Evaluation of the cyclopentane-1,2-dione as a potential bio-isostere of the carboxylic acid functional group

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 17, 2014, Pages 4171-4175

  Ballatore, Carlo ^a,b   Gay, Bryant ^a   Huang, Longchuan ^a   Robinson, Katie Herbst ^b   James, Michael J ^b   Trojanowski, John Q ^b   Lee, Virginia M Y ^b   Brunden, Kurt R ^b   Smith, Amos B ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Carboxylic acid bio isosteres; Cyclopentane 1,2 dione

Indexed keywords

3 [3 [2 [(4 CHLOROPHENYL)SULFONAMIDO]ETHYL]PHENYL]PROPANOIC ACID; CARBOXYLIC ACID; CYCLOPENTANE 1,2 DIONE; CYCLOPENTANE DERIVATIVE; FUNCTIONAL GROUP; THROMBOXANE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; 4-CHLORO-N-(3-((2-HYDROXY-3-OXOCYCLOPENT-1-EN-1-YL)METHYL)PHENETHYL)BENZENESULFONAMIDE; SULFONAMIDE; THROMBOXANE A2 RECEPTOR;

ACIDITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DRUG SCREENING; DRUG SYNTHESIS; GEOMETRY; HYDROGEN BOND; IC 50; TAUTOMER; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DOSE RESPONSE; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CARBOXYLIC ACIDS; CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, THROMBOXANE A2, PROSTAGLANDIN H2; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84906939078     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.07.047     Document Type: Article

References (16)

1. P.J. Hajduk, M. Bures, J. Praestgaard, and S.W. Fesik J. Med. Chem. 43 2000 3443
2. C. Ballatore, D.M. Huryn, and A.B. Smith III ChemMedChem 8 2013 385
3. W.A. Kinney, M. Abou-Gharbia, D.T. Garrison, J. Schmid, D.M. Kowal, D.R. Bramlett, T.L. Miller, R.P. Tasse, M.M. Zaleska, and J.A. Moyer J. Med. Chem. 41 1998 236
4. E.F. Campbell, A.K. Park, W.A. Kinney, R.W. Fengl, and L.S. Liebeskind J. Org. Chem. 60 1995 1470
5. R.M. Soll, W.A. Kinney, J. Primeau, L. Garrick, R.J. McCaully, T. Colatsky, G. Oshiro, C.H. Park, D. Hartupee, V. White, J. McCallum, A. Russo, J. Dinish, and A. Wojdan Bioorg. Med. Chem. Lett. 3 1993 757
6. W.A. Kinney, N.E. Lee, D.T. Garrison, E.J. Podlesny, J.T. Simmonds, D. Bramlett, R.R. Notvest, D.M. Kowal, and R.P. Tasse J. Med. Chem. 35 1992 4720
7. R.P. Dickinson, K.N. Dack, C.J. Long, and J. Steele J. Med. Chem. 40 1997 3442
8. C. Ballatore, J.H. Soper, F. Piscitelli, M. James, L. Huang, O. Atasoylu, D.M. Huryn, J.Q. Trojanowski, V.M. Lee, K.R. Brunden, and A.B. Smith III J. Med. Chem. 54 2011 6969
9. G. Schwarzenbach, and C. Wittwer Helv. Chem. Acta 30 1947 663
10. K. Hiraga Chem. Pharm. Bull. (Tokyo) 13 1965 1300
11. P. Vittorelli, H. Heimgartner, H. Schmid, P. Hoet, and L. Ghosez Tetrahedron 30 1974 3737
12. B.M. Trost, G. Dong, and J.A. Vance Chemistry 16 2010 6265
13. H. Muxfeldt, M. Weigele, and V.V. Rheenen J. Org. Chem. 30 1965 3573
14. E. Aqad, P. Leriche, G. Mabon, A. Gorgues, M. Allain, A. Riou, A. Ellern, and V. Khodorkovsky Tetrahedron 59 2003 5773
15. A. Jõgi, M. Ilves, A. Paju, T. Pehk, T. Kailas, A.-M. Müürisepp, and M. Lopp Tetrahedron: Asymmetry 19 2008 628
16. B. Cimetiere, T. Dubuffet, O. Muller, J.J. Descombes, S. Simonet, M. Laubie, T.J. Verbeuren, and G. Lavielle Bioorg. Med. Chem. Lett. 8 1998 1375