Synthesis of medroxyprogesterone bromoacetate for affinity labeling
- 1 June 1977
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 20 (6) , 833-835
- https://doi.org/10.1021/jm00216a019
Abstract
Medroxyprogesterone bromoacetate (17.alpha.-hydroxy-6.alpha.-methyl-4-pregnene-3,20-dione 17-bromoacetate) was synthesized by reaction of 17.alpha.-hydroxy-6.alpha.-methyl-4-pregnene-3,20-dione with bromoacetic acid-trifluoroacetic anhydride followed by treatment of the intermediate with dilute ethanolic HBr. The product forms conjugates with L-cysteine, L-histidine and L-methionine and inactivates 20.beta.-hydroxy steroid dehydrogenase (EC 1.1.1.53) from Streptomyces hydrogenans in a time-dependent and irreversible manner. The title compound possesses a long-acting progestational effect in day 9 pregnant bilaterally ovariectomized rats. The affinity labeling analogue of the oral contraceptive medroxyprogesterone acetate is proposed for use in reproductive biological experiments.This publication has 0 references indexed in Scilit: