methyl 4-[(N-benzylanilino)methyl]benzoate | 1297654-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-[(N-benzylanilino)methyl]benzoate
• CAS: 1297654-35-3
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: CHMRVGHYPRRQAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-[(N-benzylanilino)methyl]benzoate 在 草酰氯 、 水 、 N,N-二甲基甲酰胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (2R)-2-[[4-[(N-benzylanilino)methyl]benzoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Discovery of novel PTP1B inhibitors via pharmacophore-oriented scaffold hopping from Ertiprotafib

  摘要：

  An integrated molecular design strategy combining pharmacophore recognition and scaffold hopping was exploited to discover novel PTP1B inhibitors based on the known PTP1B inhibitor Ertiprotafib. A composite pharmacophore model was proposed from the interaction mode of Ertiprotafib, and 21 diverse molecules from five distinct structural classes were designed and synthesized accordingly. New compounds with considerable inhibition against PTP1B were identified from each series, and the most active compound 3a showed IC50 value of 1.3 mu mol L-1 against human recombinant PTP1B. Docking study indicated that the new inhibitors assumed binding modes similar to that of Ertiprotafib. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.002
• 作为产物：
  描述：

  苯甲基苯胺 、 4-溴甲基苯甲酸甲酯 在 N,N-二异丙基乙二胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4-[(N-benzylanilino)methyl]benzoate
  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

• Discovery of novel PTP1B inhibitors via pharmacophore-oriented scaffold hopping from Ertiprotafib
  作者：Jun-Zheng Liu、Shu-En Zhang、Feilin Nie、Ying Yang、Yan-Bo Tang、Wenwen Yin、Jin-Ying Tian、Fei Ye、Zhiyan Xiao

  DOI：10.1016/j.bmcl.2013.10.002

  日期：2013.12

  An integrated molecular design strategy combining pharmacophore recognition and scaffold hopping was exploited to discover novel PTP1B inhibitors based on the known PTP1B inhibitor Ertiprotafib. A composite pharmacophore model was proposed from the interaction mode of Ertiprotafib, and 21 diverse molecules from five distinct structural classes were designed and synthesized accordingly. New compounds with considerable inhibition against PTP1B were identified from each series, and the most active compound 3a showed IC50 value of 1.3 mu mol L-1 against human recombinant PTP1B. Docking study indicated that the new inhibitors assumed binding modes similar to that of Ertiprotafib. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.