(4-Bromophenyl)-[4-phenyl-5-(piperidine-1-carbonyl)-2,3-dihydropyrrol-1-yl]methanone | 1323140-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4-Bromophenyl)-[4-phenyl-5-(piperidine-1-carbonyl)-2,3-dihydropyrrol-1-yl]methanone
• CAS: 1323140-90-4
• 化学式: C₂₃H₂₃BrN₂O₂
• 分子量: 439.352
• InChiKey: QZRWYIWDULHNGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-Bromophenyl)-[4-phenyl-5-(piperidine-1-carbonyl)-2,3-dihydropyrrol-1-yl]methanone 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 (4-Bromophenyl)-[3-phenyl-2-(piperidine-1-carbonyl)pyrrolidin-1-yl]methanone
  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
• 作为产物：
  描述：

  1,3-diethyl 2-[(4-bromophenyl)formamido]propanedioate 在 吡啶 、 三乙基硅烷 、 水 、 sodium ethanolate 、 copper diacetate 、 lead(IV) tetraacetate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4-Bromophenyl)-[4-phenyl-5-(piperidine-1-carbonyl)-2,3-dihydropyrrol-1-yl]methanone
  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.