4-[[(1R,2S,4R,7R,10S)-4-ethyl-15,15-difluoro-5,5,12-trioxo-17-oxa-5lambda6-thia-6-azatetracyclo[8.8.0.02,7.011,16]octadeca-11(16),13-dien-10-yl]sulfonyl]benzonitrile | 1417802-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[[(1R,2S,4R,7R,10S)-4-ethyl-15,15-difluoro-5,5,12-trioxo-17-oxa-5lambda6-thia-6-azatetracyclo[8.8.0.02,7.011,16]octadeca-11(16),13-dien-10-yl]sulfonyl]benzonitrile
• 英文别名: 4-[[(1R,2S,4R,7R,10S)-4-ethyl-15,15-difluoro-5,5,12-trioxo-17-oxa-5λ6-thia-6-azatetracyclo[8.8.0.02,7.011,16]octadeca-11(16),13-dien-10-yl]sulfonyl]benzonitrile
• CAS: 1417802-80-2
• 化学式: C₂₄H₂₄F₂N₂O₆S₂
• 分子量: 538.593
• InChiKey: UTKNCPXIXJKKPY-INEWRBNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-[[(1R,2S,4R,7R,10S)-4-ethyl-12,15-difluoro-5,5-dioxo-17-oxa-5lambda6-thia-6-azatetracyclo[8.8.0.02,7.011,16]octadeca-11,13,15-trien-10-yl]sulfonyl]benzonitrile 在 Selectfluor 、 水 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 4-[[(1R,2S,4R,7R,10S)-4-ethyl-15,15-difluoro-5,5,12-trioxo-17-oxa-5lambda6-thia-6-azatetracyclo[8.8.0.02,7.011,16]octadeca-11(16),13-dien-10-yl]sulfonyl]benzonitrile
  参考文献：
  名称：

  A-ring modification of SCH 900229 and related chromene sulfone γ-secretase inhibitors

  摘要：

  Attempts to block metabolism by incorporating a 9-fluoro substituent at the A-ring of compound 1 (SCH 900229) using electrophilic Selectfluor (TM) led to an unexpected oxidation of the A-ring to give difluoroquinone analog 1a. Oxidation of other related chromene gamma-secretase inhibitors 2-8 resulted in similar difluoroquinone analogs 2a-8a, respectively. These quinone products exhibited comparable in vitro potency in a gamma-scretase membrane assay, but were several fold less potent in a cell-based assay in lowering A beta 40-42, compared to their parent compounds. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.054