4-(2,6-dimethoxypyrimidin-4-yl)-N-[[4-(trifluoromethoxy)phenyl]methyl]-1-[4-(trifluoromethyl)phenyl]sulfonyl-piperazine-2-carboxamide | 1311150-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(2,6-dimethoxypyrimidin-4-yl)-N-[[4-(trifluoromethoxy)phenyl]methyl]-1-[4-(trifluoromethyl)phenyl]sulfonyl-piperazine-2-carboxamide
• 英文别名: 4-(2,6-dimethoxypyrimidin-4-yl)-N-[[4-(trifluoromethoxy)phenyl]methyl]-1-[4-(trifluoromethyl)phenyl]sulfonylpiperazine-2-carboxamide
• CAS: 1311150-06-7
• 化学式: C₂₆H₂₅F₆N₅O₆S
• 分子量: 649.571
• InChiKey: RBTNDQZGHUHIFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  benzyl 3-((4-(trifluoromethoxy)benzyl)carbamoyl)piperazine-1-carboxylate 在 吡啶 、 甲醇 、 palladium 10% on activated carbon 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 生成 4-(2,6-dimethoxypyrimidin-4-yl)-N-[[4-(trifluoromethoxy)phenyl]methyl]-1-[4-(trifluoromethyl)phenyl]sulfonyl-piperazine-2-carboxamide
  参考文献：
  名称：

  SAR studies on a series of N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamides: Potent inhibitors of the polymerase enzyme (NS5B) of the hepatitis C virus

  摘要：

  Described herein is the initial optimization of (+/-) N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamide (1), a hit discovered in a high throughput screen run against the NS5B polymerase enzyme of the hepatitis C virus. This effort resulted in the identification of (S)-N-sec-butyl-6-((R)-3-(4-(trifluoromethoxy) benzylcarbamoyl)-4-(4-(trifluoromethoxy) phenylsulfonyl)piperazin-1-yl)pyridazine-3-carboxamide (2), that displayed potent replicon activities against HCV genotypes 1b and 1a (EC50 1b/1a = 7/89 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.008

文献信息

• SAR studies on a series of N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamides: Potent inhibitors of the polymerase enzyme (NS5B) of the hepatitis C virus
  作者：Robert G. Gentles、Min Ding、Xiaofan Zheng、Louis Chupak、Michael A. Poss、Brett R. Beno、Lenore Pelosi、Mengping Liu、Julie Lemm、Ying-Kai Wang、Susan Roberts、Min Gao、John Kadow

  DOI：10.1016/j.bmcl.2011.03.008

  日期：2011.5

  Described herein is the initial optimization of (+/-) N-benzyl-4-heteroaryl-1-(phenylsulfonyl)piperazine-2-carboxamide (1), a hit discovered in a high throughput screen run against the NS5B polymerase enzyme of the hepatitis C virus. This effort resulted in the identification of (S)-N-sec-butyl-6-((R)-3-(4-(trifluoromethoxy) benzylcarbamoyl)-4-(4-(trifluoromethoxy) phenylsulfonyl)piperazin-1-yl)pyridazine-3-carboxamide (2), that displayed potent replicon activities against HCV genotypes 1b and 1a (EC50 1b/1a = 7/89 nM). (C) 2011 Elsevier Ltd. All rights reserved.