N-[3-(2-chloro-acetylamino)-phenyl]-benzamide | 1233188-83-4

• 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: N-[3-(2-chloro-acetylamino)-phenyl]-benzamide
• 英文别名: N-{3-[(chloroacetyl)amino]phenyl}benzamide；N-[3-[(2-chloroacetyl)amino]phenyl]benzamide
• CAS: 1233188-83-4
• 化学式: C₁₅H₁₃ClN₂O₂
• mdl: MFCD20492081
• 分子量: 288.733
• InChiKey: DWNHTHNQFOAYLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[3-(2-chloro-acetylamino)-phenyl]-benzamide 、 2-(4-phenylpiperazine-1-carbonothioyl)malononitrile 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以84%的产率得到3-amino-N-(3-benzamidophenyl)-4-cyano-5-(4-phenylpiperazin-1-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  有效合成新的3-氨基-4-氰基噻吩衍生物

  摘要：

  描述了对先前报道的合成四取代噻吩的合成途径的有效且原子经济的修饰。先前公开的合成方法涉及从烯酮二硫缩醛和适当的仲胺开始的一锅法，然后与Na 2 S和苯甲酰溴反应。然而，释放的甲烷硫醇盐副产物与烯硫醇盐中间体争夺苯甲酰溴，这降低了收率，并且必须使用两个摩尔当量的α-卤代酮试剂以增加目标噻吩产物的收率。在目前的工作中，所提出的修饰包括分离中间体烯硫醇衍生物，从而减少了α的数量。-卤代酮至一摩尔当量。此外，优化反应条件以获得最佳的碱/溶剂组合以提高目标衍生物的产率。按照我们改进的方法，合成并分离了三个系列的新型3-氨基-4-氰基噻吩衍生物，并具有高收率和高纯度。

  DOI：

  10.1007/s11696-020-01070-z
• 作为产物：
  描述：

  氯乙酰氯 、 N-(3-氨基苯基)苯甲酰胺 在 三乙胺 作用下， 以 丙酮 为溶剂， 以69%的产率得到N-[3-(2-chloro-acetylamino)-phenyl]-benzamide
  参考文献：
  名称：

  Elaborate ligand-based pharmacophore exploration and QSAR analysis guide the synthesis of novel pyridinium-based potent β-secretase inhibitory leads

  摘要：

  beta-Secretase (BACE) inhibitors have potential as anti-Alzheimer's disease treatments prompting us to explore the pharmacophoric space of 129 known BACE inhibitors. QSAR analysis was employed to select optimal combination of pharmacophoric models and 2D physicochemical descriptors capable of explaining bioactivity variation (r(2) = 0.88, F = 60.48, r(LOO)(2) = 0.85, r(PRESS)(2) against 25 external test inhibitors = 0.71). We were obliged to use ligand efficiency as the response variable because the logarithmic transformation of bioactivities failed to access self-consistent QSAR models. Three pharmacophoric models emerged in the successful QSAR equation suggesting at least three binding modes accessible to ligands within BACE binding pocket. QSAR equation and pharmacophoric models were validated through ROC curves and were employed to guide synthesis of novel pyridinium-based BACE inhibitors. The best inhibitor illustrated an IC50 value of 1.0 mu M against BACE. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.043

文献信息

• Elaborate ligand-based pharmacophore exploration and QSAR analysis guide the synthesis of novel pyridinium-based potent β-secretase inhibitory leads
  作者：Afaf Al-Nadaf、Ghassan Abu Sheikha、Mutasem O. Taha

  DOI：10.1016/j.bmc.2010.03.043

  日期：2010.5

  beta-Secretase (BACE) inhibitors have potential as anti-Alzheimer's disease treatments prompting us to explore the pharmacophoric space of 129 known BACE inhibitors. QSAR analysis was employed to select optimal combination of pharmacophoric models and 2D physicochemical descriptors capable of explaining bioactivity variation (r(2) = 0.88, F = 60.48, r(LOO)(2) = 0.85, r(PRESS)(2) against 25 external test inhibitors = 0.71). We were obliged to use ligand efficiency as the response variable because the logarithmic transformation of bioactivities failed to access self-consistent QSAR models. Three pharmacophoric models emerged in the successful QSAR equation suggesting at least three binding modes accessible to ligands within BACE binding pocket. QSAR equation and pharmacophoric models were validated through ROC curves and were employed to guide synthesis of novel pyridinium-based BACE inhibitors. The best inhibitor illustrated an IC50 value of 1.0 mu M against BACE. (c) 2010 Elsevier Ltd. All rights reserved.
• Efficient synthesis of new 3-amino-4-cyanothiophene derivatives
  作者：Salwa E. M. El-Meligie、Nadia A. Khalil、Hala B. El-Nassan、Ahmed A. M. Ibraheem

  DOI：10.1007/s11696-020-01070-z

  日期：2020.8

  in isolation of the intermediate enethiolate derivative, thereby reducing quantity of the α-haloketone to one molar equivalent. Moreover, the reaction conditions were optimized to attain optimum base/solvent combination to improve the yield of the target derivatives. Following our modified procedure, three series of new 3-amino-4-cyanothiophene derivatives were synthesized and isolated in high yields

  描述了对先前报道的合成四取代噻吩的合成途径的有效且原子经济的修饰。先前公开的合成方法涉及从烯酮二硫缩醛和适当的仲胺开始的一锅法，然后与Na 2 S和苯甲酰溴反应。然而，释放的甲烷硫醇盐副产物与烯硫醇盐中间体争夺苯甲酰溴，这降低了收率，并且必须使用两个摩尔当量的α-卤代酮试剂以增加目标噻吩产物的收率。在目前的工作中，所提出的修饰包括分离中间体烯硫醇衍生物，从而减少了α的数量。-卤代酮至一摩尔当量。此外，优化反应条件以获得最佳的碱/溶剂组合以提高目标衍生物的产率。按照我们改进的方法，合成并分离了三个系列的新型3-氨基-4-氰基噻吩衍生物，并具有高收率和高纯度。