Discovery of a novel class of 2-ureido thiophene carboxamide checkpoint kinase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 14, 2008, Pages 4242-4248

  Janetka, James W ^a   Almeida, Lynsie ^a   Ashwell, Susan ^a   Brassil, Patrick J ^a   Daly, Kevin ^a   Deng, Chun ^a   Gero, Thomas ^a   Glynn, Roberta E ^a   Horn, Candice L ^a   Ioannidis, Stephanos ^a   Lyne, Paul ^a   Newcombe, Nicholas J ^a   Oza, Vibha B ^a   Pass, Martin ^a   Springer, Stephanie K ^a   Su, Mei ^a   Toader, Dorin ^a   Vasbinder, Melissa M ^a   Yu, Dingwei ^a   Yu, Yan ^a   Zabludoff, Sonya D ^a   more..

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 UREIDOTHIOPHENE CARBOXAMIDE UREA; AMIDE; CHECKPOINT KINASE 1; CHECKPOINT KINASE 2; PROTEIN SERINE THREONINE KINASE; PROTEIN SERINE THREONINE KINASE INHIBITOR; THIOPHENE DERIVATIVE;

ARTICLE; CELL CYCLE G2 PHASE; DNA DAMAGE; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; METAPHASE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

AMIDES; APOPTOSIS; CARBON; CELL CYCLE; CHEMISTRY, PHARMACEUTICAL; DNA DAMAGE; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; PHENYL ETHERS; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; THIOPHENES; UREA;

EID: 47149091445     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.05.016     Document Type: Article

References (16)

1. Bucher N., and Britten C.D. Br. J. Cancer 98 (2008) 523
2. Luo Y., and Leverson J.D. Expert Rev. Anticancer Ther. 5 (2005) 333 (and references cited within)
3. Janetka J.W., Ashwell S., Zabludoff S., and Lyne P. Curr. Opin. Drug Discov. Dev. 10 (2007) 473
4. Arrington K.L., and Dudkin V.Y. ChemMedChem 2 (2007) 1571
5. Tao Z.-F., and Lin N.-H. Anti-Cancer Agents Med. Chem. 6 (2006) 377
6. Prudhomme M. Recent Patents Anti-Cancer Drug Discov. 11 (2006) 55
7. Baxter A., Brough S., Cooper A., Floettmann E., Foster S., Harding C., Kettle J., McInally T., Martin C., Mobbs M., Needham M., Newham P., Paine S., St.-Gallay S., Salter S., Unitt J., and Xue Y. Bioorg. Med. Chem. Lett. 14 (2004) 2817
8. Lyne P.D., Kenny P.W., Cosgrove D.A., Deng C., Zabludoff S., Wendoloski J.J., and Ashwell S. J. Med. Chem. 47 (2004) 1962
9. Buchstaller H.-P., Siebert C.D., Lyssy R.H., Frank I., Duran A., Gottschlich R., and Noe C.R. Monatshefte fuer Chemie 132 (2001) 279
10. Sabnis R.W., Rangnekar D.W., and Sonawane N.D. J. Heterocyclic Chem. 36 (1999) 333
11. No reaction seen even after heating with excess amine. Proposed benzotriazole ester intermediate 10b or rearranged N-oxide amide 10c: {A figure is presented}. Mahmoud K.A., Long Y.-T., Schatte G., and Kraatz H.-B. Eur. J. Inorg. Chem. 1 (2005) 173
12. Levin J.I., Turos E., and Weinreb S.M. Synth. Commun. 12 (1982) 989
13. Lipton M.F., Basha A., and Weinreb S.M. Org. Synth. 59 (1980) 49
14. Ashwell, S. Abstracts of Papers. 2007 AACR Annual Meeting, Los Angeles, CA, April 14-18, 2007.
15. Almeida, L.; Ashwell, S.; Ayres, D. W.; Brassil, P. J.; Daly, K.; Deng, C.; Gero, T.; Glynn, R. E.; Horn, C. L.; Ioannidis, S.; Janetka, J. W.; Lyne, P.; Oza, V. B.; Springer, S. K.; Su, M.; Toader, D.; Vasbinder, M. M.; Yu, D.; Yu, Y.; Zabludoff, S. D. Abstracts of Papers. 2007 EORTC-NCI-AACR International Meeting on Molecular Targets and Therapeutics, San Francisco, CA, October 22-26, 2007, p A233.
16. Ashwell, S.; Caleb, B. L.; Green, S.; Grondine, M. R.; Haye, H. R.; Horn, C. L.; Janetka, J. W.; Liu, D.; Mouchet, E.; Ready, S.; Rosenthal, J. L.; Queva, C.; Taylor, K. J.; Sheehy, A. M.; Walker, G. E.; White, A. M.; Zabludoff, S. D. Abstracts of Papers. 2007 EORTC-NCI-AACR International Meeting on Molecular Targets and Therapeutics, San Francisco, CA, October 22-26, 2007, p A232.