((R)-3-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)butyl)(imino)(phenyl)-l6-sulfanone | 635312-05-9

• 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: ((R)-3-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)butyl)(imino)(phenyl)-l6-sulfanone
• CAS: 635312-05-9
• 化学式: C₄₀H₆₉NO₃SSi₂
• 分子量: 700.23
• InChiKey: MZRPZTHKBBNFHP-AGUBURDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.15
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  59.38
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((R)-3-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)butyl)(imino)(phenyl)-l6-sulfanone 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以2.3 mg的产率得到(1R,3R)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol
  参考文献：
  名称：

  Potent, Selective and Low-Calcemic Inhibitors of CYP24 Hydroxylase:  24-Sulfoximine Analogues of the Hormone 1α,25-Dihydroxyvitamin D₃

  摘要：

  A dozen 24-sulfoximine analogues of the hormone 1alpha,25-dihydroxyvitamin D-3 were prepared, differing not only at the stereogenic sulfoximine stereocenter but also at the A-ring. Although these sulfoximines were not active transcriptionally and were only very weakly antiproliferative, some of them are powerful hydroxylase enzyme inhibitors. Specifically, 24-(S)-NH phenyl sulfoximine 3a is an extremely potent CYP24 inhibitor (IC50 = 7.4 nM) having low calcemic activity. In addition, this compound shows high selectivity toward the CYP24 enzyme in comparison to CYP27A1 (IC50 > 1000 nM) and CYP27B (IC50 = 554 nM).

  DOI：

  10.1021/jm040129+
• 作为产物：
  描述：

  (1R,3aR,4S,7aR)-7a-methyl-1-[(2R)-4-(phenylsulfonimidoyl)butan-2-yl]-1,2,3,3a,4,5,6,7-octahydroinden-4-ol 在 重铬酸吡啶 、 正丁基锂 、 Celite 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 ((R)-3-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)butyl)(imino)(phenyl)-l6-sulfanone
  参考文献：
  名称：

  Potent, Selective and Low-Calcemic Inhibitors of CYP24 Hydroxylase:  24-Sulfoximine Analogues of the Hormone 1α,25-Dihydroxyvitamin D₃

  摘要：

  A dozen 24-sulfoximine analogues of the hormone 1alpha,25-dihydroxyvitamin D-3 were prepared, differing not only at the stereogenic sulfoximine stereocenter but also at the A-ring. Although these sulfoximines were not active transcriptionally and were only very weakly antiproliferative, some of them are powerful hydroxylase enzyme inhibitors. Specifically, 24-(S)-NH phenyl sulfoximine 3a is an extremely potent CYP24 inhibitor (IC50 = 7.4 nM) having low calcemic activity. In addition, this compound shows high selectivity toward the CYP24 enzyme in comparison to CYP27A1 (IC50 > 1000 nM) and CYP27B (IC50 = 554 nM).

  DOI：

  10.1021/jm040129+