- STRUCTURE-ACTIVITY RELATIONSHIPS OF ESTROGENS, EFFECTS OF 14-DEHYDROGENATION AND AXIAL METHYL GROUPS AT C-7, C-9 AND C-11
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Thirty compounds were evaluated in the rat for uterotropic effects, inhibition of gonadotropin release, and competitive displacement of (3H) estradiol-17β from uterine cytosolic preparations. 7α-Methylestradiol-17β was 150percent as active as estradiol-17β as an uterotropic agent.Estradiol-17β was the most active inhibitor of gonadotropin release. 11β-Methylestradiol-17β had 124percent of the activity of estradiol-17β in displacing (3H) estradiol-17β from the "estrogen receptor." The 9α-methyl group considerably decreased the potency of estrogens in any of the three assays.The 14-dehydromodification was advantageous only in the estradiol-17β 3-methyl ether series.Uterotropic activities and inhibition of gonadotropin release did not parallel.The best compound for inhibiting gonadotropin release, as compared to uterotropic activity, was estrone.The "estrogen receptor" assay data correlated fairly well with uterotropic assay data, but only for compounds having free 3-hydroxyl groups; even so, some exceptions were noted.
- Gabbard, R. Bruce,Segaloff, Albert
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- An expeditious route to 7α-substituted estradiol derivatives
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6-Ketoestradiol derivatives are converted in 7α-alkyl substituted estradiol derivatives selectively by alkylation of the generated enolate followed by deoxygenation-deprotection with BF3·Et2O/Et3SiH.
- Tedesco, Rosanna,Katzenellenbogen, John A.,Napolitano, Elio
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- PROCESS FOR THE PRODUCTION OF TIBOLONE
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Disclosed is a process for the synthesis of 17β-hydroxy-7α-methyl- 19-nor-17α-pregn-5(10)-ene-20-yne-3-one (tibolone, 11) and intermediates useful for the synthesis thereof: (11).
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- A NEW, STEREOSELECTIVE APPROACH TO C(7)-ALKYLATED ESTRA-1,3,5(10)-TRIENE DERIVATIVES
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17β-Acetyloxy-3-methoxy-6-(phenylsulfonyl)estra-1,3,5(10),6-tetraene (4) was prepared as a substrate for conjugate addition of organolithium reagents by a three-step sequence starting from 17β-acetyloxy-3-methoxyestra-1,3,5(10)-trien-6-one (2).While methy
- Kuenzer, H.,Thiel, M.,Sauer, G.,Wiechert, R.
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p. 1691 - 1694
(2007/10/02)
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- Stereocontrolled derivatization of 3-methoxyestra-1,3,5(10), n-tetraenes via lewis acid promoted prins reactions, (n=7; 8(9))
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Steroidal olefins 1 and 3 undergo dimethylaluminum chloride-mediated Prins reactions with paraformaldehyde to furnish homoallylic alcohols 4 and 16 as major products. These ene reaction-type intermediates are converted into 6 and 17 by hydroxyl group-assi
- Kuenzer, Hermann,Sauer, Gerhard,Wiechert, Rudolf
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p. 743 - 746
(2007/10/02)
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- Synthesis and testing of 17aβ-hydroxy-7α-methyl-D-homoestra-4,16-dien-3-one: a highly potent orally active androgen
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The title compound, 17aβ-hydroxy-7α-methyl-D-homoestra-4, 16-dien-3-one (3), was synthesized in five steps (17percent overall yield) from 7α-methylestrone methyl ether (5) and was found to possess oral androgenic activity, in excess of other known androgens, without using 17α-alkyl substitution. (Steroids 55:59-64, 1990)
- Avery, Mitchell A.,Tanabe, Masato,Crowe, David F.,Detre, George,Peters, Richard H.,Chong, Wesley K. M.
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