2-[3-(2-chlorophenyl)pyrazin-2-yl]sulfanyl-1-(3,4-dihydro-1H-isoquinolin-2-yl)ethanone | 1352228-95-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-[3-(2-chlorophenyl)pyrazin-2-yl]sulfanyl-1-(3,4-dihydro-1H-isoquinolin-2-yl)ethanone
• CAS: 1352228-95-5
• 化学式: C₂₁H₁₈ClN₃OS
• 分子量: 395.912
• InChiKey: NCVUVFXHZUCEEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-2-氯苯基甘氨酸甲酯盐酸盐 在 吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 tetraphosphorus decasulfide 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 34.0h， 生成 2-[3-(2-chlorophenyl)pyrazin-2-yl]sulfanyl-1-(3,4-dihydro-1H-isoquinolin-2-yl)ethanone
  参考文献：
  名称：

  Discovery of novel 2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamides as potent HIV-1 inhibitors using a structure-based bioisosterism approach

  摘要：

  The present work is an extension of our ongoing efforts towards the development and identification of new molecules with anti-HIV activity which have previously led to the discovery of arylazolylthioacetanilides as highly active NNRTIs. In this article, a series of 2-2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamide derivatives were synthesized and evaluated for in vitro anti-HIV activity. Most of the tested compounds exhibited moderate activities against wild-type HIV-1. Among them, compound 6k showed significant activity against wild-type HIV-1 with an EC50 value of 1.7 mu M, along with moderate activity against wild-type reverse transcriptase (RT). The preliminary structure-activity relationship (SAR) and docking calculations of this new series of compounds were also investigated, which may help designing more potent molecules. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.058

文献信息

• Discovery of novel 2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamides as potent HIV-1 inhibitors using a structure-based bioisosterism approach
  作者：Peng Zhan、Wenmin Chen、Zhenyu Li、Xiao Li、Xuwang Chen、Ye Tian、Christophe Pannecouque、Erik De Clercq、Xinyong Liu

  DOI：10.1016/j.bmc.2012.09.058

  日期：2012.12

  The present work is an extension of our ongoing efforts towards the development and identification of new molecules with anti-HIV activity which have previously led to the discovery of arylazolylthioacetanilides as highly active NNRTIs. In this article, a series of 2-2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamide derivatives were synthesized and evaluated for in vitro anti-HIV activity. Most of the tested compounds exhibited moderate activities against wild-type HIV-1. Among them, compound 6k showed significant activity against wild-type HIV-1 with an EC50 value of 1.7 mu M, along with moderate activity against wild-type reverse transcriptase (RT). The preliminary structure-activity relationship (SAR) and docking calculations of this new series of compounds were also investigated, which may help designing more potent molecules. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.