spiro(5-methoxy-2H-benzimidazole-2-cyclopentane) 1,3-dioxide | 1004980-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: spiro(5-methoxy-2H-benzimidazole-2-cyclopentane) 1,3-dioxide
• 英文别名: 5-Methoxy-3-oxidospiro[benzimidazol-1-ium-2,1'-cyclopentane] 1-oxide
• CAS: 1004980-65-7
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: FVABMGBFFIXUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基苯并呋喃 3-氧化物 、 硝基环戊烷 在 哌啶 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到spiro(5-methoxy-2H-benzimidazole-2-cyclopentane) 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.