(S)-N-(2-hydroxybenzyl)-3-mercapto-2-methylpropanamide | 1521158-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-N-(2-hydroxybenzyl)-3-mercapto-2-methylpropanamide
• 英文别名: (2S)-N-[(2-hydroxyphenyl)methyl]-2-methyl-3-sulfanylpropanamide
• CAS: 1521158-52-0
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: DNPHAXCDWMBBGU-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.33
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (氨基甲基)-苯酚 在 N-甲基吗啉 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-N-(2-hydroxybenzyl)-3-mercapto-2-methylpropanamide
  参考文献：
  名称：

  Simplified captopril analogues as NDM-1 inhibitors

  摘要：

  Captopril is a New Delhi metallo-beta-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 mu M. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, we synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors in order to identify the pharmacophore for NDM-1 inhibition. We found that the lead compound 22 had an IC50 value of 1.0 mu M. Further structure simplification provided compounds 31 and 32, which had IC50 values of 15 and 10 mu M, respectively. As compound 32 is a clinically used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.068

文献信息

• Simplified captopril analogues as NDM-1 inhibitors
  作者：Ningning Li、Yintong Xu、Qiang Xia、Cuigai Bai、Taiyi Wang、Lei Wang、Dingdi He、Nannan Xie、Lixin Li、Jing Wang、Hong-Gang Zhou、Feng Xu、Cheng Yang、Quan Zhang、Zheng Yin、Yu Guo、Yue Chen

  DOI：10.1016/j.bmcl.2013.10.068

  日期：2014.1

  Captopril is a New Delhi metallo-beta-lactamase-1 (NDM-1) inhibitor with an IC50 value of 7.9 mu M. It is composed of two units: a 3-mercapto-2-methylpropanoyl fragment and a proline residue. In this study, we synthesized simple amide derivatives of 3-mercapto-2-methylpropanoic acid, and then tested them as NDM-1 inhibitors in order to identify the pharmacophore for NDM-1 inhibition. We found that the lead compound 22 had an IC50 value of 1.0 mu M. Further structure simplification provided compounds 31 and 32, which had IC50 values of 15 and 10 mu M, respectively. As compound 32 is a clinically used antidote for metal poisoning, it has great potential to be repurposed to treat bacterial infections. (c) 2013 Elsevier Ltd. All rights reserved.