Total synthesis and biological evaluation of largazole and derivatives with promising selectivity for cancers cells

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1368-1371

  Zeng, Xin ^a   Yin, Biaolin ^c   Hu, Zheng ^a,b,e   Liao, Chenzhong ^d   Liu, Jinglei ^a,b,e   Li, Shang ^a   Li, Zheng ^f   Nicklaus, Marc C ^d   Zhou, Guangbiao ^a,b,e   Jiang, Sheng ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b INSTITUTE OF ZOOLOGY   (China)

^c SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^d NATIONAL CANCER INSTITUTE   (United States)

^e UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^f HOUSTON METHODIST RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DEPSIPEPTIDE; LARGAZOLE; THIAZOLE DERIVATIVE;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; DRUG SCREENING; ENZYME SPECIFICITY; HUMAN; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THIAZOLES;

EID: 77949831890     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/01100308a     Document Type: Article

References (25)

1. (a) Newman, D. J. J. Med. Chem. 2008, 51, 2589.
2. (b) Paterson, I.; Anderson, E. A. Science 2005, 310, 451.
3. (a) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461.
4. (b) Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Chem. Rev. 2009, 109, 3012.
5. Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 1806.
6. Ying, Y.; Taori, K.; Kim, H.; Hong, J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 8455.
7. Bowers, A.; West, N.; Taunton, J.; Schreiber, S. L.; Bradner, J. E.; Williams, R. M. J. Am. Chem. Soc. 2008, 130, 11219.
8. Seiser, T.; Kamena, F.; Cramer, N. Angew. Chem., Int. Ed. 2008, 47, 1.
9. Ying, Y.; Liu, Y.; Byeon, S. R.; Kim, H.; Luesch, H.; Hong, J. Org. Lett. 2008, 10, 4021.
10. (a) Bowers, A. A.; Greshock, T. J.; West, N.; Estiu, G.; Schreiber, S. L.; Wiest, O.; Williams, R. M.; Bradner, J. E. J. Am. Chem. Soc. 2009, 131, 2900.
11. (b) Bowers, A. A.; West, N.; Newkirk, T. L.; Troutman- Youngman, A. E.; Schreiber, S. L.; Wiest, O.; Bradner, J. E.; Williams, R. M. Org. Lett. 2009, 11, 1301.
12. (a) Ghosh, A. K.; Kulkarni, S. Org. Lett. 2008, 10, 3907.
13. (b) Nasveschuk, C. G.; Ungermannova, D.; Liu, X.; Phillips, A. J. Org. Lett. 2008, 10, 3595.
14. (c) Ren, Q.; Dai, L.; Zhang, H.; Tan, W.; Xu, Z.; Ye, T. Synlett 2008, 2379.
15. (d) Numajiri, Y.; Takahashi, T.; Takagi, M.; Shin-ya, K.; Doi, T. Synlett 2008, 2483.
16. (a) Finnin, M. S.; Donigian, J. R.; Cohen, A.; Richon, V. M.; Rifkind, R. A.; Marks, P. A.; Breslow, R.; Pavletich, N. P. Nature 1999, 401, 188.
17. (b) MOE, version 2008 0; Chemical Computing Group: Montreal, Quebec, Canada, 2008.
18. (c) Macromodel 9.7; Schrodoidinger, LLC: New York, 2009.
19. Pattenden, G.; Thom, S. M.; Jones, M. F. Tetrahedron 1993, 49, 2131.
20. (a) Chiva, C.; Vilaseca, M.; Giralt, E.; Albericio, F. J. Pept. Sci. 1999, 5, 131.
21. (b) Cruz, L.; Cuevas, C.; Canedo, L. M.; Giralt, E.; Albericio, F. J. Org. Chem. 2006, 71, 3339-3344.
22. (c) Jiang, S.; Li, P.; Lee, S.-L.; Lin, C. Y.; Long, Y.-Q.; Johnson, M. D.; Dickson, R. B.; Roller, P. P. Org. Lett. 2007, 9, 9-12.
23. Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067.
24. (a) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Tetrahedron Lett. 1991, 32, 1175.
25. (b) Blackemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563.