(8S,20S)-des-A,B-22-cyano-8β,25-bis[(triethylsilyl)oxy]cholestane | 1335097-34-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (8S,20S)-des-A,B-22-cyano-8β,25-bis[(triethylsilyl)oxy]cholestane
• 英文别名: (8S,20S)-des-A,B-8-[(triethylsilyl)oxy]-22-cyano-25-[(triethylsilyl)oxy]cholestane；2-[(1S)-1-[(1R,3aR,4S,7aR)-7a-methyl-4-triethylsilyloxy-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]ethyl]-5-methyl-5-triethylsilyloxyhexanenitrile
• CAS: 1335097-34-1
• 化学式: C₃₁H₆₁NO₂Si₂
• 分子量: 536.002
• InChiKey: GLFSXUCIOVWLHI-MGWWHURRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.95
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,20S)-des-A,B-22-cyano-8β,25-bis[(triethylsilyl)oxy]cholestane 在 二异丁基氢化铝 、 水 、 rochelle salt 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (8S,20S,22R)-des-A,B-22-formyl-8β,25-bis[(triethylsilyl)oxy]cholestane 、 (8S,20S,22S)-des-A,B-22-formyl-8β,25-bis[(triethylsilyl)oxy]cholestane
  参考文献：
  名称：

  DIASTEREOMERS OF 2-METHYLENE-19-NOR-22-METHYL-1ALPHA,25-DIHYDROXYVITAMIN D3

  摘要：

  提供了公式I的化合物，其中X1、X2和X3分别选自H或羟基保护基团。这些化合物可用于制备药物组合物，并可用于治疗各种生物状况。

  公开号：

  US20110237557A1

文献信息

• A 20<i>S</i> Combined with a 22<i>R</i> Configuration Markedly Increases both in Vivo and in Vitro Biological Activity of 1α,25-Dihydroxy-22-methyl-2-methylene-19-norvitamin D₃
  作者：Agnieszka Flores、Rafal R. Sicinski、Pawel Grzywacz、James B. Thoden、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1021/jm300187x

  日期：2012.5.10

  Six new analogues of 1 alpha,25-dihydroxy-19-norvitamin D-3 (3a-4b, 5, and 6) were prepared by a convergent synthesis applying the Wittig-Horner reaction as a key step. The influence of methyl groups at C-22 on their biological activity was examined. It was established that both in vitro and in vivo activity is strongly dependent on the configuration of the stereogenic centers at C-20 and C-22. Introduction of the second methyl group at C-22 (analogues 5 and 6) generates the compounds that are slightly more potent than 1 alpha,25-(OH)(2)D-3 in the in vitro tests but much less potent in vivo. The greatest in vitro and in vivo biological activity was achieved when the C-20 is in the S configuration and the C-22 is in the R configuration. The building blocks for the synthesis, the respective (20R,22R)-, (20R,22S)-, (20S,22R)-, and (20S,22S)-diols, were obtained by fractional crystallization of mixtures of the corresponding diastereomers. Structures and absolute configurations of the diols 21a, 21b, and 22a as well as analogues 3a, 5, and 6 were confirmed by the X-ray crystallography.