(S)-2-{2-[2-((S)-1,3-Dicarbamoyl-propylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-pentanedioic acid diamide | 713090-23-4

• 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: (S)-2-{2-[2-((S)-1,3-Dicarbamoyl-propylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-pentanedioic acid diamide
• CAS: 713090-23-4
• 化学式: C₂₄H₂₈N₆O₆S₂
• 分子量: 560.655
• InChiKey: FPQGMAOLDWWNCU-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  230.56
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{2-[2-((S)-1,3-Dicarbamoyl-propylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-pentanedioic acid diamide 在 tris(carboxyethyl)phosphine hydrochloride 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-{4-[2-((S)-1,3-Dicarbamoyl-propylcarbamoyl)-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 N-甲基吗啉 、 氯化亚砜 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 (S)-2-{2-[2-((S)-1,3-Dicarbamoyl-propylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-pentanedioic acid diamide
  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