Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 12, 2011, Pages 3650-3658

  Benelkebir, Hanae ^a   Marie, Sabrina ^a   Hayden, Annette L ^b   Lyle, Jason ^c   Loadman, Paul M ^c   Crabb, Simon J ^b   Packham, Graham ^b   Ganesan, A ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b SOUTHAMPTON GENERAL HOSPITAL   (United Kingdom)

^c UNIVERSITY OF BRADFORD   (United Kingdom)

Author keywords

Depsipeptide; Enzyme inhibitors; Epigenetics; Histone deacetylase; Natural products

Indexed keywords

2 (TRIMETHYLSILYL)ETHYL 3 [2 [2 [2 [(TERT BUTOXY CARBONYLAMINO)METHYL]THIAZOL 4 YL] 4 METHYL 4,5 DIHYDROTHIAZOLE 4 CARBOXAMIDO]ACETOXY] 7 (TRITYLTHIO)HEPT 4 ENOATE; 2 (TRIMETHYLSILYL)ETHYL 3 [2 [[(9H FLUOREN 9 YL)METHOXY]CARBONYLAMINO]ACETOXY] 7 (TRITYLTHIO)HEPT 4 ENOATE; 2 [2 [(TERT BUTOXYCARBONYLAMINO)METHYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYLPROPANOATE; 2 [2 [1 (TERT BUTOXYCARBONYLAMINO) 2 PHENYLETHYL]THIAZOL 4 YL] 4 METHYL 4,5 DIHYDROTHIAZOLE 4 CARBOXYLIC ACID; AMINE; BENZYL DERIVATIVE; DEPSIPEPTIDE; HISTONE DEACETYLASE INHIBITOR; LARGAZOLE; LARGAZOLE DERIVATIVE; LARGAZOLE THIOL; METHYL 2 [2 [(TERT BUTOXYCARBONYLAMINO)METHYL]THIAZOLE 4 CARBOXAMIDO] 2 METHYLPROPANOATE; ROMIDEPSIN; SPIRUCHOSTATIN A; SPIRUCHOSTATIN B; SPIRUCHOSTATIN C; SPIRUCHOSTATIN D; TERT BUTYL 1 (4 CARBAMOYLTHIAZOL 2 YL) 2 PHENYLETHYLCARBAMATE; TERT BUTYL 1 (4 CYANOTHIAZOL 2 YL) 2 PHENYLETHYLCARBAMATE; THIAZOLE DERIVATIVE; THIAZOLE THIAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; CONTROLLED STUDY; DRUG HALF LIFE; DRUG MECHANISM; DRUG METABOLISM; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; LIPOPHILICITY; LIVER HOMOGENATE; MOUSE; NONHUMAN; STRUCTURAL HOMOLOGY;

ANIMALS; ANTINEOPLASTIC AGENTS; BLOTTING, WESTERN; CELL LINE, TUMOR; CELL PROLIFERATION; DEPSIPEPTIDES; DRUG STABILITY; ENZYME ACTIVATION; HELA CELLS; HISTONE DEACETYLASE INHIBITORS; HUMANS; MICE; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

MURINAE;

EID: 79958264627     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.02.024     Document Type: Article

References (55)

1. B.D. Strahl, and C.D. Allis Nature 403 2000 41
2. P. Chi, C.D. Allis, and G.G. Wang Nat. Rev. Cancer 10 2010 457
3. A. Mai, and L. Altucci Int. J. Biochem. Cell Biol. 41 2009 199
4. A. Ganesan, L. Nolan, S.J. Crabb, and G. Packham Curr. Cancer Drug Target 2 2009 963
5. A. Jüngel, C. Ospelt, and S. Gay Curr. Opin. Rheumatol. 22 2010 284
6. J.Y. Ortholand, and A. Ganesan Curr. Opin. Chem. Biol. 8 2004 271
7. A. Ganesan Curr. Opin. Biotechnol. 15 2004 584
8. A. Ganesan Curr. Opin. Chem. Biol. 12 2008 306
9. J. Rosen, J. Gottfries, S. Muresan, A. Backlund, and T.I. Oprea J. Med. Chem. 52 2009 1953
10. R.A. Bauer, J.M. Wurst, and D.S. Tan Curr. Opin. Chem. Biol. 14 2010 308
11. A.L. Harvey, R.L. Clark, S.P. Mackay, and B.F. Johnston Exp. Opin. Drug Discovery 5 2010 559
12. V. Dancik, K.P. Seiler, D.W. Young, S.L. Schreiber, and P.A. Clemons J. Am. Chem. Soc. 132 2010 9259
13. C. Choudary, C. Kumar, F. Gnad, M.L. Nielsen, M. Rehman, T.C. Walther, J.V. Olsen, and M. Mann Science 325 2009 834
14. B.N. Singh, G.H. Zhang, Y.L. Hwa, J.P. Li, S.C. Dowdy, and S.W. Jiang Exp. Rev. Anticancer 10 2010 935
15. X.J. Yang, and E. Seto Nat. Rev. Mol. Cell Biol. 9 2008 206
16. S.I. Imai, and L. Guarente Trends Pharmacol. Sci. 31 2010 212
17. X. Ma, H.H. Ezzeldin, and R.B. Diasio Drugs 69 2009 1911
18. J. Tan, S. Cang, Y. Ma, R.L. Petrillo, and D. Liu J. Hematol. Oncol. 3 2010 5
19. A. Villagra, E.M. Sotomayor, and E. Seto Oncogene 29 2010 157
20. C. Mercurio, S. Minucci, and P.G. Pelicci Pharmacol. Res. 62 2010 18
21. A. Yurek-George, F. Habens, M. Brimmell, G. Packham, and A. Ganesan J. Am. Chem. Soc. 126 2004 1030
22. S.M. Davidson, P.A. Townsend, C. Carroll, A. Yurek-George, K. Balasubramanyam, T.K. Kundu, A. Stephanou, G. Packham, A. Ganesan, and D.S. Latchman ChemBioChem 6 2005 162
23. T. Doi, Y. Iijima, K. Shin-ya, A. Ganesan, and T. Takahashi Tetrahedron Lett. 47 2006 1177
24. A. Yurek-George, A. Cecil, A.H.K. Mo, S. Wen, H. Rogers, F. Habens, S. Maeda, M. Yoshida, G. Packham, and A. Ganesan J. Med. Chem. 50 2007 5720
25. S.J. Crabb, M. Howell, H. Rogers, M. Ishfaq, A. Yurek-George, K. Carey, B.M. Pickering, P. East, R. Mitter, S. Maeda, P.W.M. Johnson, P. Townsend, K. Shin-ya, M. Yoshida, A. Ganesan, and G. Packham Biochem. Pharmacol. 76 2008 463
26. S. Wen, G. Packham, and A. Ganesan J. Org. Chem. 73 2008 9353
27. Y. Iijima, A. Munakata, K. Shin-ya, A. Ganesan, T. Doi, and T. Takahashi Tetrahedron Lett. 50 2009 2970
28. K.W. Li, W. Xing, and J.A. Simon J. Am. Chem. Soc. 118 1996 7237
29. Y. Chen, C. Gambs, Y. Abe, P. Wentworth Jr., and K.D. Janda J. Org. Chem. 68 2003 8902
30. T. Takizawa, K. Watanabe, K. Narita, T. Oguchi, H. Abe, and T. Katoh Chem. Commun. 2008 1677
31. T. Takizawa, K. Watanabe, K. Narita, K. Kudo, T. Oguchi, H. Abe, and T. Katoh Heterocycles 76 2008 275
32. T.J. Greshock, D.M. Johns, Y. Noguchi, and R.M. Williams Org. Lett. 10 2008 613
33. S. Di Maro, R.C. Pong, J.T. Hsieh, and J.M. Ahn J. Med. Chem. 51 2008 6639
34. N.A. Calandra, Y.L. Cheng, K.A. Kocak, and J.S. Miller Org. Lett. 11 2009 1971
35. K. Narita, T. Kikuchi, K. Watanabe, T. Takizawa, T. Oguchi, K. Kudo, K. Matsuhara, H. Abe, T. Yamori, M. Yoshida, and T. Katoh Chem. Eur. J. 15 2009 11174
36. K. Taori, V.J. Paul, and H. Luesch J. Am. Chem. Soc. 130 2008 1806
37. Y. Ying, K. Taori, H. Kim, J. Hong, and H. Luesch J. Am. Chem. Soc. 130 2008 8455
38. C.G. Nasveschuk, D. Ungermannova, X. Liu, and A.J. Phillips Org. Lett. 10 2008 3595
39. A. Bowers, N. West, J. Taunton, S.L. Schreiber, J.E. Bradner, and R.M. Williams J. Am. Chem. Soc. 130 2008 11219
40. A.K. Ghosh, and S. Kulkarni Org. Lett. 10 2008 3907
41. Y. Ying, Y. Liu, S.R. Byeon, H.S. Kim, H. Luesch, and J. Hong Org. Lett. 10 2008 4021
42. T. Seiser, F. Kamena, and N. Cramer Angew. Chem., Int. Ed. 47 2008 6483
43. Q. Ren, L. Dai, H. Zhang, W. Tan, Z. Xu, and T. Ye Synlett 2008 2379
44. Y. Numajiri, T. Takahashi, M. Takagi, K. Shin-ya, and T. Doi Synlett 2008 2483
45. A.A. Bowers, T.J. Greshock, N. West, G. Estiu, S.L. Schreiber, O. Wiest, R.M. Williams, and J.E. Bradner J. Am. Chem. Soc. 131 2009 2900
46. A.A. Bowers, N. West, T.L. Newkirk, A.E. Troutman-Youngman, S.L. Schreiber, O. Wiest, J.E. Bradner, and R.M. Williams Org. Lett. 11 2009 1301
47. F. Chen, A.-H. Gao, J. Li, and F.-J. Nan ChemMedChem 4 2009 1269
48. B. Wang, and C.J. Forsyth Synlett 2009 2873
49. X. Zeng, B. Yin, Z. Hu, C.Z. Liao, J.L. Liu, S. Li, Z. Li, M.C. Nicklaus, G.B. Zhou, and S. Jiang Org. Lett. 12 2010 1368
50. J.A. Souto, E. Vaz, I. Lepore, A.-C. Poppler, G. Franci, R. Alvarez, L. Altucci, and A.R. de Lera J. Med. Chem. 53 2010 4654
51. M.V.N. de Souza J. Sulfur Chem. 26 2005 429
52. P.A. Towensend, S.J. Crabb, S.M. Davidson, P.W.M. Johnson, G. Packham, and A. Ganesan S.L. Schreiber, T.M. Kapoor, G. Wess, Chemical Biology Vol. 2 2007 Wiley-VCH Weinheim 693 720
53. Z. Jin Nat. Prod. Rep. 26 2009 382
54. T.L. Newkirk, A.A. Bowers, and R.M. Williams Nat. Prod. Rep. 26 2009 1293
55. Purchased from DSM or prepared synthetically: G. Pattenden, S.M. Thom, and M.F. Jones Tetrahedron 49 1993 2131