用于亲和标记的溴乙酸甲羟孕酮的合成。

Synthesis of medroxyprogesterone bromoacetate for affinity labeling.

作者信息

Samant B R, Sweet F

出版信息

J Med Chem. 1977 Jun;20(6):833-5. doi: 10.1021/jm00216a019.

DOI:10.1021/jm00216a019

Abstract

Medroxyprogesterone bromoacetate (17alpha-hydroxy-6alpha-methyl-4-pregnene-3,20-dione 17-bromoacetate) was synthesized by reaction of 17alpha-hydroxy-6alpha-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 20beta-hydroxy steroid dehydrogenase (E.C. 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.

摘要

溴醋酸甲羟孕酮（17α-羟基-6α-甲基-4-孕烯-3,20-二酮17-溴醋酸酯）通过17α-羟基-6α-甲基-4-孕烯-3,20-二酮与溴乙酸-三氟乙酸酐反应，随后用稀乙醇溴化氢处理中间体而合成。该产物与L-半胱氨酸、L-组氨酸和L-蛋氨酸形成缀合物，并以时间依赖性和不可逆的方式使来自氢化链霉菌的20β-羟基类固醇脱氢酶（E.C. 1.1.1.53.）失活。标题化合物在双侧卵巢切除的妊娠第9天大鼠中具有长效孕激素作用。提出将口服避孕药醋酸甲羟孕酮的亲和标记类似物用于生殖生物学实验。

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