25-Hydroxy-26,26,26,27,27,27-hexafluorovitamin D3 | 75303-43-4

• 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: 25-Hydroxy-26,26,26,27,27,27-hexafluorovitamin D3
• 英文别名: 26,26,26,27,27,27-hexafluoro-25-hydroxyvitamin D3/26,26,26,27,27,27-hexafluoro-25-hydroxycholecalciferol；(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-7,7,7-trifluoro-6-hydroxy-6-(trifluoromethyl)heptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• CAS: 75303-43-4
• 化学式: C₂₇H₃₈F₆O₂
• 分子量: 508.588
• InChiKey: UYSBDEYGNDFSLX-CSWVGKENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25-Hydroxy-26,26,26,27,27,27-hexafluorovitamin D3 在 氧气 、 rose bengal 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.25h， 以40%的产率得到26,26,26,27,27,27-hexafluoro-25-hydroxy-6,19-dihydro-6,19-epidioxyvitamin D₃
  参考文献：
  名称：

  Syntheses and differentiating action of vitamin D endoperoxides. Singlet oxygen adducts of vitamin D derivatives in human myeloid leukemia cells (HL-60)

  摘要：

  Singlet oxygen adducts of various vitamin D derivatives, 6,19-dihydro-6,19-epidioxyvitamin D (vitamin D endoperoxides, 2 and 2'), were chemically synthesized, and their biological activity in inducing differentiation of a human myeloid leukemia cell line (HL-60 cells) was examined. The potency of the endoperoxides derived from vitamin D derivatives possessing the 1 alpha-hydroxyl group such as 1 alpha, 25-dihydroxyvitamin D3 endoperoxides (2b and 2b') was markedly (10(-2)) diminished relative to the respective parent vitamin D compounds. In contrast, 25-hydroxyvitamin D3 endoperoxides [25-(OH)D3 endoperoxides, 2a and 2a'] and their analogues fluorinated at the 24- or 26- and 27-positions were 2.5-10 times more potent than 25-hydroxyvitamin D3 (1a) in spite of the absence of the conjugated triene structure typical of vitamin D compounds. The potency of these vitamin D endoperoxides (2 and 2'), especially those lacking the 1 alpha-hydroxyl group, in inducing differentiation of HL-60 cells was not correlated with their activity in binding to the cytosol receptor for 1 alpha, 25-dihydroxyvitamin D3 (1b). The binding efficiency to the receptor was relatively lower than the differentiating activity. To examine the action of vitamin D endoperoxides, carbon analogues of 25-(OH)D3 endoperoxides, two C-6 epimers of 25-hydroxy-6,19-dihydro-6,19-ethanovitamin D3 (6 and 6'), were synthesized. The carbon analogues (6 and 6') had no potential to induce differentiation of HL-60 cells. These results suggest that vitamin D endoperoxides (2 and 2') express their biological activity probably after being converted to some other compounds.

  DOI：

  10.1021/jm00147a005

文献信息

• Composition for solid pharmaceutical preparations of active vitamins D3 and process for preparation thereof
  申请人：TEIJIN LIMITED

  公开号：EP0116755B1

  公开（公告）日：1987-08-05
• US4248791A
  申请人：——

  公开号：US4248791A

  公开（公告）日：1981-02-03
• US4594192A
  申请人：——

  公开号：US4594192A

  公开（公告）日：1986-06-10
• US4613594A
  申请人：——

  公开号：US4613594A

  公开（公告）日：1986-09-23
• US4729895A
  申请人：——

  公开号：US4729895A

  公开（公告）日：1988-03-08