4-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido<1,2-a>benzimidazol-2-one

• 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: 4-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido<1,2-a>benzimidazol-2-one
• 英文别名: 4-(4-methoxyphenyl)-4,10-dihydro-3H-pyrimido[1,2-a]benzimidazol-2-one
• 化学式: C₁₇H₁₅N₃O₂
• 分子量: 293.325
• InChiKey: NRSWDKSPCKHVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基苯并咪唑 、 4-甲氧基肉桂酸 以75%的产率得到4-(4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido<1,2-a>benzimidazol-2-one
  参考文献：
  名称：

  Immunotropic Properties of 2-Aminobenzimidazole Derivatives in Cultures of Human Peripheral Blood Cells, Part 5

  摘要：

  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.

  DOI：

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

文献信息

• ——
  作者：V. V. Lipson、V. D. Orlov、S. M. Desenko、S. V. Shishkina、O. V. Shishkin、M. G. Shirobokova

  DOI：10.1023/a:1002777714158

  日期：——
• 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.