ethyl N-[(1R)-2-[(2S)-2-[(4-bromophenyl)carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate | 1219632-35-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-[(1R)-2-[(2S)-2-[(4-bromophenyl)carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate
• CAS: 1219632-35-5
• 化学式: C₂₂H₂₄BrN₃O₄
• 分子量: 474.354
• InChiKey: HSUPCBUIBGXIOK-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-[(1R)-2-[(2S)-2-[(4-bromophenyl)carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate 、 双(三甲基锡)乙炔 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 diethyl (1,2-ethynediylbis(4,1-phenylenecarbamoyl(2S)-2,1-pyrrolidinediyl((1R)-2-oxo-1-phenyl-2,1-ethanediyl)))biscarbamate
  参考文献：
  名称：

  HCV NS5A replication complex inhibitors. Part 5: Discovery of potent and pan-genotypic glycinamide cap derivatives

  摘要：

  The isoquinolinamide series of HCV NS5A inhibitors exemplified by compounds 2b and 2c provided the first dual genotype-1a/1b (GT-1a/1b) inhibitor class that demonstrated a significant improvement in potency toward GT-1a replicons compared to that of the initial program lead, stilbene 2a. Structure-activity relationship (SAR) studies that uncovered an alternate phenylglycine-based cap series that exhibit further improvements in virology profile, along with some insights into the pharmacophoric elements associated with the GT-1a potency, are described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.040
• 作为产物：
  描述：

  (S)-N-(4-bromophenyl)pyrrolidine-2-carboxamide 在 盐酸 、 三乙胺 、 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-) 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl N-[(1R)-2-[(2S)-2-[(4-bromophenyl)carbamoyl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate
  参考文献：
  名称：

  HCV NS5A replication complex inhibitors. Part 5: Discovery of potent and pan-genotypic glycinamide cap derivatives

  摘要：

  The isoquinolinamide series of HCV NS5A inhibitors exemplified by compounds 2b and 2c provided the first dual genotype-1a/1b (GT-1a/1b) inhibitor class that demonstrated a significant improvement in potency toward GT-1a replicons compared to that of the initial program lead, stilbene 2a. Structure-activity relationship (SAR) studies that uncovered an alternate phenylglycine-based cap series that exhibit further improvements in virology profile, along with some insights into the pharmacophoric elements associated with the GT-1a potency, are described. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.040

文献信息

• Hepatitis C Virus Inhibitors
  申请人：Belema Makonen

  公开号：US20100080772A1

  公开（公告）日：2010-04-01

  The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及使用这些化合物治疗HCV感染的方法。
• HEPATITIS C VIRUS INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP2328865B1

  公开（公告）日：2017-05-31
• US8383094B2
  申请人：——

  公开号：US8383094B2

  公开（公告）日：2013-02-26
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2010039793A1

  公开（公告）日：2010-04-08

  The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
• HCV NS5A replication complex inhibitors. Part 5: Discovery of potent and pan-genotypic glycinamide cap derivatives
  作者：Makonen Belema、Van N. Nguyen、Denis R. St. Laurent、Omar D. Lopez、Yuping Qiu、Andrew C. Good、Peter T. Nower、Lourdes Valera、Donald R. O’Boyle、Jin-Hua Sun、Mengping Liu、Robert A. Fridell、Julie A. Lemm、Min Gao、Jay O. Knipe、Nicholas A. Meanwell、Lawrence B. Snyder

  DOI：10.1016/j.bmcl.2013.05.040

  日期：2013.8

  The isoquinolinamide series of HCV NS5A inhibitors exemplified by compounds 2b and 2c provided the first dual genotype-1a/1b (GT-1a/1b) inhibitor class that demonstrated a significant improvement in potency toward GT-1a replicons compared to that of the initial program lead, stilbene 2a. Structure-activity relationship (SAR) studies that uncovered an alternate phenylglycine-based cap series that exhibit further improvements in virology profile, along with some insights into the pharmacophoric elements associated with the GT-1a potency, are described. (C) 2013 Elsevier Ltd. All rights reserved.