N-(N-acetyl-S-trityl-L-cysteinyl)-S-isobutyrylcysteamine | 681144-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(N-acetyl-S-trityl-L-cysteinyl)-S-isobutyrylcysteamine
• 英文别名: N-(N-acetyl-S-trityl-L-cysteinyl)-S-isobutyryl-cysteamine；S-[2-[[(2R)-2-acetamido-3-tritylsulfanylpropanoyl]amino]ethyl] 2-methylpropanethioate
• CAS: 681144-89-8
• 化学式: C₃₀H₃₄N₂O₃S₂
• 分子量: 534.744
• InChiKey: WBYBYENRVBMFEQ-MHZLTWQESA-N

物化性质

• 沸点：
  736.5±60.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-acetyl-S-trityl-L-cysteinyl)-S-isobutyrylcysteamine 在 吡啶 、 silver nitrate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 14.03h， 生成 N-(N,S-biacetyl-L-cysteinyl)-S-isobutyryl-cysteamine
  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 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 12.75h， 生成 N-(N-acetyl-S-trityl-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

• Novel antioxidants, preparation processes and their uses
  申请人：——

  公开号：US20040158092A1

  公开（公告）日：2004-08-12

  The invention concerns a process for preparing compounds of general formula (I) 1 wherein R and R′ represent an alkyl radical or an aryl group; and R″ is hydrogen or a CO—R 1 group wherein R 1 is an alkyl radical or an aryl group; and wherein these compounds are or not in the thiazolidine form; by protecting the N-acyl-L-cysteine to form an intermediate compound; and then by coupling said intermediate compound with S-acylcysteamine hydrochloride or with thiazolidine.

  这项发明涉及一种制备一般式（I）的化合物的过程 其中R和R′代表烷基基团或芳基；而R″是氢或CO—R 1 基团，其中R 1 是烷基基团或芳基；这些化合物是或不是以噻唑烷形式存在；通过保护N-酰基-L-半胱氨酸形成中间化合物；然后通过将该中间化合物与S-酰基半胱氨酸盐酸盐或噻唑烷偶联。
• 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.
• US6989372B1
  申请人：——

  公开号：US6989372B1

  公开（公告）日：2006-01-24