3-<3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratrien-16'β-yl>propene | 33765-74-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-<3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratrien-16'β-yl>propene
• 英文别名: 16β-allylestradiol 3-methyl ether
• CAS: 33765-74-1
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: XGMMTQVTWSYWIL-ZCHQJCHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-<3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratrien-16'β-yl>propene 在 4 A molecular sieve 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到3-<3'-methoxy-17'-oxo-1',3',5'(10')-estratrien-16'β-yl>propene
  参考文献：
  名称：

  N-butyl, N-methyl, 11-[3′,17′ β-(dihydroxy)-1′,3′,5′(10′)- estratrien-16′ α-yl]-9(R/S)-bromo undecanamide: synthesis and 17β-HSD inhibiting, estrogenic and antiestrogenic activities

  摘要：

  The synthesis of a 16 alpha-(bromoalkylamide) derivative of estradiol (N-butyl, N-methyl, 11-[3',17'beta-(dihydroxy)-1',3',5'(10')-estratrien-16'alpha-yl]-9(R/S)-bromo undecanamide) was performed by two different approaches starting from estrone. Each approach hers the same key intermediate, containing an aldehyde group, but differs by the bromination step and the timing of formation of the amide group. This compound was found to cause, at 100 mu M, a complete inhibition of 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) responsible for the interconversion of estrone and estradiol. The corresponding IC50 value was 10.6 mu M. In the estrogen-sensitive ZR-75-1 human breast cancer cell line, this estradiol derivative has no estrogenic activity at 30 nM and only a minimal estrogenic activity (10% above the basal level) at 1 mu M. At this latter concentration, this compound causes a 28% inhibition of 0.1 nM EI-induced cel[proliferation (antiestrogenic activity). Thus, the introduction of a side-chain with a secondary bromide and a butyl methyl amide group at the 16 alpha-position of estradiol has two interesting effects; namely an inhibition of cytosolic 17 beta-HSD and a blockade of the estrogenic effect of estradiol.

  DOI：

  10.1016/0039-128x(94)90072-8
• 作为产物：
  描述：

  (8R,9S,13S,14S,16S,17R)-16-Allyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-16,17-diol 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 3-<3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratrien-16'β-yl>propene
  参考文献：
  名称：

  A Stereoselective Synthesis of 16β-Substituted-17-oxosteroids

  摘要：

  DOI：

  10.1248/cpb.21.1393

文献信息

• Synthesis and antiandrogenic activity of 16.BETA.-substituted-17.BETA.-hydroxysteroids.
  作者：GIICHI GOTO、KOUICHI YOSHIOKA、KENTARO HIRAGA、MICHIO MASUOKA、RYO NAKAYAMA、TAKUICHI MIKI

  DOI：10.1248/cpb.26.1718

  日期：——

  In order to examine the antiandrogenic activity, a series of 16β-substituted-17β-hydroxysteroids (9 and 16) were synthesized by stereoselective introduction of β-substituents at position 16 of steroids. The corresponding 6-chloro-16β-substituted-17β-hydroxysteroids (20 and 28) and 1, 2α-methylene derivative (36) were also prepared. Among these new steroids synthesized, 17β-hydroxy-16β-ethylestr-4-en-3-one (9b : TSAA-291) was found to have the most potent antiandrogenic activity with very weak side effects and also found to be useful for a treatment of the benign prostatic hypertrophy.

  为了研究其抗雄激素活性，通过在类固醇的第 16 位立体选择性地引入 β 取代基，合成了一系列 16β 取代基-17β-羟基类固醇（9 和 16）。此外，还制备了相应的 6-氯-16β-取代-17β-羟基类固醇（20 和 28）以及 1，2α-亚甲基衍生物（36）。在合成的这些新类固醇中，17β-羟基-16β-乙基雌甾-4-烯-3-酮（9b：TSAA-291）具有最强的抗雄激素活性，且副作用极小，还可用于治疗良性前列腺肥大。