1-[2-benzoylamino-3-(4-chloro-phenyl)-acryloyl]-piperidine | 52900-48-8

• 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: 1-[2-benzoylamino-3-(4-chloro-phenyl)-acryloyl]-piperidine
• 英文别名: N-[1-(4-chlorophenyl)-3-oxo-3-piperidin-1-ylprop-1-en-2-yl]benzamide
• CAS: 52900-48-8
• 化学式: C₂₁H₂₁ClN₂O₂
• mdl: MFCD02642385
• 分子量: 368.863
• InChiKey: SMJZCZJOXYHZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-benzoylamino-3-(4-chloro-phenyl)-acryloyl]-piperidine 在 氯化亚砜 作用下， 以3%的产率得到(Z)-N-(1-chloro-1-(4-chlorophenyl)-3-oxo-3-(piperidin-1-yl)prop-1-en-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and quantitative structure–activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication

  摘要：

  A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure activity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on OFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (S-theta) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.032
• 作为产物：
  描述：

  苯甲酰氯 在 sodium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 生成 1-[2-benzoylamino-3-(4-chloro-phenyl)-acryloyl]-piperidine
  参考文献：
  名称：

  Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs

  摘要：

  Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t) ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 mu M in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.077

文献信息

• Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs
  作者：Peiyuan Wang、Devan Naduthambi、Ralph T. Mosley、Congrong Niu、Phillip A. Furman、Michael J. Otto、Michael J. Sofia

  DOI：10.1016/j.bmcl.2011.05.077

  日期：2011.8

  Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t) ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 mu M in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and quantitative structure–activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
  作者：Jing Yang、Min Ma、Xue-Ding Wang、Xing-Jun Jiang、Yuan-Yuan Zhang、Wei-Qing Yang、Zi-Cheng Li、Xi-Hong Wang、Bin Yang、Meng-Lin Ma

  DOI：10.1016/j.ejmech.2015.05.032

  日期：2015.6

  A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure activity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on OFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (S-theta) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction. (C) 2015 Elsevier Masson SAS. All rights reserved.