(20R,22R)-2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D₃ | 1335097-51-2

• 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: (20R,22R)-2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D₃
• 英文别名: (20R,22R)-1α,25-dihydroxy-22-methyl-2-methylene-19-norvitamin D(3)；(1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,3R)-6-hydroxy-3,6-dimethylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2-methylidenecyclohexane-1,3-diol
• CAS: 1335097-51-2
• 化学式: C₂₈H₄₆O₃
• 分子量: 430.671
• InChiKey: GDUKBQQIBUKNKX-FTKZSCHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (20R,22R)-des-A,B-22-methyl-25-[(triethylsilyl)oxy]cholestan-8-one 在 氢氟酸 、 苯基锂 作用下， 以 四氢呋喃 、 二丁醚 、 水 、 乙腈 为溶剂， 反应 25.5h， 生成 (20R,22R)-2-methylene-19-nor-22-methyl-1α,25-dihydroxyvitamin D₃
  参考文献：
  名称：

  A 20S Combined with a 22R Configuration Markedly Increases both in Vivo and in Vitro Biological Activity of 1α,25-Dihydroxy-22-methyl-2-methylene-19-norvitamin D₃

  摘要：

  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.

  DOI：

  10.1021/jm300187x

文献信息

• DIASTEREOMERS OF 2-METHYLENE-19-NOR-22-METHYL-1ALPHA,25-DIHYDROXYVITAMIN D3
  申请人：DeLuca Hector F.

  公开号：US20110237557A1

  公开（公告）日：2011-09-29

  Compounds of formula I are provided where X 1 , X 2 , and X 3 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

  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。