N-(N-acetyl-S-benzoyl-L-cysteinyl)-S-pivaloylcysteamine

• 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: N-(N-acetyl-S-benzoyl-L-cysteinyl)-S-pivaloylcysteamine
• 英文别名: N-(N-acetyl-S-benzoyl-L-cysteinyl)-S-pivaloyl-cysteamine；S-[(2R)-2-acetamido-3-[2-(2,2-dimethylpropanoylsulfanyl)ethylamino]-3-oxopropyl] benzenecarbothioate
• 化学式: C₁₉H₂₆N₂O₄S₂
• 分子量: 410.558
• InChiKey: BKLTXVJRTMNCQL-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-乙酰基-S-三苯甲基-L-半胱氨酸 在 N-甲基吗啉 、 吡啶 、 silver nitrate 、 氯甲酸异丁酯 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 26.78h， 生成 N-(N-acetyl-S-benzoyl-L-cysteinyl)-S-pivaloylcysteamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation in Human Monocyte-Derived Macrophages of N-(N-Acetyl-l-cysteinyl)-S-acetylcysteamine Analogues with Potent Antioxidant and Anti-HIV Activities

  摘要：

  We synthesized a series of N-(N-acetyl-L-eysteinyl)-S-acetylcysteamine (10) analogues bearing various acyl groups on thiol cysteine or cysteamine residues, to investigate the structure-activity relationship for pro-GSH and anti-HIV properties in human macrophages. The S-substituents were ranked in the following order of efficacy: H greater than or equal to acetyl > isobutyryl > pivaloyl > benzoyl. We found that none of these derivatives had pro-GSH or antiviral activities in vitro higher than that of 10, but several displayed similar levels of anti-HIV activity, making them possible candidates for use as adjuvant therapies in conjunction with HAART, for treating neurological aspects of HIV infection.

  DOI：

  10.1021/jm030374d

文献信息

• US6979747B2
  申请人：——

  公开号：US6979747B2

  公开（公告）日：2005-12-27
• US6989372B1
  申请人：——

  公开号：US6989372B1

  公开（公告）日：2006-01-24
• Synthesis and Biological Evaluation in Human Monocyte-Derived Macrophages of <i>N</i>-(<i>N</i>-Acetyl-<scp>l</scp>-cysteinyl)-<i>S</i>-acetylcysteamine Analogues with Potent Antioxidant and Anti-HIV Activities
  作者：Joël Oiry、Patricia Mialocq、Jean-Yves Puy、Philippe Fretier、Nathalie Dereuddre-Bosquet、Dominique Dormont、Jean-Louis Imbach、Pascal Clayette

  DOI：10.1021/jm030374d

  日期：2004.3.1

  We synthesized a series of N-(N-acetyl-L-eysteinyl)-S-acetylcysteamine (10) analogues bearing various acyl groups on thiol cysteine or cysteamine residues, to investigate the structure-activity relationship for pro-GSH and anti-HIV properties in human macrophages. The S-substituents were ranked in the following order of efficacy: H greater than or equal to acetyl > isobutyryl > pivaloyl > benzoyl. We found that none of these derivatives had pro-GSH or antiviral activities in vitro higher than that of 10, but several displayed similar levels of anti-HIV activity, making them possible candidates for use as adjuvant therapies in conjunction with HAART, for treating neurological aspects of HIV infection.