Unique structure-activity relationship for 4-isoxazolyl-1,4-dihydropyridines

Journal of Medicinal Chemistry

Volumn 46, Issue 1, 2003, Pages 87-96

  Zamponi, Gerald W ^a   Stotz, Stephanie C ^a   Staples, Richard J ^b   Andro, Tina M ^c   Nelson, Jared K ^c   Hulubei, Victoria ^c   Blumenfeld, Alex ^c   Natale, Nicholas R ^c  

^a UNIVERSITY OF CALGARY   (Canada)

^b HARVARD UNIVERSITY   (United States)

^c UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; ISOXAZOLE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CALCULATION; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PATCH CLAMP; SOLID STATE; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

CALCIUM CHANNELS; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DIHYDROPYRIDINES; HUMANS; ISOXAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PATCH-CLAMP TECHNIQUES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037413531     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020354w     Document Type: Article

References (26)

1. (a) Zamponi, G. W. Antagonist sites of voltage-dependent channels. Drug. Dev. Res. 1997, 42, 131-143.
2. (b) Striessnig, J. Pharmacology, Structure and function of cardiac L-type calcium channels. Cell Physiol. Biochem. 1999, 9, 242-269.
3. 2+ channel ligands: Structure-function relationships of the 1,4-dihydropyridines. Med. Res. Rev. 1989, 9, 123-180.
4. (d) Natale, N. R. Learning from the Hantzsch synthesis. In Chemical Innovation; American Chemical Society: Washington, DC, 2001.
5. (a) New Analyses Regarding the Safety of Calcium-Channel Blockers: A Statement for Health Professionals from the National Heart, Lung, and Blood Institute, September 1, 1995. 〉http://www.nhlbi.nih.gov/new/press/cutlrccb.txt〈.
6. (b) Psaty, B. M.; Heckbert, S.; Koepsell, T.; Siscovick, D. S.; Raghunathan, T. E.; Weiss, N. S.; Rosendal, F. R.; Lemaitre, R. N.; Smith, N. L.; Wahl, P. W.; Wagner, E. H.; Furberg, C. D. The risk of myocardial infarction associated with antihypertensive drug therapy. J. Am. Med. Assoc. 1995, 274, 620-625.
7. (c) Pahor, M.; Guralnik, J. M.; Ferruci, L.; Corti, M. C.; Salive, M. E.; Cerhan, J. R.; Wallace, R. B.; Havlik, R. J. Calcium channel blockade and incidence of cancer in aged populations. Lancet 1996, 348, 493-497.
8. (d) Fitzpatrick, A. L.; Daling, J. R.; Furberg, C. D.; Kronmal, R. A.; Weissfeld, J. L. Use of calcium channel blockers and breast carcinoma risk in postmenopausal women. Cancer 1997, 80, 1438-1447.
9. Joint National Committee. The sixth report of the Joint National Committee on prevention, detection, evaluation, and treatment of high blood pressure (JNC-VI). Arch. Intern. Med. 1997, 157, 2413-2446.
10. Doyle, D. A.; Cabral, J. M.; Pfuetner, R. A.; Kuo, A.; Gulbis, J. M.; Cohen, S. L.; Chait, B. T.; MacKinnon, R. The structure of the potassium channel: Molecular basis of K+ conduction and selectivity. Science 1998, 280, 69-77.
11. Peterson, B. Z.; Tanada, T. N.; Catterall, W. A. Molecular determinants of high affinity binding in L-type calcium channels. J. Biol. Chem. 1996, 271, 5293-5296.
12. 2+ channel. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14906-14911.
13. Natale, N. R.; Rogers, M. E.; Staples, R. J.; Triggle, D. J.; Rutledge, A. Lipophilic 4-isoxazolyl-1,4-dihydropyridines: Synthesis and structure-activity relationships. J. Med. Chem. 1999, 42, 3087-3093.
14. Schleifer, K.-J. Stereoselective characterization of the 1,4-dihydropyridine binding site at L-type calcium channels in the resting state and the opened/inactivated state. J. Med. Chem. 1999, 42, 2204-2211.
15. 1E calcium channels. J. Biol. Chem. 1999, 274, 22428-22436.
16. Natale, N. R.; Triggle, D. J.; Palmer, R. B.; Lefler, B. J.; Edwards, W. D. 4-Isoxazolyl-1,4-dihydropyridines: Biological, theoretical, and structural studies. J. Med. Chem. 1990, 33, 2255-2259.
17. Palmer, R. B.; Andro, T. M.; Natale, N. R.; Anderson, N. H. Conformational preferences and dynamics of 4-isoxazolyl-1,4-dihydropyridine calcium channel antagonists as determined by variable temperature NMR and NOE experiments. Magn. Reson. Chem. 1996, 34, 495-504.
18. McKenna, J. I.; Schlicksupp, L.; Natale, N. R.; Willett, R. D.; Maryanoff, B. E.; Flaim, S. F. Cardioactivity and solid-state structure of two 4-isoxazolyldihydropyridines related to the 4-aryldihydropyridine calcium-channel blockers. J. Med. Chem. 1988, 31, 473-476.
19. 2+ antagonist binding properties and putative folding structure of a recombinant high affinity dihydropyridine binding domain. Biochem. J. 2000, 347, 829-826.
20. Liu, K.; Shelton, B. R.; Howe, R. K. A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors). J. Org. Chem. 1980, 45, 3916-3918.
21. Doyle, F. P.; Hanson, J. C.; Long, A. A.; Nayler, J. H. C.; Stove, E. R. Derivatives of 6-aminopenicillanic acid. Part IV. Penicillins from 3- and 5-phenylisoxazole-4-carboxylic acids and their alkyl and halogen derivatives. J. Chem. Soc. 1963, 5838-5845.
22. Heck, R.; Oflenloch, R.; Wolf, R. Eine verbesserte methode zur synthese substituierter isoxazol-4-carbaldehyde. Synthesis 1990, 62-64.
23. Claridge, T. D. High Resolution NMR Techniques in Organic Chemistry; Pergamon: New York, 1999.
24. Snutch, T. P.; Tomlinson, W. J.; Leonard, J. P.; Gilbert, M. M. Distinct calcium channels are generated by alternative splicing and are differentially expressed in the mammalian CNS. Neuron 1991, 7, 45-57.
25. (a) Oki, M. The Chemistry of Rotational Isomers; Springer: New York, 1993.
26. (b) Oki, M. Recent advances in atropisomerism. Top. Stereochem. 1983, 14, 1. Ôki's definition for atropisomers suggests 22.3 kcal/mol at 300 K and 26.2 kcal/mol at 350 K as values where the isomers exist as isolable entities.