(S)-methyl 6-amino-2-(4-amino-3-((S)-2-aminohexanamido)benzamido)hexanoate

• 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: (S)-methyl 6-amino-2-(4-amino-3-((S)-2-aminohexanamido)benzamido)hexanoate
• 英文别名: methyl (2S)-6-amino-2-[[4-amino-3-[[(2S)-2-aminohexanoyl]amino]benzoyl]amino]hexanoate
• 化学式: C₂₀H₃₃N₅O₄
• 分子量: 407.513
• InChiKey: JVBSUICWFWXURK-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4-二氨基苯甲酸甲酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (S)-methyl 6-amino-2-(4-amino-3-((S)-2-aminohexanamido)benzamido)hexanoate
  参考文献：
  名称：

  3,4-Diaminobenzoic Acid Derivatives as Inhibitors of the Oxytocinase Subfamily of M1 Aminopeptidases with Immune-Regulating Properties

  摘要：

  Members of the oxytocinase subfamily of M1 aminopeptidases (ERAP1, ERAP2, and IRAP) play important roles in both the adaptive and innate human immune responses. Their enzymatic activity can contribute to the pathogenesis of several major human diseases ranging from viral and parasitic infections to autoimmunity and cancer. We have previously demonstrated that diaminobenzoic acid derivatives show promise as selective inhibitors for this group of aminopeptidases. In this study, we have thoroughly explored a series of 3,4-diaminobenzoic acid derivatives as inhibitors of this class of enzymes, achieving submicromolar inhibitors for ERAP2 (IC50 = 237 nM) and IRAP (IC50 = 105 nM). Cell-based analysis indicated that the lead compounds can be effective in downregulating macrophage activation induced by lipopolysaccharide and interferon-gamma as well as cross-presentation by bone marrow-derived dendritic cells. Our results indicate that this class of inhibitors may be useful for the targeted downregulation of immune responses.

  DOI：

  10.1021/jm501867s