25. T.C. Chou Pharmacol. Rev. 58 2006 621 681
26. T.C. Lee, J.L. Ko, and K.Y. Jan Toxicology 56 1989 289 299