4-(4-fluorophenyl)-5-phenylpyrrole(spiro[2.2'']acenaphthene-1''-one)-spiro[3.3']-5'-(4-chlorophenylmethylidene)-1'-methyltetrahydro-4'(1'H)-pyridinone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-(4-fluorophenyl)-5-phenylpyrrole(spiro[2.2'']acenaphthene-1''-one)-spiro[3.3']-5'-(4-chlorophenylmethylidene)-1'-methyltetrahydro-4'(1'H)-pyridinone
• 化学式: C₃₉H₃₀F₂N₂O₂
• 分子量: 596.676
• InChiKey: HJJDMOLQWCKRJC-XQTRVIIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  45
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3E,5E)-1-methyl-3,5-bis(4-fluorobenzylidene)piperidin-4-one 、 2-氨基-2-苯基乙酸 、 苊醌 以 甲醇 为溶剂， 反应 1.0h， 以98%的产率得到4-(4-fluorophenyl)-5-phenylpyrrole(spiro[2.2'']acenaphthene-1''-one)-spiro[3.3']-5'-(4-chlorophenylmethylidene)-1'-methyltetrahydro-4'(1'H)-pyridinone
  参考文献：
  名称：

  A highly atom economic, chemo-, regio- and stereoselective synthesis, and discovery of spiro-pyrido-pyrrolizines and pyrrolidines as antimycobacterial agents

  摘要：

  The 1,3-dipolar cycloaddition of azomethine ylides derived from acenaphthenequinone and alpha-amino acids viz. proline, phenylglycine and sarcosine to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel spiro-pyrido-pyrrolizines and pyrrolidines chemo-, regio- and stereoselectively in quantitative yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis using agar dilution method. Among the synthesized compounds, spiro-[2.2 '']acenaphthene-1 ''-one-spiro [3.3']-5'-(2-chlorophenylmethylidene)-1'-methyltetrahydro-4'(1H)-pyridinone-4-(2-chlorophenyl)hexahydro-1H-pyrrolizine (3e) was found to be the most active with a minimum inhibitory concentration (MIC) of 0.4 mu g/mL against MTB and MDR-TB. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.072

文献信息

• A highly atom economic, chemo-, regio- and stereoselective synthesis, and discovery of spiro-pyrido-pyrrolizines and pyrrolidines as antimycobacterial agents
  作者：Raju Ranjith Kumar、Subbu Perumal、Palaniappan Senthilkumar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.tet.2008.01.072

  日期：2008.3

  The 1,3-dipolar cycloaddition of azomethine ylides derived from acenaphthenequinone and alpha-amino acids viz. proline, phenylglycine and sarcosine to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel spiro-pyrido-pyrrolizines and pyrrolidines chemo-, regio- and stereoselectively in quantitative yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis using agar dilution method. Among the synthesized compounds, spiro-[2.2 '']acenaphthene-1 ''-one-spiro [3.3']-5'-(2-chlorophenylmethylidene)-1'-methyltetrahydro-4'(1H)-pyridinone-4-(2-chlorophenyl)hexahydro-1H-pyrrolizine (3e) was found to be the most active with a minimum inhibitory concentration (MIC) of 0.4 mu g/mL against MTB and MDR-TB. (C) 2008 Elsevier Ltd. All rights reserved.