Resolution, molecular structure and biological activities of the D- and L-enantiomers of potent anti-implantation agent, DL-2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 9, 1999, Pages 2083-2090

  Hajela, K ^a   Pandey, Jaya ^a   Dwivedy, A ^a   Dhar, J D ^a   Sarkhel, Sanjay ^a   Maulik, P R ^a   Velumurugan, D ^b  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b UNIVERSITY OF MADRAS   (India)

Author keywords

Anti estrogen; Anti implantation; Configuration; Enantiomers

Indexed keywords

2 [4 (2 PIPERIDINOETHOXY)PHENYL] 3 PHENYL 2H 1 BENZOPYRAN; ANTIESTROGEN; CENTCHROMAN; ESTRADIOL; NAFOXIDINE; RALOXIFENE; TAMOXIFEN; TRIOXIFENE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTRACEPTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG EFFICACY; DRUG STRUCTURE; ENANTIOMER; FEMALE; NONHUMAN; RAT; RECEPTOR AFFINITY; STEREOCHEMISTRY; UTERUS WEIGHT; X RAY CRYSTALLOGRAPHY;

ANIMALS; BENZOPYRANS; EMBRYO IMPLANTATION; ESTROGEN ANTAGONISTS; FEMALE; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERIDINES; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, ESTROGEN; STEREOISOMERISM; UTERUS;

EID: 0032881253     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00131-5     Document Type: Article

References (31)

1. Harper M.J.K., Walpole A.L. J. Reprod. Fertil. 13:1967;101-119.
2. Lednicer D., Lyster S.C., Duncan G.W. J. Med. Chem. 10:1967;78-84.
3. Salman M., Ray S., Anand Nitya, Agarwal A.K., Singh M.M., Setty B.S., Kamboj V.P. J. Med. Chem. 29:1986;1801-1803.
4. Jordan V.C., Haldeman B., Allen K.E. Endocrinology. 108:1981;1353-1361.
5. Robertson D.W., Katzenellenbogen J.A., Long D.J., Rorke E.A., Katzenellenbogen B.S. J. Steroid Biochem. 16:1982;1-13.
6. Robertson D.W., Katzenellenbogen J.A., Hayes J.R., Katzenellenbogen B.S. J. Med. Chem. 25:1982;167-171.
7. Iyer R.N., Gopalchari R. Indian J. Pharmacy. 31:1969;49-54.
8. Gopalchari R., Iyer R.N., Kamboj V.P., Kar A.B. Contraception. 2:1970;199-205.
9. Black L.J., Goode R.L. Life Sciences. 26:1980;1453-1458.
10. Mittal S., Durani S., Kapil R.S. J. Med. Chem. 28:1985;492-497.
11. Delmas P.D., Bjarnason N.N., Mitlak B.H., Ravoux A.C., Shah A.S., Huster W.J., Doper M., Christiansen C. N. Engl. J. Med. 337:1997;1641.
12. Grese T.A., Sluka J.P., Bryant H.U., Cullinan G.J., Glasebrook A.L., Jones C.D., Matsumoto K., Palkowitz A.D., Sato M., Termine J.D., Winter M.A., Yang N.N., Dodge J.A. Proc. Natl. Acad. Sci. USA. 94:1997;14105-14110.
13. Saeed A., Sharma A.P., Durani N., Jain R., Durani S., Kapil R.S. J. Med. Chem. 33:1990;3210. 3216, 3222.
14. Durani S., Anand Nitya Internat. J. Quantum Chem. 20:1981;71-83.
15. Dhar J.D., Setty B.S., Durani S., Kapil R.S. Contraception. 44:1991;461-472.
16. Sreenivasulu S., Singh M.M., Setty B.S., Kamboj V.P. Contraception. 48:1993;597-609.
17. Hajela K., Kapoor K.K., Kapil R.S. Bioorg. Med. Chem. 3:1995;1417-1421.
18. Hajela K., Kapil R.S. Eur. J. Med. Chem. 32:1997;135-142.
19. Johnson, C. K. ORTEP ORNI-3794; Oak Ridge National Laboratory: Oak Ridge (TN), 1965.
20. Rosati R.L., Jardine P.D.S., Cameron K.O., Thompson D.D., Ke H.H., Toler S.M., Brown T.A., Pan L.C., Ebbinghans C.F., Reinhold A.R., Elliott N.C., Newhouse B.N., Christina M.T., Sweetnam P.M., Cole M.J., Arriola M.W., Ganthier J.W., Crawford D.T., Nikerson D.F., Pirie C.M., Qi H., Simmons H.A., Tkalcevic G.T. J. Med. Chem. 41:1998;2928-2931.
21. Ray S., Tandon A., Dwivedy I., Wilson S.R., O'Neil J.P., Katzenellenbogen J.A. J. Med. Chem. 37:1994;696-700.
22. Brzozowski A.M., Pike A.C.W., Dautor Z., Hubbard R.E., Monn T., Engstrom O., Ohman L., Greene G.L., Gustafsson J.A., Carlquist M. Nature. 389:1997;753-757.
23. Kym P.R., Anstead G.M., Pinney K.G., Wilson S.R., Katzenellenbogen J.A. J. Med. Chem. 36:1993;3910-3922.
24. Gauthier S., Caron B., Cloutier J., Dory Y.L., Favre A., Laronche D., Mailhot J., Quellet C., Schwerdtfeger A., Leblane G., Martel C., Sinard J., Merand Y., Belonger A., Labrie C., Labrie F. J. Med. Chem. 40:1997;2117-2122.
25. Anstead G., Carlson K.E., Katzenellenbogen J.A. Steroids. 62:1997;268-303.
26. Saeed, A.; Ph.D. dissertation, 1987.
27. Dhar J.D., Dwiedi A., Srivastava A., Setty B.B. Contraception. 49:1994;609-616.
28. Grese T.A., Pennington L.D., Sluka J.P., Adrian M.D., Cole H.W., Fuson T.R., Magree D.E., Phillips D.L., Rowley E.R., Shetler P.K., Short L.L., Venugopalan M., Yang N.N., Sato M., Glasebrook A.L., Bryant H.U. J. Med. Chem. 41:1998;1272-1283.
29. Wilson, A. J. C., Ed. Dordrecht, Kuwer Academic, International Tables for X-ray Crystallography; Kluwer Academic: Dordrecht (The Netherlands), 1992; Vol. C, pp. 219-502.
30. Sheldrick G.M. Acta Crystallogr. Sect. A. 46:1990;467-473.
31. Sheldrick, G. M. SHELXL-93 Program for Crystal Structure Refinement; Gottingen (Germany), 1993.