Cyclopentane-1,3-dione: A novel isostere for the carboxylic acid functional group. Application to the design of potent thromboxane (A2) receptor antagonists

Journal of Medicinal Chemistry

Volumn 54, Issue 19, 2011, Pages 6969-6983

  Ballatore, Carlo ^a   Soper, James H ^a   Piscitelli, Francesco ^a   James, Michael ^a   Huang, Longchuan ^a   Atasoylu, Onur ^a   Huryn, Donna M ^a   Trojanowski, John Q ^a   Lee, Virginia M Y ^a   Brunden, Kurt R ^a   Smith, Amos B ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 (2 (4 CHLOROPHENYLSULFONAMIDO)ETHYL)PHENYL)PROPANOIC ACID; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTANE 1,3 DIONE; CYCLOPENTANE DERIVATIVE; TETRAZOLE DERIVATIVE; THROMBOXANE A2 RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; ASSAY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; LIPOPHILICITY; PHYSICAL CHEMISTRY; RADIOLIGAND BINDING ASSAY; SUBSTITUTION REACTION;

ANIMALS; CARBOXYLIC ACIDS; CYCLOPENTANES; DRUG DESIGN; HEK293 CELLS; HUMANS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; QUANTUM THEORY; RADIOLIGAND ASSAY; RECEPTORS, THROMBOXANE A2, PROSTAGLANDIN H2; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLES;

EID: 80053922655     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200980u     Document Type: Article

References (23)

1. Patani, G. A.; LaVoie, E. J. Bioisosterism: a rational approach in drug design Chem. Rev. 1996, 96, 3147-3176 (Pubitemid 126641132)
2. Meanwell, N. A. Synopsis of some recent tactical application of bioisosteres in drug design J. Med. Chem. 2011, 54, 2529-2591
3. Herr, R. J. 5-Substituted-1 H -tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods Bioorg. Med. Chem. 2002, 10, 3379-3393
4. Boothe, J.; Wilkinson, R.; Kushner, S.; Williams, J. Synthesis of aureomycin degradation products. II J. Am. Chem. Soc. 1953, 75, 1732-1733
5. Hiraga, K. Structures of cyclopentanepolyones Chem. Pharm. Bull. (Tokyo) 1965, 13, 1300
6. Katrusiak, A. Structure of 1, 3-cyclopentanedione Acta Crystallogr., C 1990, 46, 1289-1293
7. Katrusiak, A. Structure of 2-methyl-1, 3-cyclopentanedione Acta Crystallogr., C 1989, 45, 1897-1899
8. Dickinson, R. P.; Dack, K. N.; Long, C. J.; Steele, J. Thromboxane modulating agents. 3. 1 H -Imidazol-1-ylalkyl- and 3-pyridinylalkyl-substituted 3-[2-[(arylsulfonyl)amino]ethyl]benzenepropanoic acid derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists J. Med. Chem. 1997, 40, 3442-3452
9. Koreeda, M.; Liang, Y.; Akagi, H. Easy generation of the dianions of 3-isobutoxycyclopent-2-en-1-ones and their reactions J. Chem. Soc., Chem. Commun. 1979, 449-450
10. Ramachary, D. B.; Kishor, M. Direct amino acid-catalyzed cascade biomimetic reductive alkylations: application to the asymmetric synthesis of Hajos-Parrish ketone analogues Org. Biomol. Chem. 2008, 6, 4176-4187
11. Tilley, J. W.; Danho, W.; Lovey, K.; Wagner, R.; Swistok, J.; Makofske, R.; Michalewsky, J.; Triscari, J.; Nelson, D.; Weatherford, S. Carboxylic acids and tetrazoles as isosteric replacements for sulfate in cholecystokinin analogs J. Med. Chem. 1991, 34, 1125-1136
12. Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Davis Harris, G.; Weinreb, S. M. Mitsunobu reactions of N -alkyl and N -acyl sulfonamides-an efficient route to protected amines Tetrahedron Lett. 1989, 30, 5709-5712
13. Peters, L.; Frohlich, R.; Boyd, A. S. F.; Kraft, A. Noncovalent interactions between tetrazole and an N, N ′-diethyl-substituted benzamidine J. Org. Chem. 2001, 66, 3291-3298 (Pubitemid 32878935)
14. Tominey, A. F.; Docherty, P. H.; Rosair, G. M.; Quenardelle, R.; Kraft, A. Unusually weak binding interactions in tetrazole-amidine complexes Org. Lett. 2006, 8, 1279-1282 (Pubitemid 43587420)
15. Job, P. Formation and stability of inorganic complexes in solution Ann. Chim. 1925, 9, 113-125
16. Shenker, A.; Goldsmith, P.; Unson, C. G.; Spiegel, A. M. The G protein coupled to the thromboxane A2 receptor in human platelets is a member of the novel Gq family J. Biol. Chem. 1991, 266, 9309-9313 (Pubitemid 21906653)
17. Bylund, D.; Toews, M. Radioligand binding methods for membrane preparations and intact cells Methods Mol. Biol. (Clifton, NJ) 2011, 746, 135
18. Ruan, K. H.; Wu, J.; So, S. P.; Jenkins, L. A.; Ruan, C. H. NMR structure of the thromboxane A2 receptor ligand recognition pocket Eur. J. Biochem. 2004, 271, 3006-3016 (Pubitemid 38980285)
19. Hirata, M.; Hayashi, Y.; Ushikubi, F.; Yokota, Y.; Kageyama, R.; Nakanishi, S.; Narumiya, S. Cloning and expression of cDNA for a human thromboxane A2 receptor Nature 1991, 349, 617-620 (Pubitemid 21912117)
20. Yamamoto, Y.; Kamiya, K.; Terao, S. Modeling of human thromboxane A2 receptor and analysis of the receptor-ligand interaction J. Med. Chem. 1993, 36, 820-825 (Pubitemid 23118774)
21. Dogne, J.; Hanson, J.; Leval, X.; Pratico, D.; Pace-Asciak, C.; Drion, P.; Pirotte, B.; Ruan, K. From the design to the clinical application of thromboxane modulators Curr. Pharm. Des. 2006, 12, 903-923
22. Shineman, D. W.; Zhang, B.; Leight, S. N.; Pratico, D.; Lee, V. M. Y. Thromboxane receptor activation mediates isoprostane-induced increases in amyloid pathology in Tg2576 mice J. Neurosci. 2008, 28, 4785-4794
23. Yung-Chi, C.; Prusoff, W. H. Relationship between the inhibition constant (KI) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction Biochem. Pharmacol. 1973, 22, 3099-3108