(3aR,4S,7aS)-1-((R)-5-Ethyl-4,4-difluoro-5-hydroxy-1-methyl-heptyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol | 212124-53-3

• 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: (3aR,4S,7aS)-1-((R)-5-Ethyl-4,4-difluoro-5-hydroxy-1-methyl-heptyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol
• CAS: 212124-53-3
• 化学式: C₂₀H₃₄F₂O₂
• 分子量: 344.486
• InChiKey: WUCQONRRCGXRCK-LAVFITLUSA-N

物化性质

• 沸点：
  437.5±45.0 °C(predicted)
• 密度：
  1.076±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7aS)-1-((R)-5-Ethyl-4,4-difluoro-5-hydroxy-1-methyl-heptyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol 在 重铬酸吡啶 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到(3aR,7aS)-1-((R)-5-Ethyl-4,4-difluoro-5-hydroxy-1-methyl-heptyl)-7a-methyl-3,3a,5,6,7,7a-hexahydro-inden-4-one
  参考文献：
  名称：

  Noncalcemic, Antiproliferative, Transcriptionally Active, 24-Fluorinated Hybrid Analogues of the Hormone 1α,25-Dihydroxyvitamin D₃. Synthesis and Preliminary Biological Evaluation

  摘要：

  Four new hybrid analogues of 1 alpha,25-dihydroxyvitamin D-3 (1) have been synthesized in a convergent manner by joining A-ring and C,D-ring fragments. Each hybrid analogue, having a noncalcemic 1-hydroxymethyl group and a potentiating 16-ene 24,24-difluorinated C,D-ring side chain, was designed to be lipophilic and inert toward 24-hydroxylase enzyme catabolism. Each hybrid analogue with 1 beta,3 alpha-substituent stereochemistry (i.e., analogues 3b and 4b) showed a pharmacologically desirable combination of in vitro high antiproliferative activity in two different cell lines and high transcriptional activity with also low calcemic activity in vivo.

  DOI：

  10.1021/jm980031t
• 作为产物：
  描述：

  ethyl (5R)-5-[(3aR,4S,7aS)-7a-methyl-4-triethylsilyloxy-3,3a,4,5,6,7-hexahydroinden-1-yl]-2,2-difluorohexanoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (3aR,4S,7aS)-1-((R)-5-Ethyl-4,4-difluoro-5-hydroxy-1-methyl-heptyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol
  参考文献：
  名称：

  Noncalcemic, Antiproliferative, Transcriptionally Active, 24-Fluorinated Hybrid Analogues of the Hormone 1α,25-Dihydroxyvitamin D₃. Synthesis and Preliminary Biological Evaluation

  摘要：

  Four new hybrid analogues of 1 alpha,25-dihydroxyvitamin D-3 (1) have been synthesized in a convergent manner by joining A-ring and C,D-ring fragments. Each hybrid analogue, having a noncalcemic 1-hydroxymethyl group and a potentiating 16-ene 24,24-difluorinated C,D-ring side chain, was designed to be lipophilic and inert toward 24-hydroxylase enzyme catabolism. Each hybrid analogue with 1 beta,3 alpha-substituent stereochemistry (i.e., analogues 3b and 4b) showed a pharmacologically desirable combination of in vitro high antiproliferative activity in two different cell lines and high transcriptional activity with also low calcemic activity in vivo.

  DOI：

  10.1021/jm980031t