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The progestin dienogest (17α-cyanomethyl-17β-hydroxy-estra-4,9-dien-3-one) was metabolized by the nitrile hydratase-containing microorganism Rhodococcus erythropolis. An enzymatic hydrolysis of the nitrile group at the 17α-side chain was intended to obtain novel derivatives and to test them for progesterone receptor affinity. In contrast to the rapid enzymatic hydrolysis of nonsteroidal nitriles,...
The title compound 17 has been synthesized for the use as hapten in the development of a competitive enzyme immunoassay for estrogen sulfamates. The synthesis started from estradiol diacetate 2. Oxyfunctionalization at C-11 to give 11α-hydroxy steroid 8 was accomplished by hydroboration/alkaline hydrogen peroxide oxidation of the 9(11)-dehydro derivative 7, which was obtained from compound 2 via 9-hydroxylation...
To improve the weak inhibitory effect of 3-oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) on Na + /K + -ATPase activity in human heart muscle, we have investigated the impact of hydrogenation, reduction, glycosidation, and the introduction of a 3-sulfonamido residue on the inhibitory potency of canrenone. The greatest increase in potency (>20 times) was found for 3β-(α-l-rhamnopyranosyloxy)-5β,17α-pregnane-21,17-carbolactone...
3-Oxo-17α-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17α-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone...
Estrogen sulfamates are promising hormones by oral administration. Therefore, generally applicable and convenient methods for the multigram synthesis of these derivatives are desirable. Numerous estra-1,3,5(10)-trienes derived from estrone, estradiol, 14α,15α-methylenestradiol, ethinylestradiol, and estriol have been esterified with sulfamoyl chloride and N-methylsulfamoyl chloride by a novel approach...
3-Methoxy-14α, 15α-methylenestra-1,3,5(10),8-tetraen-17α-ol on hydrogenation with triethylsilane/trifluoroacetic acid yielded 3-methoxy-14β,15β-methylenestra-1,3,5(10)-trien-17α-ol, not the 14α,15α-methylene-9βproduct as previously described . (Steroids 61:48-49, 1996)
A novel approach to the synthesis of the orally active estrogen 14α,15α-methylene estradiol (8, J 824) is described, starting with 3-methoxy-estra-1,3,5(10),8,14-pentaen-17α-ol(5). The 14α,15α-methylene bridge was sonochemically introduced by regioselective and stereoselective Simmons-Smith methylenation of the 14-double bond. Birch reduction of the 8-double bond provided the desired 8β-H, 9α-H...
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