Design and synthesis of haptens for application to the preparation of chiral 1,4-dihydropyridines

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 3, 1998, Pages 518-522

  Ikeda, Kiyoshi ^a   Kato, Tatsuhisa ^a   Suzuki, Takehisa ^a   Achiwa, Kazuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

1,4 Dihydropyridine; Catalytic antibody; Hapten; Hydrolysis; Transition state analog

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; 6 [HYDROXY [5 (METHOXYCARBONYL) 2,6 DIMETHYL 4 (3 NITROPHENYL)(1,4 DIHYDRO PYRIDINYL)PHOSPHORYL]OXY]HEXANOIC ACID; CARBOXYLIC ACID; CATALYTIC ANTIBODY; ESTER; HAPTEN; PHOSPHONIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; HYDROLYSIS; OPTICAL ROTATION; SYNTHESIS;

EID: 0031968808     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.518     Document Type: Article

References (19)

1. a) Loev B., Tedeshi R. E., U.S. Patent 3511847 (1970), Smith Kline and French;
2. b) Loev B., Ehrreich S. J., Tedeshi R. E., J. Pharm. Pharmacol., 24, 917-918 (1972).
3. Loev B., Goodman M. M., Snader K. M., Tedeshi R. E., Macko E., J. Med. Chem., 17, 956-965 (1974).
4. a) Bessert F., Vater W., Naturwissenschaften, 58, 578 (1971);
5. b) Ohtsuka M., Yokota M., Kodama I., Yamada K., Shibata S., Gen. Pharmacol., 20, 539-556 (1989);
6. c) Freedmann D. D., Waters D. D., Drugs, 34, 578-598 (1978).
7. a) Ebiike H., Terao Y., Achiwa K., Tetrahedron Lett., 32, 5805-5808 (1991);
8. b) Ebiike H., Maruyama K., Yamazaki Y., Hirose Y., Kariya K., Sasaki I., Kurono Y., Terao Y., Achiwa K., Chem. Pharm. Bull., 45, 863-868 (1997).
9. a) Janda K. D., Benkovic S. J., Lerner R. A., Science, 244, 437-440 (1989);
10. b) Schultz P. G., Lerner R. A., Acc. Chem. Res., 26, 391-395 (1993);
11. Lerner R. A., Benkovic S. J., Schultz P. G., Science, 252, 659-667 (1991);
12. Ikeda S., Weinhouse M.I., Janda K. D., Lerner R. A., J. Am. Chem. Soc., 113, 7763-7764 (1991);
13. e) Fujii I., Lerner R. A., Janda K. D., ibid., 113, 8528-8529 (1991);
14. f) Miyashita H., Karaki Y., Kikuchi M., Fujii I., Proc. Natl. Acad. Sci. U.S.A., 90, 5337-5340 (1993);
15. g) Iwabuchi Y., Miyashita H., Tanimura R., Kinoshita K., Kikuchi M., Fujii I., J. Am. Chem. Soc., 116, 771-772 (1994);
16. h] Basmadjan G. P., Singh S., Sastrodjojo B., Smith B. T., Avor K. S., Chang F., Mills S. L., Scale T. W., Chem. Pharm. Bull., 43, 1902-1911 (1995);
17. Tanaka F., Kinoshita K., Tanimura R., Fujii T., J. Am. Chem. Soc., 118, 2332-2339 (1996).
18. Ikeda K., Achiwa K., Bioorg. Med. Chem. Lett., 7, 225-228 (1997).
19. Tijssen P., "Practice and Theory of Enzyme Immunology," ed. by Burdon R. H., van Knippenberg P. H., Elsevier, New York, 1987, pp. 39-41.