6-azido-N-naphthalen-1-ylhexanamide | 595607-08-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-azido-N-naphthalen-1-ylhexanamide
• CAS: 595607-08-2
• 化学式: C₁₆H₁₈N₄O
• 分子量: 282.345
• InChiKey: LVYJNOYODXNPEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.86
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-azido-N-naphthalen-1-ylhexanamide 、 3-ethynyl-6-hydroxy-2-(4-methylphenyl)benzofuran-5-carboxylic acid 在 copper(ll) sulfate pentahydrate 、 L-ascorbic acid sodium salt 作用下， 以 水 、 叔丁醇 为溶剂， 生成 6-hydroxy-3-(1-(6-(naphthalen-1-ylamino)-6-oxohexyl)-1H-1,2,3-triazol-4-yl)-2-para-tolylbenzofuran-5-carboxylic acid
  参考文献：
  名称：

  Inhibition of Lymphoid Tyrosine Phosphatase by Benzofuran Salicylic Acids

  摘要：

  The lymphoid tyrosine phosphatase (Lyp, PTPN22) is a critical negative regulator of T cell antigen receptor (TCR) signaling. A single-nucleotide polymorphism (SNP) in the ptpn22 gene correlates with the incidence of various autoimmune diseases, including type I diabetes, rheumatoid arthritis, and systemic lupus erythematosus. Since the disease-associated allele is a more potent inhibitor of TCR signaling, specific Lyp inhibitors May become valuable in treating autoimmunity. Using a structure-based approach, we synthesized a library of 34 compounds that inhibited Lyp with IC50 values between 0.27 and 6.2 mu M. A reporter assay was employed to screen for compounds that enhanced TCR signaling in cells, and several inhibitors displayed a dose-dependent, activating effect. Subsequent probing for Lyp's direct physiological targets by immunoblot analysis confirmed the ability of the compounds to inhibit Lyp in T cells. Selectivity profiling against closely related tyrosine phosphatases and in silico docking studies with the crystal structure of Lyp yielded valuable information for the design of Lyp-specific compounds.

  DOI：

  10.1021/jm101004d
• 作为产物：
  描述：

  6-叠氮基己酸甲酯 在 甲醇 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 6-azido-N-naphthalen-1-ylhexanamide
  参考文献：
  名称：

  Inhibition of Lymphoid Tyrosine Phosphatase by Benzofuran Salicylic Acids

  摘要：

  The lymphoid tyrosine phosphatase (Lyp, PTPN22) is a critical negative regulator of T cell antigen receptor (TCR) signaling. A single-nucleotide polymorphism (SNP) in the ptpn22 gene correlates with the incidence of various autoimmune diseases, including type I diabetes, rheumatoid arthritis, and systemic lupus erythematosus. Since the disease-associated allele is a more potent inhibitor of TCR signaling, specific Lyp inhibitors May become valuable in treating autoimmunity. Using a structure-based approach, we synthesized a library of 34 compounds that inhibited Lyp with IC50 values between 0.27 and 6.2 mu M. A reporter assay was employed to screen for compounds that enhanced TCR signaling in cells, and several inhibitors displayed a dose-dependent, activating effect. Subsequent probing for Lyp's direct physiological targets by immunoblot analysis confirmed the ability of the compounds to inhibit Lyp in T cells. Selectivity profiling against closely related tyrosine phosphatases and in silico docking studies with the crystal structure of Lyp yielded valuable information for the design of Lyp-specific compounds.

  DOI：

  10.1021/jm101004d