2-[3-(4-methoxyphenyl)acrylamido]benzimidazole

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[3-(4-methoxyphenyl)acrylamido]benzimidazole
• 英文别名: 2-(4-methoxycinnamoylamino)benzimidazole；2-[3-(4-Methoxyphenyl)acrylamido]-benzimidazole；N-(1H-benzimidazol-2-yl)-3-(4-methoxyphenyl)prop-2-enamide
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: KJLLFDIDFCZMLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 吡啶 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 为溶剂， 反应 33.0h， 生成 2-[3-(4-methoxyphenyl)acrylamido]benzimidazole
  参考文献：
  名称：

  Design, synthesis, and PASS-assisted evaluation of novel 2-substituted benzimidazole derivatives as potent anthelmintics

  摘要：

  A series of novel 2-substituted benzimidazole analogs has been designed and synthesized by connecting the benzimidazole nucleus with variedly substituted chalcone moieties through an amino linker. The designed analogs were predicted for their biological activity profile through the computer software PASS. The compounds were predicted to have potent anthelmintic activity. These were synthesized and the activity of each compound was evaluated experimentally at the concentrations of 0.1, 0.2, and 0.5 % in terms of mortality time and paralysis time for the helminthes. The experimentally observed activity was found to comply with the PASS predicted activity. All compounds showed dose-dependent activities. The compounds with an electron releasing group at the para position on phenyl ring in the chalcone moiety (8 and 9) were the most active in comparison to those bearing electron withdrawing groups. The corresponding ortho analogs (4 and 5) also revealed good paralytic and lethal activities. The higher activities of 8 and 9 may be attributed to the favorable electronic interactions of the electron releasing groups present at para position of the phenyl ring. Comparative analysis of the Lipinski's parameters and the activities of the compounds revealed all the compounds to comply with the Lipinski's rule of five. Further an optimum hydrophilicity and total polar surface area in the range of 65-80 of the molecule are required for the potent activity, but Molar refractance is not found to have any significant role in determining the anthelmintic activity.

  DOI：

  10.1007/s00044-013-0856-1

文献信息

• Immunotropic Properties of 2-Aminobenzimidazole Derivatives in Cultures of Human Peripheral Blood Cells, Part 5
  作者：Wanda Nawrocka、Michal Zimecki、Tomasz Kuznicki、Maria Wiktoria Kowalska

  DOI：10.1002/(sici)1521-4184(19993)332:3<85::aid-ardp85>3.0.co;2-s

  日期：1999.3

  The reaction of 2-aminobenzimidazole with selected 4-methoxy-, 2.4-dimethoxy-, 4-chloro-, 4-nitro-, and 2-nitrocinnamic acid under different conditions has been described. Two series of derivatives were obtained: 4-aryl-1,2,3,4-tetrahydropyrimido[1,2-a]-benzimidazol-2-ones (1-3) or substituted amides 4, 5, 7. The following compounds: 4-(p-methoxyphenyl)- (1), 4-(2,4-dimethoxyphenyl)- (2), 4-(p-chlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-2-one (3), amides: 2-(p-nitro-cinnamoylamino)- (4), 2-(p-methoxycinnamoylamino)-benzimidazole (5), and 3-methyl-1,2,3,4-tetrahydropyrimido[ 1,2-a]benzimidazol-2-one (6), recently synthesized, have been selected for further studies. Among the studied compounds, 3 and 4 strongly inhibited PHA-induced proliferation of human lymphocytes and weaker, but significantly, MLC-induced lymphocyte proliferation. 3 and 4 inhibited also LPS- or MLC-induced TNF-alpha production. In addition, TNF-a production, induced by LPS, was inhibited by compounds 1 and 2. Higher activity of 3 and 4 could be associated with the presence in their structures of -Cl and -NO2 substituents as compared with compounds possessing -OCH3 groups. Compounds 3 and 3 were not toxic when administered orally to mice which predisposes them for further investigations with a chance of clinical application.
• Design, synthesis, and PASS-assisted evaluation of novel 2-substituted benzimidazole derivatives as potent anthelmintics
  作者：Kamalpriya Garg、Yogita Bansal、Gulshan Bansal、R. K. Goel

  DOI：10.1007/s00044-013-0856-1

  日期：2014.5

  A series of novel 2-substituted benzimidazole analogs has been designed and synthesized by connecting the benzimidazole nucleus with variedly substituted chalcone moieties through an amino linker. The designed analogs were predicted for their biological activity profile through the computer software PASS. The compounds were predicted to have potent anthelmintic activity. These were synthesized and the activity of each compound was evaluated experimentally at the concentrations of 0.1, 0.2, and 0.5 % in terms of mortality time and paralysis time for the helminthes. The experimentally observed activity was found to comply with the PASS predicted activity. All compounds showed dose-dependent activities. The compounds with an electron releasing group at the para position on phenyl ring in the chalcone moiety (8 and 9) were the most active in comparison to those bearing electron withdrawing groups. The corresponding ortho analogs (4 and 5) also revealed good paralytic and lethal activities. The higher activities of 8 and 9 may be attributed to the favorable electronic interactions of the electron releasing groups present at para position of the phenyl ring. Comparative analysis of the Lipinski's parameters and the activities of the compounds revealed all the compounds to comply with the Lipinski's rule of five. Further an optimum hydrophilicity and total polar surface area in the range of 65-80 of the molecule are required for the potent activity, but Molar refractance is not found to have any significant role in determining the anthelmintic activity.