N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocycloprop[f]isoindol-2-(1H)-yl)-2-((1H-benzo[d]imidazol-1-yl)methanone)ethyl | 1246958-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocycloprop[f]isoindol-2-(1H)-yl)-2-((1H-benzo[d]imidazol-1-yl)methanone)ethyl
• 英文别名: (1S,2S,6R,7R,8R,10S)-4-[3-(benzimidazol-1-yl)-3-oxopropyl]-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione
• CAS: 1246958-28-0
• 化学式: C₂₁H₁₉N₃O₃
• 分子量: 361.4
• InChiKey: NLRDWJJCYOHFLS-GCJSYMKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯并咪唑 、 3-[(1S,2S,6R,7R,8R,10S)-3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl]propanoic acid 在 N,N-二异丙基乙二胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocycloprop[f]isoindol-2-(1H)-yl)-2-((1H-benzo[d]imidazol-1-yl)methanone)ethyl
  参考文献：
  名称：

  Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents

  摘要：

  By modifying the chemical structure of anti-orthopoxvirus compound ST-246, we designed and synthesized a series of tricyclononene carboxamide derivatives and tested their anti-HIV-1 activity and cytotoxicity. We found that benzoimidazol-containing compound 7g was highly effective in inhibiting HIV-1 R5 infection with an IC50 value of 0.41 mu M and a selectivity index of 292, but it exhibited no significant inhibitory activity on HIV-1 reverse transcriptase, integrase and protease. CoMFA was used to analyze structure-activity relationships with good predictive power (r(2) = 0.921; q(2) = 0.582). Moreover, the CoMFA model showed that the length of the molecule, the amide, and the amine moieties all played crucial roles in anti-HIV activity. These results suggest that 7g may serve as a lead for the development of novel anti-HIV-1 therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.070

文献信息

• Tricyclononene carboxamide derivatives as novel anti-HIV-1 agents
  作者：Ming-xin Dong、Jian Zhang、Xu-qing Peng、Hong Lu、Liu-hong Yun、Shibo Jiang、Qiu-yun Dai

  DOI：10.1016/j.ejmech.2010.05.070

  日期：2010.9

  By modifying the chemical structure of anti-orthopoxvirus compound ST-246, we designed and synthesized a series of tricyclononene carboxamide derivatives and tested their anti-HIV-1 activity and cytotoxicity. We found that benzoimidazol-containing compound 7g was highly effective in inhibiting HIV-1 R5 infection with an IC50 value of 0.41 mu M and a selectivity index of 292, but it exhibited no significant inhibitory activity on HIV-1 reverse transcriptase, integrase and protease. CoMFA was used to analyze structure-activity relationships with good predictive power (r(2) = 0.921; q(2) = 0.582). Moreover, the CoMFA model showed that the length of the molecule, the amide, and the amine moieties all played crucial roles in anti-HIV activity. These results suggest that 7g may serve as a lead for the development of novel anti-HIV-1 therapies. (C) 2010 Elsevier Masson SAS. All rights reserved.