N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocycloprop[f]isoindol-2-(1H)-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide | 1246958-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 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)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide
• 英文别名: 4-(2,5-dimethylpyrrol-1-yl)-N-[(1S,2S,6R,7R,8R,10S)-3,5-dioxo-4-azatetracyclo[5.3.2.02,6.08,10]dodec-11-en-4-yl]benzamide
• CAS: 1246958-21-3
• 化学式: C₂₄H₂₃N₃O₃
• 分子量: 401.465
• InChiKey: FJOBJIMDJVLVLO-QUTUUGMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(2,5-二甲基-吡-1-基)苯甲酰肼 、 cycloheptatriene-maleic anhydride adduct 在 N,N-二异丙基乙二胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-(3,3a,4,4a,5,5a,6,6a-octahydro-1,3-dioxo-4,6-ethanocycloprop[f]isoindol-2-(1H)-yl)-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzamide
  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.