(20R,22R)-2β,3β-dihydroxy-20,22-isopropylidenedioxy-5α-cholestan-6-one | 1151467-48-9

• 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: (20R,22R)-2β,3β-dihydroxy-20,22-isopropylidenedioxy-5α-cholestan-6-one
• CAS: 1151467-48-9
• 化学式: C₃₀H₅₀O₅
• 分子量: 490.724
• InChiKey: FHJLTINYQQECPL-PDRMTZDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (20R,22R)-2β,3β-dihydroxy-20,22-isopropylidenedioxy-5α-cholestan-6-one 在 水 、 溶剂黄146 作用下， 反应 4.0h， 以71%的产率得到(20R,22R)-2β,3β,20,22-tetrahydroxy-5α-cholestan-6-one
  参考文献：
  名称：

  Synthesis of ponasterone A derivatives with various steroid skeleton moieties and evaluation of their binding to the ecdysone receptor of Kc cells

  摘要：

  A series of ponasterone A (PNA) derivatives with various steroid moieties were synthesized to measure their binding activity to the ecdysone receptors of Drosophila Kc cells. The activity of compounds was evaluated by deter-mining the concentration required to give the 50% inhibition (IC50 in M) of the incorporation of [H-3]PNA to Drosophila Kc cells. Compounds with no functional groups such as OH and C=O group in the steroid skeleton moiety were inactive. By the introduction of functional groups such as the OH and the C=O group in the steroidal structure, these compounds became active. Some compounds containing the A/B-trans ring fusion, which is different from that (A/B-cis) of ecdysteroids were also active. The oxidation of CH2 at 6-position to C=O, enhanced the activity 19 times, but the activity was erased by the reduction of oxo to OH group at 6-position. The activity was enhanced about 250 times by the conversion of A/B ring configuration from trans [(20R,22R)-2 beta,3 beta,20,22-tetrahydroxy-5 alpha-cholestan-6-one: pIC(50) = 4.84] to cis [(20R,22R)-2 beta,3 beta,20,22-tetrahydroxy-5 beta-cholestan-6-one: pIC(50) = 7.23]. The latter cis-type compound which is the most potent among compounds synthesized in this study was equipotent to the natural molting hormone, 20-hydroxyecdysone, even though it is 1/50 of PNA. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.08.005
• 作为产物：
  描述：

  (20R,22R,23R)-22,23-epoxy-3β-(tert-butyldimethylsilyl)oxycholest-5-en-20-ol 在 吡啶 、 chromium(VI) oxide 、 四氧化锇 、 lithium aluminium tetrahydride 、 N-甲基吲哚酮 、 dimethyl sulfide borane 、 硫酸 、 四丁基氟化铵 、 lithium carbonate 、 对甲苯磺酸 、 lithium bromide 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， 反应 146.83h， 生成 (20R,22R)-2β,3β-dihydroxy-20,22-isopropylidenedioxy-5α-cholestan-6-one
  参考文献：
  名称：

  立体选择性合成（22R）-和（22S）-castasterone / ponasterone A杂化化合物并评估其蜕皮激素活性。

  摘要：

  立体选择性地合成了一种栗甾酮/ ponasterone A杂合化合物的两种立体异构体，即2alpha，3alpha，20,22-tetrahydroxy-5alpha-cholestan-6-one的（20R，22R）和（20R，22S）-异构体确定了对蜕皮甾类受体的活性。从用于抑制of化的ponasterone A掺入含蜕皮类固醇受体的昆虫细胞的浓度-响应曲线，评估抑制50％的放射性掺入细胞所需的浓度（IC50）。（22R）-和（22S）-异构体对Kc细胞的IC50值分别确定为0.30和38.9 microM，表明（22R）-异构体的效价比相应的（22S）-异构体的效价高约100倍异构体。这些化合物对鳞翅目Sf-9细胞的IC50值确定为0.36和12。分别为9 microM。在Chilohibialis皮层系统中检查了蜕皮激素的作用，对于（22R）-异构体刺激N-乙酰氨基葡萄糖掺入培养的皮层的50％有效浓度确定为2

  DOI：

  10.1016/j.steroids.2004.04.005