3-<3'-methoxy-17'β-(tert-butyldimethylsilyloxy)-1',3',5'(10')-estratrien-16'α-yl>propanol | 160840-43-7

• 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-(tert-butyldimethylsilyloxy)-1',3',5'(10')-estratrien-16'α-yl>propanol
• CAS: 160840-43-7
• 化学式: C₂₈H₄₆O₃Si
• 分子量: 458.757
• InChiKey: ZALSPGCEQAPVGT-SARKWJDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-<3'-methoxy-17'β-(tert-butyldimethylsilyloxy)-1',3',5'(10')-estratrien-16'α-yl>propanol 在 盐酸 、 sodium tetrahydroborate 、 jones reagent 、 三正丁胺 、 4 A molecular sieve 、 sodium acetate 、 三溴化硼 、 对甲苯磺酸 、 pyridinium chlorochromate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 14.75h， 生成 N-butyl, N-methyl, 11-<3',17'β-(dihydroxy)-1',3',5'(10')-estratrien-16'α-yl>-9(R/S)-bromoundecanamide
  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：

  3-<3'-methoxy-17'β-(tert-butyldimethylsilyloxy)-1',3',5'(10')-estratrien-16'α-yl>propene 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 生成 3-<3'-methoxy-17'β-(tert-butyldimethylsilyloxy)-1',3',5'(10')-estratrien-16'α-yl>propanol
  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