I 152 | 311343-11-0

• 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: I 152
• 英文别名: N-(N-acetyl-L-cysteinyl)-S-acetylcysteamine；Ethanethioic acid, S-(2-(((2R)-2-(acetylamino)-3-mercapto-1-oxopropyl)amino)ethyl)ester；S-[2-[[(2R)-2-acetamido-3-sulfanylpropanoyl]amino]ethyl] ethanethioate
• CAS: 311343-11-0
• 化学式: C₉H₁₆N₂O₃S₂
• 分子量: 264.37
• InChiKey: PCFWUYJHCYCQKP-QMMMGPOBSA-N

物化性质

• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

I-152是一种含有N-乙酰半胱氨酸（NAC）和半胱胺（MEA）的缀合物，能够激活NRF2和ATF4信号，并且具有抗增殖作用。

反应信息

• 作为反应物：
  描述：

  I 152 在 异丁酰氯 作用下， 以56%的产率得到N-(N-acetyl-S-isobutyryl-L-cysteinyl)-S-acetylcysteamine
  参考文献：
  名称：

  Novel antioxidants, preparation processes and their uses

  摘要：

  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。

  公开号：

  US20040158092A1
• 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 、 甲醇 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 26.58h， 生成 I 152
  参考文献：
  名称：

  NAC/MEA Conjugate: A New Potent Antioxidant which Increases the GSH Level in Various Cell Lines

  摘要：

  I-152 is a prodrug of NAC and MEA with potent pro-GSH effects in human macrophages, astrocytes and lymphocytes. This molecule could be of interest in HIV infection in respect to its antioxidant and anti-HIV activities, but also in other diseases to counteract oxidative stress, that is, inflammation, cardiovascular diseases, and neurodegenerative diseases. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00171-8

文献信息

• Antioxidants, preparation processes and their uses
  申请人：Oiry Joel

  公开号：US06979747B2

  公开（公告）日：2005-12-27

  The invention concerns a process for preparing compounds of general formula (I) 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.

  本发明涉及一种制备一般式（I）化合物的方法，其中R和R'代表烷基基团或芳基基团；而R"是氢或CO-R1基团，其中R1是烷基基团或芳基基团；这些化合物是否处于噻唑烷形式。该方法通过保护N-酰基-L-半胱氨酸形成中间化合物，然后通过与S-酰基半胱氨酸盐酸盐或噻唑烷偶联来制备所述中间化合物。
• Antioxidants, preparation methods and uses
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US06989372B1

  公开（公告）日：2006-01-24

  The invention concerns compounds of general formula (I) (wherein R and R′ represent an alkyl radical or an aryl group and R″ is hydrogen or a CO—R1 group wherein R1 is an alkyl radical or an aryl group; and the dimers formed by the disulphide bond from one and/or the other of the two sulphur atoms of the compounds of general formula (I); and the corresponding thiazolidin forms), the methods for preparing them and uses thereof. More particularly, it concerns the use of said compounds as antioxidant agents, in particular for preparing medicines designed to increase the intracellular and/or extracellular level of glutathione (GSH).

  本发明涉及通式（I）化合物（其中R和R'代表烷基或芳基基团，R"是氢或CO-R1基团，其中R1是烷基或芳基基团；以及由通式（I）化合物的两个硫原子中的一个或另一个形成的二硫键所形成的二聚体；以及相应的噻唑烷形式），其制备方法和用途。更具体地，涉及使用所述化合物作为抗氧化剂，特别是用于制备旨在增加谷胱甘肽（GSH）细胞内和/或细胞外水平的药物。
• Dithiol Based on <scp>l</scp>-Cysteine and Cysteamine as a Disulfide-Reducing Agent
  作者：Francesca Bartoccini、Michele Retini、Rita Crinelli、Michele Menotta、Alessandra Fraternale、Giovanni Piersanti

  DOI：10.1021/acs.joc.2c01050

  日期：2022.8.5

  We report the synthesis, chemical properties, and disulfide bond-reducing performance of a dithiol called NACMEAA, conceived as a hybrid of two biologically relevant thiols: cysteine and cysteamine. NACMEAA is conveniently prepared from inexpensive l-cystine in an efficient manner. As a nonvolatile, highly soluble, and neutral compound at physiological pH with the first thiol pKa value of 8.0, NACMEAA

  我们报告了一种名为 NACMEAA 的二硫醇的合成、化学性质和二硫键还原性能，该二硫醇被认为是两种生物学相关的硫醇的混合物：半胱氨酸和半胱胺。NACMEAA 是由廉价的l-胱氨酸以有效的方式方便地制备的。作为一种非挥发性、高溶解性和中性化合物，在生理 pH 值下，第一硫醇 p K值为8.0，NACMEAA 具有反应性和用户友好性。我们还证明 NACMEAA 可减少 GSSG 和溶菌酶中的二硫键。
• 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.
• 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.