N-(N-acetyl-L-cysteinyl)-S-isobutyrylcysteamine | 311343-15-4

• 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-L-cysteinyl)-S-isobutyrylcysteamine
• 英文别名: S-[2-[[(2R)-2-acetamido-3-sulfanyl-propanoyl]amino]ethyl] 2-methylpropanethioate；S-[2-[[(2R)-2-acetamido-3-sulfanylpropanoyl]amino]ethyl] 2-methylpropanethioate
• CAS: 311343-15-4
• 化学式: C₁₁H₂₀N₂O₃S₂
• 分子量: 292.423
• InChiKey: BHPQLUJLEGGJCF-VIFPVBQESA-N

物化性质

• 沸点：
  541.6±50.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基乙酰氯 、 N-(N-acetyl-L-cysteinyl)-S-isobutyrylcysteamine 在 吡啶 作用下， 以64%的产率得到N-(N-acetyl-S-pivaloyl-L-cysteinyl)-S-isobutyrylcysteamine
  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
• 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-L-cysteinyl)-S-isobutyrylcysteamine
  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

• Synthesis of new N-isobutyryl-l-cysteine/MEA conjugates: Evaluation of their free radical-scavenging activities and anti-HIV properties in human macrophages
  作者：Michael Smietana、Pascal Clayette、Patricia Mialocq、Jean-Jacques Vasseur、Joël Oiry

  DOI：10.1016/j.bioorg.2008.02.001

  日期：2008.6

  Four novel N-isobutyryl-L-cysteine/2-mercaptoethylamine (MEA, cysteamine) conjugates have been designed and synthesized. The antioxidant activities of these new series were evaluated by three different free radical scavenging methods (DPPH test, ABTS test, and deoxyribose assay) and their metal binding capacity was evaluated by the ethidium bromide fluorescence binding assay. These results were compared with those obtained with their pro-GSH acetyl analogues recently developed in our laboratory. We observed that most of these compounds exhibit free radical-scavenging activities similar to those of Trolox, but always superior than NAC. While none of these new derivatives had pro-GSH activities, they displayed anti-HIV properties in human monocyte-derived macrophages infected in vitro. The present study demonstrates that these new N-isobutyryl derivatives, which are expected to have a greater bioavailability than their acetyl analogues, may have useful applications in HIV infection in respect to their antioxidant and anti-HIV activities. (C) 2008 Elsevier Inc. All rights reserved.
• 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.