N-(2-mercaptobenzoyl)-L-alaninamide | 449775-53-5

• 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: N-(2-mercaptobenzoyl)-L-alaninamide
• 英文别名: N-[(2S)-1-amino-1-oxopropan-2-yl]-2-sulfanylbenzamide
• CAS: 449775-53-5
• 化学式: C₁₀H₁₂N₂O₂S
• 分子量: 224.283
• InChiKey: ZBASXCRSAAVKFK-LURJTMIESA-N

物化性质

• 沸点：
  485.4±30.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-mercaptobenzoyl)-L-alaninamide 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 生成 1-{4-[2-((S)-1-Carbamoyl-ethylcarbamoyl)-phenylsulfanylcarbonyl]-butyl}-pyridinium; 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：

  2, 2'-二硫代二苯甲酸 在 三(2-羰基乙基)磷盐酸盐 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 N-(2-mercaptobenzoyl)-L-alaninamide
  参考文献：
  名称：

  基于苯甲酰胺的硫代氨基甲酸酯：一类新的HIV-1 NCp7抑制剂。

  摘要：

  HIV-1核衣壳蛋白NCp7包含两个高度保守的锌指，由于其在病毒复制中起关键作用并且具有突变耐受性，因此被用作AIDS治疗的新靶标。在本文中，我们报告了一类新的具有良好抗病毒活性和低细胞毒性的NCp7抑制剂。

  DOI：

  10.1016/s0960-894x(02)00007-0

文献信息

• Benzamide-Based Thiolcarbamates: A New Class of HIV-1 NCp7 Inhibitors
  作者：Atul Goel、Sharlyn J. Mazur、Rasem J. Fattah、Tracy L. Hartman、Jim A. Turpin、Mingjun Huang、William G. Rice、Ettore Appella、John K. Inman

  DOI：10.1016/s0960-894x(02)00007-0

  日期：2002.3

  The HIV-1 nucleocapsid protein NCp7, which contains two highly conserved zinc fingers, is being used as a novel target for AIDS therapy due to its pivotal role in viral replication and its mutationally intolerant nature. Herein we report a new class of NCp7 inhibitors that possess good antiviral activity with low cellular toxicity.

  HIV-1核衣壳蛋白NCp7包含两个高度保守的锌指，由于其在病毒复制中起关键作用并且具有突变耐受性，因此被用作AIDS治疗的新靶标。在本文中，我们报告了一类新的具有良好抗病毒活性和低细胞毒性的NCp7抑制剂。
• Acylthiols and component thiol compositions as anti-hiv and anti-retroviral agents
  申请人：Inman K. John

  公开号：US20050020831A1

  公开（公告）日：2005-01-27

  Certain thiol and acylthiol compounds inhibit retrovirus growth by attacking the highly conserved zinc finger regions of essential viral proteins. These compounds, compositions containing them, and methods of using them to treat retroviral infections such as HIV are described. These compounds are also useful for preparation of vaccines comprised of inactivated retroviruses such as HIV, prevention of the transmission of such retroviruses, and detection of retroviral proteins.

  某些硫醇和酰硫醇化合物通过攻击必要病毒蛋白的高度保守的锌指区域来抑制逆转录病毒的生长。本文介绍了这些化合物、含有它们的组合物以及使用它们治疗逆转录病毒感染（如HIV）的方法。这些化合物还可用于制备由灭活的逆转录病毒（如HIV）组成的疫苗、预防这些逆转录病毒的传播以及检测逆转录病毒蛋白。
• ACYTHIOLS AND COMPONENT THIOL COMPOSITIONS AS ANTI-HIV AND ANTI-RETROVIRAL AGENTS
  申请人：Inman John K.

  公开号：US20090247473A1

  公开（公告）日：2009-10-01

  Certain thiol and acylthiol compounds inhibit retrovirus growth by attacking the highly conserved zinc finger regions of essential viral proteins. These compounds, compositions containing them, and methods of using them to treat retroviral infections such as HIV are described. These compounds are also useful for preparation of vaccines comprised of inactivated retroviruses such as HIV, prevention of the transmission of such retroviruses, and detection of retroviral proteins.

  某些硫醇和酰硫醇化合物通过攻击必要病毒蛋白质高度保守的锌指区域来抑制逆转录病毒的生长。本文描述了这些化合物、含有它们的组合物以及使用它们治疗逆转录病毒感染（如HIV）的方法。这些化合物还可用于制备由灭活逆转录病毒（如HIV）组成的疫苗，预防这种逆转录病毒的传播以及检测逆转录病毒蛋白质。
• ACYLTHIOLS AND COMPONENT THIOL COMPOSITIONS AS ANTI-HIV AND ANTI-RETROVIRAL AGENTS
  申请人：The Gov. of USA, as represented by the Secretary, Dept. of Health and Human services, National Institutes of Health

  公开号：EP1425262A1

  公开（公告）日：2004-06-09
• Acylthiols and compositions thereof as anti-HIV and anti-retroviral agents
  申请人：The Gov. of USA, as represented by the Secretary, Dept. of Health and Human services, National Institutes of Health

  公开号：EP1425262B1

  公开（公告）日：2014-01-08