ethyl 2-(2-mercaptobenzamido)acetate | 863194-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(2-mercaptobenzamido)acetate
• 英文别名: 2-(2-mercaptobenzamido)acetate；Ethyl 2-[(2-sulfanylbenzoyl)amino]acetate；ethyl 2-[(2-sulfanylbenzoyl)amino]acetate
• CAS: 863194-17-6
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: AZJJZDCZEIQVJP-UHFFFAOYSA-N

物化性质

• 沸点：
  408.6±30.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-mercaptobenzamido)acetate 以 N,N-二甲基乙酰胺 为溶剂， 生成 N-[2-(5-pyridiniovalerylthio)benzoyl]glycine ethyl ester bromide
  参考文献：
  名称：

  Synthesis and Biological Properties of Amino Acid Amide Ligand-Based Pyridinioalkanoyl Thioesters as Anti-HIV Agents

  摘要：

  Hyper-mutable retroviruses such as HIV can become rapidly resistant to drugs used to treat infection, Strategies for coping with drug-resistant strains of virus include combination therapies. using viral protease and reverse transcriptase inhibitors. Another approach is the development of antiviral agents that attack mutationally nonpermissive targets that have functions essential for viral replication. Thus, the highly conserved nucleocapsid protein. NCp7, was chosen as a prime target in our search for novel anti-HIV agents that can overcome the problem of viral drug resistance. Recently, we reported (J. Med. Chem. 1999 42, 67) a novel chemotype, the pyridinioalkanoyl thioesters (PATEs), based on 2-mercaptobenzamides as the thiol component and having its amide nitrogen substituted with various phenylsulfonyl moieties. These compounds were identified as relatively nontoxic anti-HIV agents in the XTT cytoprotection assay. In this study. we wish to report a separate genre of active PATEs wherein the thiol component consists of an N-2-mercaptobenzoyl-amino acid derivative. Active derivatives (EC50 < 10 muM) reported herein were confined to amino acid primary amides or methyl amides having side chains no larger than isobutyl. Amino acids terminating in free carboxyl or carboxylic acid ester groups were mostly inactive. Selected compounds were shown to be active on chronically infected CEM/SK-1, TNFalpha-induced U1. ACH-2 cells and virucidal on cell-free virus, latently infected U I cells and acutely infected primary peripheral blood mononuclear cells (PBMCs). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00392-3
• 作为产物：
  描述：

  硫代水杨酸 在 N-甲基吗啉 、 sodium phosphate buffer 、 二甲基二环氧乙烷 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 丙酮 、 乙腈 为溶剂， 反应 75.25h， 生成 ethyl 2-(2-mercaptobenzamido)acetate
  参考文献：
  名称：

  蛋白质酪氨酸磷酸酶 1B (PTP1B) 活性的氧化还原调节化学模型

  摘要：

  越来越多的证据表明，内源性产生的过氧化氢充当细胞信号分子（除其他外）可以调节某些蛋白磷酸酶的活性。最近的 X 射线晶体学研究揭示了蛋白质酪氨酸磷酸酶 1B 氧化还原调节背后的意外化学转化，其中酶的氧化失活在催化半胱氨酸残基与其相邻的酰胺氮之间产生链内蛋白质交联。这项工作描述了一种有机小分子，它是 PTP1B 活性位点官能团氧化还原传感组装的有效模型。使用该模型系统获得的结果表明 PTP1B 氧化转化为其“交联” 非活性形式可以通过将活性位点半胱氨酸氧化成次磺酸 (RSOH) 直接进行。这种蛋白质交联形成反应的非常容易的性质，以及通过半胱氨酸残基氧化产生的蛋白质次磺酸在细胞中广泛存在，表明在 PTP1B 背景下首次出现的氧化蛋白质交联形成的类型代表蛋白质功能氧化还原“转换”的潜在通用机制。因此，这里表征的化学可能与氧化还原调节的信号转导和氧化应激的毒性作用具有广泛的相关性。随着通过半胱氨酸残

  DOI：

  10.1021/ja052599e

文献信息

• Protection of a single-cysteine redox switch from oxidative destruction: On the functional role of sulfenyl amide formation in the redox-regulated enzyme PTP1B
  作者：Santhosh Sivaramakrishnan、Andrea H. Cummings、Kent S. Gates

  DOI：10.1016/j.bmcl.2009.12.001

  日期：2010.1

  Model reactions offer a chemical mechanism by which formation of a sulfenyl amide residue at the active site of the redox-regulated protein tyrosine phosphatase PTP1B protects the cysteine redox switch in this enzyme against irreversible oxidative destruction. The results suggest that 'overoxidation' of the sulfenyl amide redox switch to the sulfinyl amide in proteins is a chemically reversible event, because the sulfinyl amide can be easily returned to the native cysteine thiol residue via reactions with cellular thiols. (C) 2009 Elsevier Ltd. All rights reserved.
• A Chemical Model for Redox Regulation of Protein Tyrosine Phosphatase 1B (PTP1B) Activity
  作者：Santhosh Sivaramakrishnan、Kripa Keerthi、Kent S. Gates

  DOI：10.1021/ja052599e

  日期：2005.8.1

  of PTP1B. Findings obtained using this model system suggest that the oxidative transformation of PTP1B to its "crosslinked" inactive form can proceed directly via oxidation of the active-site cysteine to a sulfenic acid (RSOH). The remarkably facile nature of this protein cross-link-forming reaction, along with the widespread cellular occurrence of protein sulfenic acids generated via oxidation of cysteine

  越来越多的证据表明，内源性产生的过氧化氢充当细胞信号分子（除其他外）可以调节某些蛋白磷酸酶的活性。最近的 X 射线晶体学研究揭示了蛋白质酪氨酸磷酸酶 1B 氧化还原调节背后的意外化学转化，其中酶的氧化失活在催化半胱氨酸残基与其相邻的酰胺氮之间产生链内蛋白质交联。这项工作描述了一种有机小分子，它是 PTP1B 活性位点官能团氧化还原传感组装的有效模型。使用该模型系统获得的结果表明 PTP1B 氧化转化为其“交联” 非活性形式可以通过将活性位点半胱氨酸氧化成次磺酸 (RSOH) 直接进行。这种蛋白质交联形成反应的非常容易的性质，以及通过半胱氨酸残基氧化产生的蛋白质次磺酸在细胞中广泛存在，表明在 PTP1B 背景下首次出现的氧化蛋白质交联形成的类型代表蛋白质功能氧化还原“转换”的潜在通用机制。因此，这里表征的化学可能与氧化还原调节的信号转导和氧化应激的毒性作用具有广泛的相关性。随着通过半胱氨酸残
• Synthesis and Biological Properties of Amino Acid Amide Ligand-Based Pyridinioalkanoyl Thioesters as Anti-HIV Agents
  作者：Yongsheng Song、Atul Goel、Venkatesha Basrur、Paula E.A Roberts、Judy A Mikovits、John K Inman、Jim A Turpin、William G Rice、Ettore Appella

  DOI：10.1016/s0968-0896(01)00392-3

  日期：2002.5

  Hyper-mutable retroviruses such as HIV can become rapidly resistant to drugs used to treat infection, Strategies for coping with drug-resistant strains of virus include combination therapies. using viral protease and reverse transcriptase inhibitors. Another approach is the development of antiviral agents that attack mutationally nonpermissive targets that have functions essential for viral replication. Thus, the highly conserved nucleocapsid protein. NCp7, was chosen as a prime target in our search for novel anti-HIV agents that can overcome the problem of viral drug resistance. Recently, we reported (J. Med. Chem. 1999 42, 67) a novel chemotype, the pyridinioalkanoyl thioesters (PATEs), based on 2-mercaptobenzamides as the thiol component and having its amide nitrogen substituted with various phenylsulfonyl moieties. These compounds were identified as relatively nontoxic anti-HIV agents in the XTT cytoprotection assay. In this study. we wish to report a separate genre of active PATEs wherein the thiol component consists of an N-2-mercaptobenzoyl-amino acid derivative. Active derivatives (EC50 < 10 muM) reported herein were confined to amino acid primary amides or methyl amides having side chains no larger than isobutyl. Amino acids terminating in free carboxyl or carboxylic acid ester groups were mostly inactive. Selected compounds were shown to be active on chronically infected CEM/SK-1, TNFalpha-induced U1. ACH-2 cells and virucidal on cell-free virus, latently infected U I cells and acutely infected primary peripheral blood mononuclear cells (PBMCs). (C) 2002 Elsevier Science Ltd. All rights reserved.