3,5-bis[(E)-(2-bromophenyl)methylidene]-1-[(R)-1-phenylethyl]tetrahydro-4(1H)-pyridinone | 1245653-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,5-bis[(E)-(2-bromophenyl)methylidene]-1-[(R)-1-phenylethyl]tetrahydro-4(1H)-pyridinone
• 英文别名: (3E,5E)-3,5-bis[(2-bromophenyl)methylidene]-1-[(1R)-1-phenylethyl]piperidin-4-one
• CAS: 1245653-62-6
• 化学式: C₂₇H₂₃Br₂NO
• 分子量: 537.294
• InChiKey: IXLTVKZVWZAYER-PFVGGDPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-bis[(E)-(2-bromophenyl)methylidene]-1-[(R)-1-phenylethyl]tetrahydro-4(1H)-pyridinone 、 benzohydroximoyl chloride 在 三乙胺 作用下， 以 苯 为溶剂， 以25%的产率得到(5S,6S,10R)-10-(2-bromophenyl)-14-[(E)-1-(2-bromophenyl)methylidene]-3,9-diphenyl-12-(1-phenylethyl)-1,4,7-trioxa-2,8,12-triazadispiro[4.0.4.4]tetradeca-2,8-diene
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of nitrile oxides to (R)-1-(1-phenylethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: synthesis and antimycobacterial evaluation of novel enantiomerically pure di- and trispiroheterocycles

  摘要：

  Enantiomerically pure (R)-(1-phenylethyl)-3,5-bisRE)-arylmethylidenejtetrahydro-4(1H)-pyridinones were synthesized for the first time, and their 1,3-dipolar cycloaddition with nitrite oxides affording diand trispiroheterocycles regio- and stereoselectively in moderate yields was investigated. These compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug-resistant M. tuberculosis (MDR-TB). Among the compounds screened, the dispiroheterocycle, namely, (5R,6R,105)3,9-bis(4-chloropheny1)-10-(2,4-dichloropheny1)-14-[(E)-(2,4-dichlorophenyl)methylidenel-12-1(R)-1- phenylethyl]-1,4,7-trioxa-2,8,12-tri-azadispiro14.0.4.41tetradeca-2,8-diene 5m was found to possess the maximum activity with MIC of 0.49 p.M against MTB, being 9.6 and 15.6 times more potent than ciprofloxacin and ethambutol, respectively. Against MDR-TB, 5m displayed maximum activity with an MIC of 0.49 uM, with it thus being more active than rifampicin, isoniazid, ciprofloxacin and ethambutol by 7.8, 23, 77 and 124 times, respectively. 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.054
• 作为产物：
  描述：

  (R)-1-(1-phenylethyl)piperidin-4-one 、 邻溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以84%的产率得到3,5-bis[(E)-(2-bromophenyl)methylidene]-1-[(R)-1-phenylethyl]tetrahydro-4(1H)-pyridinone
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of nitrile oxides to (R)-1-(1-phenylethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: synthesis and antimycobacterial evaluation of novel enantiomerically pure di- and trispiroheterocycles

  摘要：

  Enantiomerically pure (R)-(1-phenylethyl)-3,5-bisRE)-arylmethylidenejtetrahydro-4(1H)-pyridinones were synthesized for the first time, and their 1,3-dipolar cycloaddition with nitrite oxides affording diand trispiroheterocycles regio- and stereoselectively in moderate yields was investigated. These compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug-resistant M. tuberculosis (MDR-TB). Among the compounds screened, the dispiroheterocycle, namely, (5R,6R,105)3,9-bis(4-chloropheny1)-10-(2,4-dichloropheny1)-14-[(E)-(2,4-dichlorophenyl)methylidenel-12-1(R)-1- phenylethyl]-1,4,7-trioxa-2,8,12-tri-azadispiro14.0.4.41tetradeca-2,8-diene 5m was found to possess the maximum activity with MIC of 0.49 p.M against MTB, being 9.6 and 15.6 times more potent than ciprofloxacin and ethambutol, respectively. Against MDR-TB, 5m displayed maximum activity with an MIC of 0.49 uM, with it thus being more active than rifampicin, isoniazid, ciprofloxacin and ethambutol by 7.8, 23, 77 and 124 times, respectively. 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.054

文献信息

• 1,3-Dipolar cycloaddition of nitrile oxides to (R)-1-(1-phenylethyl)-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones: synthesis and antimycobacterial evaluation of novel enantiomerically pure di- and trispiroheterocycles
  作者：Raju Suresh Kumar、Stephen Michael Rajesh、Subbu Perumal、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.tetasy.2010.03.054

  日期：2010.6

  Enantiomerically pure (R)-(1-phenylethyl)-3,5-bisRE)-arylmethylidenejtetrahydro-4(1H)-pyridinones were synthesized for the first time, and their 1,3-dipolar cycloaddition with nitrite oxides affording diand trispiroheterocycles regio- and stereoselectively in moderate yields was investigated. These compounds were evaluated against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug-resistant M. tuberculosis (MDR-TB). Among the compounds screened, the dispiroheterocycle, namely, (5R,6R,105)3,9-bis(4-chloropheny1)-10-(2,4-dichloropheny1)-14-[(E)-(2,4-dichlorophenyl)methylidenel-12-1(R)-1- phenylethyl]-1,4,7-trioxa-2,8,12-tri-azadispiro14.0.4.41tetradeca-2,8-diene 5m was found to possess the maximum activity with MIC of 0.49 p.M against MTB, being 9.6 and 15.6 times more potent than ciprofloxacin and ethambutol, respectively. Against MDR-TB, 5m displayed maximum activity with an MIC of 0.49 uM, with it thus being more active than rifampicin, isoniazid, ciprofloxacin and ethambutol by 7.8, 23, 77 and 124 times, respectively. 2010 Elsevier Ltd. All rights reserved.