4,5-Diphenylpyrrolo(Spiro[2.3']Oxindole)Spiro[3.2']Cycloheptanone | 1213777-12-8

• 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: 4,5-Diphenylpyrrolo(Spiro[2.3']Oxindole)Spiro[3.2']Cycloheptanone
• CAS: 1213777-12-8
• 化学式: C₂₉H₂₈N₂O₂
• 分子量: 436.554
• InChiKey: QKIBAWPZFYWVCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  左旋苯甘氨酸 、 靛红 、 环庚酮 以 甲醇 、 水 为溶剂， 反应 24.0h， 以32%的产率得到4,5-Diphenylpyrrolo(Spiro[2.3']Oxindole)Spiro[3.2']Cycloheptanone
  参考文献：
  名称：

  Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines

  摘要：

  One-pot three-component domino reactions of cyclic mono ketones, isatin and sarcosine/phenylglycine furnishing highly functionalised dispiropyrrolidines in moderate yields are described. The reaction when performed with cyclic amino acid, proline resulted in the dimerization of azomethine ylides. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among thirty eight compounds screened, 1-methyl-pyrrolo(spiro[2.3']-5-bromooxindole)spiro[3.2"]-1"- nitrosotetrahydro-4"(1H)-pyridinone (4t) was found to be the most active with MIC of 1.98 mu M against MTB and was 3.86 and 25.64 times more potent than the standard first line TB drugs, ethambutol and pyrazinamide respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.044

文献信息

• Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines
  作者：Raju Suresh Kumar、Stephen Michael Rajesh、Subbu Perumal、Debjani Banerjee、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.09.044

  日期：2010.1

  One-pot three-component domino reactions of cyclic mono ketones, isatin and sarcosine/phenylglycine furnishing highly functionalised dispiropyrrolidines in moderate yields are described. The reaction when performed with cyclic amino acid, proline resulted in the dimerization of azomethine ylides. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among thirty eight compounds screened, 1-methyl-pyrrolo(spiro[2.3']-5-bromooxindole)spiro[3.2"]-1"- nitrosotetrahydro-4"(1H)-pyridinone (4t) was found to be the most active with MIC of 1.98 mu M against MTB and was 3.86 and 25.64 times more potent than the standard first line TB drugs, ethambutol and pyrazinamide respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.