Design, synthesis and antiproliferative activity of 2-acetamidothiazole-5- carboxamide derivatives

Medicinal Chemistry

Volumn 8, Issue 4, 2012, Pages 587-594

  Liu, Wukun ^a,c   Zhou, Jinpei ^a   Zheng, Yu ^b   Qi, Fan ^a   Zhang, Huibin ^a   Qian, Hai ^a   Wang, Jing ^a   Cheng, Yanhua ^a   Gust, Ronald ^c,d  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b NANJING MEDICAL UNIVERSITY   (China)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

^d UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Antiproliferative activity; Dasatinib; SRC kinase inhibitor; Structure activity relationship studies; Synthesis

Indexed keywords

2 (2 (AZEPAN 1 YL)ACETAMIDO) N (4 CHLOROPHENYL)THIAZOLE 5 CARBOXAMIDE; AMIDE; DASATINIB; GEFITINIB; IMATINIB; N(4 CHLOROPHENYL) 2 (2 (4 (2 HYDROXYETHYL)PIPERAZIN 1 YL)ACETAMIDO)THIAZOLE 5 CARBOXAMIDE; N(4 CHLOROPHENYL) 2 (2 (4 METHYLPIPERAZIN 1 YL)ACETAMIDO)THIAZOLE 5 CARBOXAMIDE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMIDES; ANTINEOPLASTIC AGENTS; CARBOXYLIC ACIDS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HT29 CELLS; HUMANS; MOLECULAR STRUCTURE; NEOPLASMS; PYRIMIDINES; THIAZOLES;

EID: 84863754995     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340612801216418     Document Type: Article

References (20)

1. Kim, L. C.; Song, L.; Haura, E. B. Src kinases as therapeutic targets for cancer. Nat. Rev. Clin. Oncol., 2009, 6, 587-595.
2. Finn, R. S.; Dering, J.; Ginther, C.; Wilson, C. A.; Glaspy, P.; Tchekmedyian, N.; Slamon, D. J. Dasatinib, an orally active small molecule inhibitor of both the src and abl kinases, selectively inhibits growth of basal-type/"triple-negative" breast cancer cell lines growing in vitro. Breast Cancer Res. Tr., 2007, 105, 319-326.
3. Bauer, S.; Romvari, E. Treatment of chronic myeloid leukemia following imatinib resistance: a nursing guide to second-line treatment options. Clin. J. Oncol. Nurs., 2009, 13, 523-534.
4. Bryant, G. A once-daily dasatinib dosing strategy for chronic myeloid leukemia. Clin. J. Oncol. Nurs., 2009, 13, 316-323.
5. Fu, J.; Meng, X.; He, J.; Gu, J. Inhibition of inflammation by a p38 MAP kinase targeted cell permeable peptide. Med. Chem., 2008, 4, 597-604.
6. Hancock, C. N.; Macias, A. T.; Mackerell, Jr., A. D.; Shapiro, P. Mitogen activated protein (MAP) kinases: development of ATP and non-ATP dependent inhibitors. Med. Chem., 2006, 2, 213-222.
7. Zhang, J.; Krishnan, R.; Arnold, C. S.; Mattsson, E.; Kilpatrick, J. M.; Bantia, S.; Dehghani, A.; Boudreaux, B.; Gupta, S. N.; Kotian, P. L.; Chand, P.; Babu, Y. S. Discovery of highly potent small molecule kallikrein inhibitors. Med. Chem., 2006, 2, 545-553.
8. Quintás-Cardama, A.; Kantarjian, H.; Cortes, J. Flying under the radar: the new wave of BCR-ABL inhibitors. Nat. Rev. Drug Discov., 2007, 6, 834-848.
9. Kim, L. C.; Rix, U.; Haura, E. B. Dasatinib in solid tumors. Expert. Opin. Investig. Drugs, 2010, 19, 415-425.
10. Lombardo, L. J.; Lee, F. Y.; Chen, P.; Norris, D.; Barrish, J. C.; Behnia, K.; Castaneda, S.; Cornelius, L. A.; Das, J.; Doweyko, A. M.; Fairchild, C.; Hunt, J. T.; Inigo, I.; Johnston, K.; Kamath, A.; Kan, D.; Klei, H.; Marathe, P.; Pang, S.; Peterson, R.; Pitt, S.; Schieven, G. L.; Schmidt, R. J.; Tokarski, J.; Wen, M. L.; Wityak, J.; Borzilleri, R. M. Discovery of N-(2-chloro-6-methyl-phenyl)-2-(6-(4-(2-hydroxyethyl)-piperazin-1-yl) -2-methylpyrimidin-4-ylamino) thiazole-5-carboxamide (BMS-354825), a dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays. J. Med. Chem., 2004, 47, 6658-6661.
11. Das, J.; Chen, P.; Norris, D.; Padmanabha, R.; Lin, J.; Moquin, R. V.; Shen, Z.; Cook, L. S.; Doweyko, A. M.; Pitt, S.; Pang, S.; Shen, D. R.; Fang, Q.; de Fex, H. F.; McIntyre, K. W.; Shuster, D. J.; Gillooly, K. M.; Behnia, K.; Schieven, G. L.; Wityak, J.; Barrish, J. C. 2-Aminothiazole as a novel kinase inhibitor template. Structureactivity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2- methyl-4-pyrimidinyl]amino)]-1, 3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J. Med. Chem., 2006, 49, 6819-6831.
12. Liu, W.; Zhou, J.; Qi, F.; Bensdorf, K.; Li, Z.; Zhang, H.; Qian, H.; Huang, W.; Cai, X.; Cao, P.; Wellner, A.; Gust, R. Synthesis and biological activities of 2-amino-thiazole-5-carboxylic acid phenylamide derivatives. Arch. Pharm., 2011, 344, 451-458.
13. Lam, K. S. Application of combinatorial library methods in cancer research and drug discovery Anticancer Drug Des., 1997, 12, 145-167.
14. Chen, B. C.; Zhao, R.; Wang, B.; Droghini, R.; Lajeunesse, J.; Sirard, P.; Endo, M.; Balasubramanian, B.; Barrish, J. C. A new and efficient preparation of 2-aminothiazole-5-carbamides: applications to the synthesis of the anti-cancer drug dasatinib. Arkivoc, 2010, 32-38.
15. Chandregowda, V.; Rao, G. V.; Reddy, G. C. Convergent approach for commercial synthesis of gefitinib and erlotinib. Org. Process Res. Dev., 2007, 11, 813-816.
16. Tietze, L. F.; Schneider, C.; Pretor, M. Improved synthesis of (E)-3-alkoxy-and (E)-3-phenoxyacryloyl chlorides. Synthesis, 1993, 1079-1080.
17. Liu, W.; Zhou, J.; Bensdorf, K.; Zhang, H.; Liu, H.; Wang, Y.; Qian, H.; Zhang, Y.; Wellner, A.; Rubner, G.; Huang, W.; Guo, C.; Gust, R. Investigations on cytotoxicity and anti-inflammatory potency of licofelone derivatives. Eur. J. Med. Chem., 2011, 46, 907-913.
18. Liu, W.; Zhou, J.; Liu, Y.; Liu, H.; Bensdorf, K.; Guo, C.; Gust, R. Licofelone possessing nitric oxide donors as anticancer agents. Arch. Pharm., 2011, 344, 487-493.
19. Liao, Q. H.; Gao, Q. Z.; Wei, J.; Chou, K. C. Docking and molecular dynamics study on the inhibitory activity of novel inhibitors on epidermal growth factor receptor (EGFR). Med. Chem., 2011, 7, 24-31.
20. Fallah-Tafti, A.; Tiwari, R.; Shirazi, A. N.; Akbarzadeh, T.; Mandal, D.; Shafiee, A.; Parang, K.; Foroumadi, A. 4-Aryl-4Hchromene-3-carbonitrile derivatives: evaluation of Src kinase inhibitory and anticancer activities. Med. Chem., 2011, 7, 466-472.