N-methyl-spiro[2.3’’]oxindole-spiro[3.3’]benzofuran-2’-one-4-(4-methoxyphenyl)pyrrolidine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-spiro[2.3’’]oxindole-spiro[3.3’]benzofuran-2’-one-4-(4-methoxyphenyl)pyrrolidine
• 化学式: C₂₆H₂₂N₂O₄
• 分子量: 426.472
• InChiKey: JRVJWBIEGLGATJ-GKBBYZSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  肌氨酸 、 3-(4-methoxybenzylidene)benzofuran-2(3H)-one 、 靛红 以 甲醇 为溶剂， 反应 1.0h， 以73%的产率得到N-methyl-spiro[2.3’’]oxindole-spiro[3.3’]benzofuran-2’-one-4-(4-methoxyphenyl)pyrrolidine
  参考文献：
  名称：

  Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents

  摘要：

  With the aim to develop new potent antitubercular agents, a series of novel dispirooxindolopyrrolidines and dispirooxindolopyrrolothiazoles have been synthesized via a three-component 1,3-dipolar cycloaddition of (Z)-3-arylidenebenzofuran-2-ones, substituted isatin derivatives and alpha-aminoacids. The stereochemistry of the spiroadducts has been confirmed by an X-ray diffraction analysis. All the target heterocycles were evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain and the most active compounds were subjected to cytotoxicity studies against (RAW 264.7) cell lines. Among them, twelve compounds showed potent anti-tubercular activity with MIC ranging from 1.56 to 6.25 mu g/mL. In particular dispirooxindolopyrrolothiazole derivatives 5c and 5f were found to be the most active (MIC of 1.56 mu g/mL) with a good safety profile (27.53% and 20.74% at 50 mu M, respectively). This is the first report demonstrating the benzofuranone oxindole hybrids as potential antimycobacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.069

文献信息

• Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents
  作者：Chourouk Mhiri、Sarra Boudriga、Moheddine Askri、Michael Knorr、Dharmarajan Sriram、Perumal Yogeeswari、Frédéric Nana、Christopher Golz、Carsten Strohmann

  DOI：10.1016/j.bmcl.2015.07.069

  日期：2015.10

  With the aim to develop new potent antitubercular agents, a series of novel dispirooxindolopyrrolidines and dispirooxindolopyrrolothiazoles have been synthesized via a three-component 1,3-dipolar cycloaddition of (Z)-3-arylidenebenzofuran-2-ones, substituted isatin derivatives and alpha-aminoacids. The stereochemistry of the spiroadducts has been confirmed by an X-ray diffraction analysis. All the target heterocycles were evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain and the most active compounds were subjected to cytotoxicity studies against (RAW 264.7) cell lines. Among them, twelve compounds showed potent anti-tubercular activity with MIC ranging from 1.56 to 6.25 mu g/mL. In particular dispirooxindolopyrrolothiazole derivatives 5c and 5f were found to be the most active (MIC of 1.56 mu g/mL) with a good safety profile (27.53% and 20.74% at 50 mu M, respectively). This is the first report demonstrating the benzofuranone oxindole hybrids as potential antimycobacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.