(3R,4R,5S)-2,3-diphenyl-7-[(R)-1-phenylethyl]-4-(2-thienyl)-1-oxa-2,7-diazaspiro[4.5]decan-10-one | 1213240-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3R,4R,5S)-2,3-diphenyl-7-[(R)-1-phenylethyl]-4-(2-thienyl)-1-oxa-2,7-diazaspiro[4.5]decan-10-one
• CAS: 1213240-58-4
• 化学式: C₃₁H₃₀N₂O₂S
• 分子量: 494.657
• InChiKey: NIHUXOYPODONJS-UEHSUQEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (R,E)-1-(1-phenylethyl)-3-(thiophen-2-ylmethylene)piperidin-4-one 、 N-(benzylidene)aniline N-oxide 以 甲苯 为溶剂， 反应 16.0h， 以30%的产率得到(3S,4S,5R)-2,3-diphenyl-7-[(R)-1-phenylethyl]-4-(2-thienyl)-1-oxa-2,7-diazaspiro[4.5]decan-10-one
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of C-aryl-N-phenylnitrones to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: Synthesis and antimycobacterial evaluation of enantiomerically pure spiroisoxazolidines

  摘要：

  A series of novel enantiomerically pure spiroisoxazolidines were synthesized regioselectively by the 1,3-dipolar cycloaddition of C-aryl-N-phenylnitrones to (R)-1-(1-phenylethyl)-3-[(E)-arylmethylidenejtetrahydro-4(1H)-pyridinones. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among the twenty two compounds screened, (3S,4S,5R)-3,4-di(4-methylphenyl)-2-phenyl-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]decan-10-one (3e) was found to possess the maximum activity with MIC of 3.02 mu M, being 2.5 times more potent than the first-line anti-TB drug ethambutol. For comparison, a series of ten enantiomerically pure spirooxazolines were also screened, among which (4R,5S)-3,4-bis(4-chlorophenyl)-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one and (4R,5S)-4-(2-chlorophenyl)-3-(4-chlorophenyl)-7-[(R)-1-phenylethyl]-1-oxa-2,7-diazaspiro[4.5]dec-2-en-10-one were found to display maximum activity with MIC of 3.25 mu M. (C) 2009 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.09.034