1,4-androstadien-3β,17β-diol | 34195-01-2

• 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: 1,4-androstadien-3β,17β-diol
• 英文别名: androsta-4,6-diene-3β,17β-diol；1,4,6-androstatrien-3β,17β-diol；Androsta-4,6-dien-3β,17β-diol；(3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 34195-01-2
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: BVWPXNVCXHPUNN-LOVVWNRFSA-N

物化性质

• 熔点：
  194-196 °C
• 沸点：
  447.0±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-androstadien-3β,17β-diol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以64%的产率得到4β,5β-epoxyandrost-6-en-3β,17β-diol
  参考文献：
  名称：

  Ma, Eunsook; Kim, Eunjeong, Molecules, 2005, vol. 10, # 3, p. 794 - 804

  摘要：

  DOI：
• 作为产物：
  描述：

  去氢表雄酮 在 sodium tetrahydroborate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 24.0h， 生成 1,4-androstadien-3β,17β-diol
  参考文献：
  名称：

  Ma, Eunsook; Kim, Eunjeong, Molecules, 2005, vol. 10, # 3, p. 794 - 804

  摘要：

  DOI：

文献信息

• Synthesis of 2- and 7- Substituted C19 Steroids Having a 1,4,6-Triene or 1,4-Diene Structure and Their Cytotoxic Effects on T47D and MDA-MB231 Breast Cancer Cells
  作者：Minwoo Kim、Eunsook Ma

  DOI：10.3390/molecules15064408

  日期：——

  2-Chloro-, 2-bromo- and 2-azido-1,4,6-androstatriene-3,17-diones were synthesized from 1α,2α-epoxy-4,6-androstadiene-3,17-dione (2) using HCl, HBr and NaN3, respectively. Compound 2 was also reacted with NaCN to give 2-cyano-1,4,6-androstatriene-3,17-dione (5) and 2β-cyano-1α-hydroxy-4,6-androstadiene-3,17-dione (6). 6α,7α-Epoxy-1,4-androstadiene-3,17-dione (8) was reacted with HCl, HBr and NaN3 to form the corresponding 7β-chloro-, 7β-bromo- and 7β-azido-6α-hydroxy-1,4-androstadiene-3,17-diones. The cytotoxic activity of these compounds towards T47D (estrogen-dependent) and MDA-MB231 (estrogen-independent) breast cancer cell lines was evaluated. The 6α-hydroxy-7β-substituted analogs were more active than the 2-substituted analogs on both cell lines. Compound 2 showed the highest selective activity against the T47D (IC50 7.1 μM) cell line and 5 showed good cytotoxic activity on MDA-MB231 (IC50 18.5 μM) cell line, respectively. The 6α,7α-epoxy analog 8 also showed high cytotoxic activity on both cell lines (IC50 17.3 μM on T47D and IC50 26.9 μM on MDA-MB231).

  用 HCl、HBr 和 NaN3 分别从 1α,2α-环氧-4,6-雄甾二烯-3,17-二酮 (2) 合成 2-氯、2-溴和 2-叠氮-1,4,6-雄甾二烯-3,17-二酮。化合物 2 还与 NaCN 反应，得到 2-氰基-1,4,6-雄甾二烯-3,17-二酮 (5) 和 2β-氰基-1α-羟基-4,6-雄甾二烯-3,17-二酮 (6)。6α,7α-环氧-1,4-雄甾二烯-3,17-二酮（8）与 HCl、HBr 和 NaN3 反应生成相应的 7β-氯、7β-溴和 7β-叠氮-6α-羟基-1,4-雄甾二烯-3,17-二酮。评估了这些化合物对 T47D（雌激素依赖型）和 MDA-MB231（雌激素非依赖型）乳腺癌细胞系的细胞毒活性。与 2-取代类似物相比，6α-羟基-7β-取代类似物对这两种细胞株的活性更高。化合物 2 对 T47D（IC50 为 7.1 μM）细胞系的选择性活性最高，而化合物 5 则分别对 MDA-MB231 （IC50 为 18.5 μM）细胞系表现出良好的细胞毒性活性。6α,7α-环氧类似物 8 对这两种细胞系也显示出较高的细胞毒性活性（对 T47D 的 IC50 为 17.3 μM，对 MDA-MB231 的 IC50 为 26.9 μM）。
• Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents
  作者：Eunjeong Kim、Eunsook Ma

  DOI：10.1016/j.steroids.2006.12.008

  日期：2007.4

  The chemoselectivity of rigid cyclic alpha,omega-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3 beta-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (L-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3.(CH3)(2)S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3 beta-ol and 4,6-androstadiene-3 beta,17 beta-diol, respectively Reduction by L-Selectride (12 equiv.) afforded 4,6-cholestadien-3 alpha-ol and 4,6-androstadiene-3 alpha,17 beta-diol, chemoselectively Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17 beta-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3 alpha-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3 beta-ol and 3-oxo-1,4,6-androstatrien-17 beta-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3.(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3.(CH3)(2)s formed 3-oxo-1,4,6-androstatrien-17 beta-ol. LiAlH4 and BH3.(CH3)(2)S showed relatively low chemoselectivity. (c) 2007 Elsevier Inc. All rights reserved.
• Steroids. XXI.¹ Δ⁷-Androstene-3β,17β-diol
  作者：F. Neumann、G. Rosenkranz、J. Romo、Carl Djerassi

  DOI：10.1021/ja01155a546

  日期：1951.11
• Holland, Herbert L.; Chenchaiah, P. Chinna; Thomas, Everton M., Canadian Journal of Chemistry, 1984, vol. 62, p. 2740 - 2747
  作者：Holland, Herbert L.、Chenchaiah, P. Chinna、Thomas, Everton M.、Mader, Beatrix、Dennis, Michael J.

  DOI：——

  日期：——