Synthesis and estrogen receptor binding of (17α,20E)-and (17α,20Z)-21-phenylthio-and 21-phenylseleno-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols

Steroids

Volumn 61, Issue 6, 1996, Pages 384-389

  Napolitano, Elio ^a   Fiaschi, Rita ^b   Herman, Lee W ^c   Hanson, Robert N ^c  

^a UNIVERSITY OF PISA   (Italy)

^b SCUOLA NORMALE SUPERIORE   (Italy)

^c NORTHEASTERN UNIVERSITY   (United States)

Author keywords

Molecular modeling; Steroidal der vatives; Thio(seleno)vinyl analogs

Indexed keywords

ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR;

ARTICLE; BINDING COMPETITION; HORMONE RECEPTOR INTERACTION; HORMONE SYNTHESIS; MOLECULAR MODEL; NONHUMAN; RAT; RECEPTOR AFFINITY; RECEPTOR BINDING;

ANIMALS; BINDING SITES; BINDING, COMPETITIVE; ESTRADIOL; FEMALE; MODELS, MOLECULAR; RATS; RECEPTORS, ESTROGEN; STRUCTURE-ACTIVITY RELATIONSHIP; UTERUS;

EID: 0029891668     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0039-128X(96)00045-1     Document Type: Article

References (25)

1. Korenman SG (1969). Competitive binding affinity of estrogens and its relation to estrogcnic potency. Steroids 13:163-177.
2. Counsell RE, Klimstra PD, Elton RL, Nutting EE (1968). Chemical and biological properties of some 17-substituted estradiol derivatives. J Med Chem 9:689-692.
3. Raynaud J-P, Ojasoo T (1986). The design and use of sex steroid antagonists. J Steroid Biochem 25:811-833.
4. Raynaud J-P, Ojasoo T (1986). Receptor binding as a tool in the development of selective new bioactive steroids and nonsteroids. In: Harms AF (ed), Innovative Approach in Drug Research. Elsevier Science Publications, Amsterdam, pp. 47-72.
5. Raynaud J-P, Ojasoo T, Bouton MM, Philibert D (1979). Receptor binding as a tool in the development of new bioactive steroids. In: Ariens EJ (ed), Drug Design, Vol. 8, Academic Press, New York, pp. 169-214.
6. Salman M, Reddy BR, Ray S, Stotter PL, Chamness GC (1988). 17α-Allyl estradiol analogues as candidates for development of high affinity fluorescein-estradiol conjugates. J Steroid Biochem 24:539-548.
7. Sadek SA, Shaw SM, Kessler WV, Wolf GC (1981). Selenosteroids as potential estrogen-receptor scanning agents. J Org Chem 46: 3259-3262.
8. Sadek SA, Kessler WV, Shaw SM, Anderson JN, Wolf GC (1982). Selenium labeling in nuclear medicine. 2. D ring substituted estrogens. J Med Chem 25:1488-1492.
9. Arunachalam T, Caspi E (1981). Synthesis of selenoestrogens. J Org Chem 46:3415-3420.
10. Longcope C, Arunachalam T, Caspi E (1982). The biologic activity of selenoestrogens. Can J Biochem 60:152-156.
11. Fevig TL, Katzenellenbogen JA (1987). A short, stereoselective route to 16α-(substituted alkyl) estradiol derivatives. J Org Chem 52:247-251.
12. Fevig TL, Mao MK, Katzenellenbogen JA (1988). Estrogen receptor binding tolerance to 16α-substituted estradiol derivatives. Steroids 51:471-497.
13. Napolitano E, Fiaschi R, Hanson RN (1991). Structure-activity relationships of estrogenic ligands: synthesis and evaluation of (17α-, 20E) and (17α,20Z)-halogenated-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols. J Med Chem 34:2754-2759.
14. Hoyte RM, Rosner W, Johnson IS, Zielinski J, Hochberg RB (1985). Synthesis and evaluation of potential radioligands for the progesterone receptor. J Med Chem 28:1695-1699.
15. Hofmeister H, Laurent H, Schulze PE, Weichert R (1986). Synthesis of 17α-bromovinyl and 17α-iodovinylnortestesterone derivatives. Tetrahedron 42:3575-3578.
16. Belanger A, Philibert D. Teutsch G (1981). Regio and stereospecific synthesis of 11β-substituted 19-norsteroids. Steroids 37:361-382.
17. Neef G, Beier S, Elger W, Henderson D, Weichert R (1984). New steroids with anti-progestational and antiglucocorticoid activities. Steroids 44:349-372.
18. Philibert D, Hardy M, Gaillard-Moguilewsky M, Nique F, Tournemine C, Nedelec L (1989). New analogs of mifepristone with more dissociated antiprogesterone activities. J Steroid Biochem 34: 413-417.
19. Evans RM (1988). The steroid and thyroid hormone receptor superfamily. Science 240:889-895.
20. O'Mally BL (1990). The steroid receptor superfamily: more excitement predicted for the future. Mol Endrocinol 4:363-369.
21. Carson-Jurica MA, Schrader WT, O'Mally BC (1990), Steroid receptor family: structure and functions. Endocr Rev 11:201-220.
22. Katzenellenbogen JA, Johnson JH, Jr., Myers HM (1973). Reagents for photoaffinity labeling of estrogen binding protein. The binding affinity of some azide and diazo derivatives of estradiol, estrone and hexestrol for the estrogen binding protein of rat uterus. Biochemistry 12:4085-4092.
23. Katzenellenbogen JA, Carlson KE, Johnson JH, Jr., Myers HM (1977). Estrogen photoaffinity labels. II. Reversible binding and covalent attachment of photosensitive hexestrol derivatives to the uterine estrogen receptor. Biochemistry 16:1970-1976.
24. Allinger NL, Allinger JA, Yan LQ (1989). Molecular mechanisms (MM2) calculations on organoselenium and tellurium compounds. J Mol Struct 210:363-369.
25. 13C nuclear magnetic resonance study of 17α-substituted estradiols. Steroids 60:830-836.