[[[(3R)-3-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butyl]-(4-fluorophenyl)-oxo-lambda6-sulfanylidene]amino]-tert-butyl-dimethylsilane | 635311-90-9

• 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: [[[(3R)-3-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butyl]-(4-fluorophenyl)-oxo-lambda6-sulfanylidene]amino]-tert-butyl-dimethylsilane
• 英文别名: [[[(3R)-3-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butyl]-(4-fluorophenyl)-oxo-λ6-sulfanylidene]amino]-tert-butyl-dimethylsilane
• CAS: 635311-90-9
• 化学式: C₄₇H₈₂FNO₃SSi₃
• 分子量: 844.494
• InChiKey: QPODOFSBZFXGGG-IZQBDQCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.88
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [[[(3R)-3-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butyl]-(4-fluorophenyl)-oxo-lambda6-sulfanylidene]amino]-tert-butyl-dimethylsilane 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以26%的产率得到(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-4-[(4-fluorophenyl)sulfonimidoyl]butan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-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：

  1-氟-4-(甲基亚磺酰基)苯 在 吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 sodium azide 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 17.0h， 生成 [[[(3R)-3-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]butyl]-(4-fluorophenyl)-oxo-lambda6-sulfanylidene]amino]-tert-butyl-dimethylsilane
  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+