Design, synthesis, and biological evaluation of conformationally constrained glycerol 3-phosphate acyltransferase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 17, 2010, Pages 6470-6479

  Wydysh, Edward A ^a   Vadlamudi, Aravinda ^b   Medghalchi, Susan M ^b   Townsend, Craig A ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b FASgen Inc   (United States)

Author keywords

Glycerol 3 phosphate acyltransferase; GPAT; Obesity; Triacylglycerol

Indexed keywords

2 (NONYLSULFONAMIDO)BENZOIC ACID; 2 [2 HYDROXY 3 (OCTYLSULFONAMIDO)CYCLOHEXYL]ACETIC ACID; 2 [2 HYDROXY 3 (OCTYLSULFONAMIDO)CYCLOPENTYL]ACETIC ACID; 2 HYDROXY 3 (OCTYLSULFONAMIDO)CYCLOHEXANECARBOXYLIC ACID; 2 HYDROXY 3 (OCTYLSULFONAMIDO)CYCLOPENTANECARBOXYLIC ACID; 3 HYDROXY 2 (OCTYLSULFONAMIDO)CYCLOPENTANECARBOXYLIC ACID; ACYLTRANSFERASE INHIBITOR; BENZOIC ACID DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; GLYCEROL 3 PHOSPHATE ACYLTRANSFERASE; PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHLOROPLAST; COMPUTER MODEL; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IN VITRO STUDY; MOLECULAR DOCKING; SQUASH; STEREOCHEMISTRY;

DRUG DESIGN; ENZYME INHIBITORS; GLYCEROL-3-PHOSPHATE O-ACYLTRANSFERASE; HUMANS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OBESITY; STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA;

EID: 77955981959     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.06.091     Document Type: Article

References (26)

1. R.A. Coleman, T.M. Lewin, and D.M. Muoio Annu. Rev. Nutr. 18 1998 331
2. R.A. Coleman, and D.P. Lee Prog. Lipid Res. 43 2004 134
3. P. Cullen Biochem. Soc. Trans. 31 2003 1080
4. The Expert Panel. Arch. Intern. Med. 1986, 148, 36.
5. T.M. Lewin, N.M.J. Schwerbrock, D.P. Lee, and R.A. Coleman J. Biol. Chem. 279 2004 13488
6. C.A. Nagle, L. Vergnes, H. Dejong, S. Wang, T.M. Lewin, K. Reue, and R.A. Coleman J. Lipid Res. 49 2008 823
7. G. Monroy, F.H. Rola, and M.E. Pullman J. Biol. Chem. 247 1972 6884
8. L.E. Hammond, P.A. Gallagher, S. Wang, S. Hiller, K.D. Kluckman, E.L. Posey-Marcos, N. Maeda, and R.A. Coleman Mol. Cell Bio. 22 2004 8204
9. D. Lindén, L. William-Olsson, M. Rhedin, A.-K. Asztély, J.C. Clapham, and S. Schreyer J. Lipid Res. 45 2004 1279
10. D. Lindén, L. William-Olsson, A. Ahnmark, K. Ekroos, C. Hallberg, H.P. Sjögren, B. Becker, L. Svensson, J.C. Clapham, J. Oscarsson, and S. Schreyer FASEB 20 2006 434
11. F.R. Van der Leij, A.M. Kram, B. Bartelds, H. Roelofsen, G.B. Smid, J. Takens, V.A. Zammit, and J.R.G. Kuipers Biochem. J. 341 1999 777
12. D.G. Hardie, J. Corton, Y.P. Ching, S.P. Davies, and S. Hawley Biochem. Soc. Trans. 25 1997 1229
13. D.M. Muoio, K. Seefeld, L.A. Witters, and R.A. Coleman Biochem. J. 338 1999 783
14. L.E. Hammond, S. Neschen, A.J. Romanelli, G.W. Cline, O.R. Ilkayeva, G.I. Shulman, D.M. Muoio, and R.A. Coleman J. Biol. Chem. 280 2005 25629
15. A.P. Turnbull, J.B. Rafferty, S.E. Sedelnikova, A.R. Slabas, T.P. Schierer, J.T.M. Kroon, J.W. Simon, T. Fawcett, I. Nishida, N. Murata, and D.W. Rice Structure 9 2001 347
16. E.A. Wydysh, S.M. Medghalchi, A. Vadlamudi, and C.A. Townsend J. Med. Chem. 52 2009 3317
17. J.D. Weissman, A.J. Hancock, R. MacQuarrie, I.S. Lee-Abraham, and H.Z. Sable J. Biol. Chem. 257 1982 3618
18. T.L. Hutchison, A. Saeed, P.E. Wolkowicz, J.B. McMillin, and W.J. Brouillette Bioorg. Med. Chem. 7 1999 1505
19. C. Ollivier, and P. Renaud J. Am. Chem. Soc. 123 2001 4717
20. F. Zhang, Z.J. Song, D. Tschaen, and R.P. Volante Org. Lett. 6 2004 3775
21. D.M. Bartley, and J.K. Coward J. Org. Chem. 70 2005 6757
22. D. Buisson, and R. Azerad Tetrahedron Lett. 27 1986 2631
23. W.J. Brouillette, A. Saeed, A. Abuelyaman, T.L. Hutchison, P.E. Wolkowicz, and J.B. McMillin J. Org. Chem. 59 1994 4297
24. C.K. Chung, K. Kim, Y.H. Rhee, and H. Lee Bull. Kor. Chem. Soc. 20 1999 99
25. A.J. Pearson, and S.Y. Hsu J. Org. Chem. 51 1986 2505
26. D.M. Schlossman, and R.M. Bell J. Biol. Chem. 251 1976 5738