24,24-Difluoro-25-hydroxyvitamin D3 | 71603-41-3

• 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: 24,24-Difluoro-25-hydroxyvitamin D3
• 英文别名: 24,24-difluoro-25-hydroxyvitamin D3/24,24-difluoro-25-hydroxycholecalciferol；(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-5,5-difluoro-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• CAS: 71603-41-3
• 化学式: C₂₇H₄₂F₂O₂
• 分子量: 436.626
• InChiKey: LRNVEDCUBISUTC-CMOHYRQESA-N

物化性质

• 沸点：
  545.1±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  24,24-Difluoro-25-hydroxyvitamin D3 在 氧气 、 rose bengal 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.0h， 以31%的产率得到24,24-difluoro-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
• 作为产物：
  描述：

  3β-acetoxy-24,24-difluoro-27-norcholest-5-en-25-one 在 吡啶 、 2,4,6-三甲基吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 51.96h， 生成 24,24-Difluoro-25-hydroxyvitamin D3
  参考文献：
  名称：

  Kobayashi, Yoshiro; Taguchi, Takeo; Terada, Tadafumi, Journal of the Chemical Society. Perkin transactions I, 1982, p. 85 - 92

  摘要：

  DOI：

文献信息

• 23,23-DIFLUORO-25-HYDROXY-VITAMIN D 3? AND PROCESS FOR PREPARING SAME
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：EP0154627A1

  公开（公告）日：1985-09-18
• THERAPEUTIC COMPOSITIONS FOR OSTEOINDUCTION
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP0587751A1

  公开（公告）日：1994-03-23
• US4196133A
  申请人：——

  公开号：US4196133A

  公开（公告）日：1980-04-01
• US4305880A
  申请人：——

  公开号：US4305880A

  公开（公告）日：1981-12-15
• US4336193A
  申请人：——

  公开号：US4336193A

  公开（公告）日：1982-06-22