(E)-3β-hydroxy-17-picolinylideneandrost-5-ene-16-one | 960313-59-1

• 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: (E)-3β-hydroxy-17-picolinylideneandrost-5-ene-16-one
• 英文别名: (3S,8R,9S,10R,13S,14S,17E)-3-hydroxy-10,13-dimethyl-17-(pyridin-2-ylmethylidene)-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-16-one
• CAS: 960313-59-1
• 化学式: C₂₅H₃₁NO₂
• 分子量: 377.527
• InChiKey: HYUIINJTBIMMRR-XQGZVWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3β-hydroxy-17-picolinylideneandrost-5-ene-16-one 在 aluminum tri-tert-butoxide 作用下， 以 环己酮 为溶剂， 反应 35.0h， 以36%的产率得到(E)-17-picolinylideneandrost-4-ene-3,16-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives

  摘要：

  Starting from dehydroepiandrosterone (1) 17-picolyl (2), 17-picolinylidene (7), 17-picolinylidene-16-one (10 and 11), and 17-picolyl-16-one (15) derivatives of androst-5-ene were synthesized in one, two, four and five steps respectively. By the Oppenauer oxidation or dehydration of 2, 7, 10, and 11 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the corresponding A and B ring modified derivatives 3, 5, 6, 8, 9, and 12-14 were obtained. The structure of 2 was unambiguously proved by the appropriate X-ray structural analysis. Compounds 3, 5,9,12-14 showed inhibitory activity against the enzyme aromatase. Antibacterial activity toxicity to brine shrimp Artemia salina, antitumor activity against three tumor cell lines (human cervix carcinoma HeLa cells, human melanoma FemX cells, and human myelogenous leukemia K562 cells) and toxicity against peripheral blood mononuclear cells were evaluated. Three tested compounds, namely 11, 13, and 15, showed strong activity against all three cell lines, the IC50 values being in the range of 4-10 mu M. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.10.002
• 作为产物：
  描述：

  Acetic acid (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-16-oxo-17-[1-pyridin-2-yl-meth-(E)-ylidene]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以78%的产率得到(E)-3β-hydroxy-17-picolinylideneandrost-5-ene-16-one
  参考文献：
  名称：

  Synthesis and biological evaluation of some 17-picolyl and 17-picolinylidene androst-5-ene derivatives

  摘要：

  Starting from dehydroepiandrosterone (1) 17-picolyl (2), 17-picolinylidene (7), 17-picolinylidene-16-one (10 and 11), and 17-picolyl-16-one (15) derivatives of androst-5-ene were synthesized in one, two, four and five steps respectively. By the Oppenauer oxidation or dehydration of 2, 7, 10, and 11 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the corresponding A and B ring modified derivatives 3, 5, 6, 8, 9, and 12-14 were obtained. The structure of 2 was unambiguously proved by the appropriate X-ray structural analysis. Compounds 3, 5,9,12-14 showed inhibitory activity against the enzyme aromatase. Antibacterial activity toxicity to brine shrimp Artemia salina, antitumor activity against three tumor cell lines (human cervix carcinoma HeLa cells, human melanoma FemX cells, and human myelogenous leukemia K562 cells) and toxicity against peripheral blood mononuclear cells were evaluated. Three tested compounds, namely 11, 13, and 15, showed strong activity against all three cell lines, the IC50 values being in the range of 4-10 mu M. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.10.002