Ac-Cys(Trt)-ONSu | 73609-53-7

• 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: Ac-Cys(Trt)-ONSu
• 英文别名: Ac-Cys(Trt)-NHS
• CAS: 73609-53-7
• 化学式: C₂₈H₂₆N₂O₅S
• 分子量: 502.591
• InChiKey: ZRDNTYMIWSIWLE-DEOSSOPVSA-N

物化性质

• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Ac-Cys(Trt)-ONSu 在 N-甲基吗啉 、 吡啶 、 silver nitrate 作用下， 以 甲醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 26.03h， 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 作用下， 以 乙酸乙酯 为溶剂， 反应 0.58h， 生成 Ac-Cys(Trt)-ONSu
  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

• 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。
• [EN] INHIBITOR-FUNCTIONALIZED ULTRASMALL NANOPARTICLES AND METHODS THEREOF<br/>[FR] NANOPARTICULES ULTRA-PETITES FONCTIONNALISÉES PAR UN INHIBITEUR ET MÉTHODES ASSOCIÉES
  申请人：MEMORIAL SLOAN KETTERING CANCER CENTER

  公开号：WO2018102372A1

  公开（公告）日：2018-06-07

  Described herein are novel conjugates containing an inhibitor (e.g., a PSMA inhibitor, e.g., a gastrin-releasing peptide receptor inhibitor) and metal chelator that are covalently attached to a macromolecule (e.g., a nanoparticle, a polymer, a protein). Such conjugates exhibit distinct properties over the free, unbound inhibitor/chelator construct.

  本文描述了一种新颖的结合物，其中包含一个抑制剂（例如，PSMA抑制剂，例如，胃泌素释放肽受体抑制剂）和金属螯合剂，它们以共价键连接到大分子（例如，纳米颗粒，聚合物，蛋白质）上。这种结合物在自由的未结合抑制剂/螯合剂构造体上表现出独特的特性。
• N-Acetyl-[2-(O-methyl)tyrosine]arginine-vasopressin, an interesting antagonist of the vasopressor response to vasopressin
  作者：David A. Jones、Wilbur H. Sawyer

  DOI：10.1021/jm00180a027

  日期：1980.6

  tyrosine]arginine-vasopressin [Ac-Tyr(Me)AVP] was undertaken utilizing a combination of the stepwise active ester and fragment condensation methods. Ac-Tyr(Me)AVP is an antagonist of the vasopressor response to vasopressin (pA2 = 7.18 +/- 0.08), devoid of vasopressor agonist activity, and has an antidiuretic potency of 0.026 +/- 0.002 unit/mg, a 15 000-fold decrease over the antidiuretic activity of

  N-乙酰基-[2-（O-甲基）酪氨酸]精氨酸-加压素[Ac-Tyr（Me）AVP]的合成是采用逐步活性酯和片段缩合方法的结合进行的。Ac-Tyr（Me）AVP是抗升压药的抗升压药的拮抗剂（pA2 = 7.18 +/- 0.08），没有升压药的激动剂活性，抗利尿药的效力为0.026 +/- 0.002单位/ mg，15000比[2-（O-甲基）酪氨酸]精氨酸加压素的抗利尿作用降低了两倍。该类似物还是催产素体外子宫内缩酮活性的拮抗剂，在不存在Mg2 +的情况下，pA2值为7.29 +/- 0.08，在0.5 mM Mg2 +中的pA2值为6.73 +/- 0.14。
• Substrate-Initiated Synthesis of Cell-Penetrating Poly(disulfide)s
  作者：Eun-Kyoung Bang、Giulio Gasparini、Guillaume Molinard、Aurélien Roux、Naomi Sakai、Stefan Matile

  DOI：10.1021/ja311961k

  日期：2013.2.13

  applied to grow cell-penetrating poly(disulfide)s directly on substrates of free choice. Reductive depolymerization after cellular uptake should then release the native substrates and minimize toxicity. In the presence of thiolated substrates, propagators containing a strained disulfide from asparagusic or, preferably, lipoic acid and a guanidinium cation polymerize into poly(disulfide)s in less than

  表面引发聚合的经验应用于直接在自由选择的基材上生长细胞穿透性聚（二硫化物）。细胞摄取后的还原性解聚应该释放天然底物并将毒性降至最低。在硫醇化底物存在的情况下，含有来自芦笋或优选硫辛酸的应变二硫化物和胍鎓阳离子的增殖剂在室温和 pH 7 下在不到 5 分钟内聚合成聚（二硫化物）。阳离子聚的底物引发的聚合(二硫化物)及其与二硫苏糖醇的解聚导致荧光囊泡中运输活性的出现和消失。凝胶渗透色谱法和荧光共振能量转移进一步表征了相同的过程。
• 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.