11β-aryl steroids in the androstene series. The role of the 11β-region in steroid progesterone receptor interaction

Tetrahedron

Volumn 52, Issue 5, 1996, Pages 1529-1542

  Cleve, Arwed ^a   Fritzemeier, Karl Heinrich ^a   Heinrich, Nikolaus ^a   Klar, Ulrich ^a   Müller Fahrnow, Anke ^a   Neef, Günter ^a   Ottow, Eckhard ^a   Schwede, Wolfgang ^a  

^a BAYER PHARMA AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

11BETA (4 DIMETHYLAMINOPHENYL) 17BETA HYDROXY 9,19 CYCLIC 9BETA ANDROST 4 EN 3 ONE; 17BETA HYDROXY 11BETA (4 METHOXYPHENYL)ANDROST 4 EN 3 ONE; ANDROGEN; PROGESTERONE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; RABBIT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; UTERUS; X RAY ANALYSIS;

EID: 0030064337     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00983-3     Document Type: Article

References (18)

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6. The phenyl torsions of the minimum structures have been calculated to be 27° for the 10β-H compound ZK 135 660 and 21° for RU 38 486, respectively.
7. Neef, G.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1983, 24, 5205-5208; Schering AG (Cleve, A.; Scheidges, C.; Neef, G.; Ottow, E.; Elger, W.; Beier, S.; Inv.) Eur. Pat. Appl. EP 404,283 (27.12.1990) [Chem. Abstr. 1991, 114, P 164625f].
8. Neef, G.; Sauer, G.; Wiechert, R. Tetrahedron Lett. 1983, 24, 5205-5208; Schering AG (Cleve, A.; Scheidges, C.; Neef, G.; Ottow, E.; Elger, W.; Beier, S.; Inv.) Eur. Pat. Appl. EP 404,283 (27.12.1990) [Chem. Abstr. 1991, 114, P 164625f].
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10. The following products were characterized (see Experimental Section): (equation presented) (equation presented) Using alcohol free conditions, e.g. dil. NaOH/THF, increased the relative amounts of 27 and 28.
11. Cleve, A. unpublished results.
12. For a review on triflate/nonaflate reactions, see: Ritter, K. Synthesis 1993, 735-762.
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14. Prepared by Simmons-Smith cyclopropanation of 5,17β-dihydroxy-11β-(4-methoxyphenyl)-5α-estr-9-en-3-one cyclic 2,2-dimethyl-1,3-pronanediyl acetal as described in: Neef, G.; Cleve, G.; Ottow, E.; Seeger, A.; Wiechert, R. J. Org. Chem. 1987, 52, 4143-4146.
15. AM1 structures have been proven to be in reasonable agreement with the X-ray crystal structures such as 24: Considering all non-hydrogen atoms of the steroid skeleton, a rms deviation of 0.14 Å has been calculated.
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18. The atomic co-ordinates and anisotropic displacement coefficients for this work are available on request from the Director of the Cambridge Crystallographic Data Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB2 1EW. Any request should be accompanied by the full literature citation for this publication.