3β-n-butyl-17β-[(tert-butyldimethylsilyl)oxy]-3α-hydroxy-5α-androstane | 863659-38-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3β-n-butyl-17β-[(tert-butyldimethylsilyl)oxy]-3α-hydroxy-5α-androstane
• CAS: 863659-38-5
• 化学式: C₂₉H₅₄O₂Si
• 分子量: 462.832
• InChiKey: CFTCBXJUXDTVST-XRMBPXMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  3β-n-butyl-17β-[(tert-butyldimethylsilyl)oxy]-3α-hydroxy-5α-androstane 在 盐酸 、 jones' reagent 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.5h， 生成 3β-n-butyl-3α-hydroxy-5α-androstan-17-one
  参考文献：
  名称：

  Androsterone 3α-Ether-3β-Substituted and Androsterone 3β-Substituted Derivatives as Inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase:  Chemical Synthesis and Structure−Activity Relationship

  摘要：

  Type 3 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) is involved in the biosynthesis of androgen testosterone. To produce potent inhibitors of this key steroidogenic enzyme, we prepared a series of androsterone (ADT) derivatives by adding a variety of substituents at position 3. The 3 beta-substituted ADT derivatives proved to be good inhibitors (IC50 = 57-147 nM) with better inhibitory activities obtained for compounds bearing a propyl, s-butyl, cyclohexylalkyl, or phenylalkyl group. With an IC50 value of 57 nM, the 3 beta-phenylmethyl-ADT was 6-fold more potent than ADT, the lead compound, and 13-fold more potent than 4-androstene-3,17-dione, the natural enzyme substrate used itself as inhibitor. The 3 alpha-ether-3 beta-substituted ADT derivatives had a lower inhibitory activity compared to the 3 beta-substituted ADT analogues except for the 3 beta-phenylethyl-3 alpha-methl-O-ADT (IC50 = 73 nM), which proved to be a more potent inhibitor than 3 beta-phenylethyl-ADT (IC50 = 99 nM). The results of our study identified potent type 3 17 beta-HSD inhibitors for potential use in the treatment of androgen-sensitive diseases.

  DOI：

  10.1021/jm058179h
• 作为产物：
  描述：

  雄诺龙 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3β-n-butyl-17β-[(tert-butyldimethylsilyl)oxy]-3α-hydroxy-5α-androstane
  参考文献：
  名称：

  Androsterone 3α-Ether-3β-Substituted and Androsterone 3β-Substituted Derivatives as Inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase:  Chemical Synthesis and Structure−Activity Relationship

  摘要：

  Type 3 17 beta-hydroxysteroid dehydrogenase (17 beta-HSD) is involved in the biosynthesis of androgen testosterone. To produce potent inhibitors of this key steroidogenic enzyme, we prepared a series of androsterone (ADT) derivatives by adding a variety of substituents at position 3. The 3 beta-substituted ADT derivatives proved to be good inhibitors (IC50 = 57-147 nM) with better inhibitory activities obtained for compounds bearing a propyl, s-butyl, cyclohexylalkyl, or phenylalkyl group. With an IC50 value of 57 nM, the 3 beta-phenylmethyl-ADT was 6-fold more potent than ADT, the lead compound, and 13-fold more potent than 4-androstene-3,17-dione, the natural enzyme substrate used itself as inhibitor. The 3 alpha-ether-3 beta-substituted ADT derivatives had a lower inhibitory activity compared to the 3 beta-substituted ADT analogues except for the 3 beta-phenylethyl-3 alpha-methl-O-ADT (IC50 = 73 nM), which proved to be a more potent inhibitor than 3 beta-phenylethyl-ADT (IC50 = 99 nM). The results of our study identified potent type 3 17 beta-HSD inhibitors for potential use in the treatment of androgen-sensitive diseases.

  DOI：

  10.1021/jm058179h

文献信息

• Construction of a quaternary carbon at the carbonyl carbon of the cyclohexane ring
  作者：Yuki Kaneko、Yohei Kiyotsuka、Hukum P. Acharya、Yuichi Kobayashi

  DOI：10.1039/c0cc00653j

  日期：——

  High S(N)2' selectivity in the allylic substitution of cyclohexylidene ethyl picolinates with copper reagents prepared from RMgBr and CuBr.Me(2)S was realized by addition of ZnX(2) (X = I, Br, Cl). Furthermore, ZnX(2) accelerated the reaction with the bulky iPr reagent.

  通过添加ZnX（2）（X = I，Br，Cl）实现了用RMgBr和CuBr.Me（2）S制备的铜试剂对环己叉基乙基吡啶甲酸乙酯进行烯丙基取代的高S（N）2'选择性。此外，ZnX（2）促进了与庞大的iPr试剂的反应。