(E/Z)-2,2-dimethyl-5-[(3,4-methylendioxyphenyl)ethenyl]-2H-benzimidazole 1,3-dioxide

• 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: (E/Z)-2,2-dimethyl-5-[(3,4-methylendioxyphenyl)ethenyl]-2H-benzimidazole 1,3-dioxide
• 英文别名: 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-2,2-dimethyl-3-oxidobenzimidazol-1-ium 1-oxide
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: QHXQDQPWNZHUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-硝基丙烷 、 5-[2-(1,3-benzodioxol-5-yl)ethenyl]-3-oxido-2,1,3-benzoxadiazol-3-ium 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 以19%的产率得到(E/Z)-2,2-dimethyl-5-[(3,4-methylendioxyphenyl)ethenyl]-2H-benzimidazole 1,3-dioxide
  参考文献：
  名称：

  Second generation of 2H-benzimidazole 1,3-dioxide derivatives as anti-trypanosomatid agents: Synthesis, biological evaluation, and mode of action studies

  摘要：

  Exploring the influence of different substitution patterns of 2H-benzimidazole 1,3-dioxide derivatives (BzNO) we prepared fifteen new derivatives. Initially the BzNO were tested against Trypanosoma cruzi Tulahuen 2 strain epimastigote form rendering very potent anti-T. cruzi agents. Moreover, the BzNO were able to inhibit the growth of virulent and resistant to Benznidazole strains (CL Brener clone, Colombiana, and Y strains) and to Leishmania braziliensis. Interestingly, BzNO exhibited very high selectivity index and particularly the spiro-BzNO 13 provokes an important diminution of amastigotes in Vero cells. Besides, it was found a diminution of acetate and glycine as excreted metabolites but without increase of parasite glucose uptake indicating that the glycosome is probably not involucrate in the 2H-benzimidazole 1,3-dioxides mechanism of action. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.014

文献信息

• Second generation of 2H-benzimidazole 1,3-dioxide derivatives as anti-trypanosomatid agents: Synthesis, biological evaluation, and mode of action studies
  作者：Mariana Boiani、Lucía Boiani、Alicia Merlino、Paola Hernández、Agustina Chidichimo、Juan J. Cazzulo、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.ejmech.2009.06.014

  日期：2009.11

  Exploring the influence of different substitution patterns of 2H-benzimidazole 1,3-dioxide derivatives (BzNO) we prepared fifteen new derivatives. Initially the BzNO were tested against Trypanosoma cruzi Tulahuen 2 strain epimastigote form rendering very potent anti-T. cruzi agents. Moreover, the BzNO were able to inhibit the growth of virulent and resistant to Benznidazole strains (CL Brener clone, Colombiana, and Y strains) and to Leishmania braziliensis. Interestingly, BzNO exhibited very high selectivity index and particularly the spiro-BzNO 13 provokes an important diminution of amastigotes in Vero cells. Besides, it was found a diminution of acetate and glycine as excreted metabolites but without increase of parasite glucose uptake indicating that the glycosome is probably not involucrate in the 2H-benzimidazole 1,3-dioxides mechanism of action. (C) 2009 Elsevier Masson SAS. All rights reserved.