N-[7-(chlorosulfonyl)(2-naphthyl)]-N-(2-{N-[7-(chlorosulfonyl)(2-naphthyl)]acetylamino}ethyl)acetamide | 1069138-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[7-(chlorosulfonyl)(2-naphthyl)]-N-(2-{N-[7-(chlorosulfonyl)(2-naphthyl)]acetylamino}ethyl)acetamide
• 英文别名: 7-[Acetyl-[2-[acetyl-(7-chlorosulfonylnaphthalen-2-yl)amino]ethyl]amino]naphthalene-2-sulfonyl chloride
• CAS: 1069138-80-2
• 化学式: C₂₆H₂₂Cl₂N₂O₆S₂
• 分子量: 593.508
• InChiKey: JJJSOMXEZFUHOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[7-(chlorosulfonyl)(2-naphthyl)]-N-(2-{N-[7-(chlorosulfonyl)(2-naphthyl)]acetylamino}ethyl)acetamide 、 5-氨基-2-氯苯甲酸 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以24%的产率得到5-({[7-(N-{2-[N-(7-{[(3-carboxy-4-chlorophenyl)amino]sulfonyl}(2-naphthyl))acetylamino]ethyl}acetylamino)(2-naphthyl)]sulfonyl}amino)-2-chlorobenzoic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel Insulin Receptor Tyrosine Kinase Activators

  摘要：

  A novel series of symmetrical ureas of [(7-amino(2-naphthyl))sulfonyl]phenylamines were designed, synthesized, and tested for their ability to increase glucose transport in mouse 3T3-L1 adipocytes, a surrogate readout for activation of the insulin receptor (IR) tyrosine kinase (IRTK). A structure-activity relationship was established that indicated glucose transport activity was dependent on the presence of two acidic functionalities, two sulfonamide linkages, and a central urea or 2-imidazolidinone core. Compound 30 was identified as a potent and selective IRTK activator. At low concentrations, 30 was able to increase the tyrosine phosphorylation of the IR stimulated by submaximal insulin. At higher concentrations, 30 was able to increase tyrosine the phosphorylation levels of the IR in the absence of insulin. When administered intraperitoneally (ip) and orally (po), 30 improved glucose tolerance in hypoinsulinemic, streptozotocin-treated rats. These data provide pharmacological validation that small molecule IRTK activators represent a potential new class of antidiabetic agents.

  DOI：

  10.1021/jm800600v
• 作为产物：
  描述：

  7-(N-{2-[N-(7-sulfo-2-naphthyl)acetylamino]ethyl}acetylamino)naphthalene-2-sulfonic acid disodium salt 在 三氯氧磷 作用下， 反应 96.0h， 以90%的产率得到N-[7-(chlorosulfonyl)(2-naphthyl)]-N-(2-{N-[7-(chlorosulfonyl)(2-naphthyl)]acetylamino}ethyl)acetamide
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel Insulin Receptor Tyrosine Kinase Activators

  摘要：

  A novel series of symmetrical ureas of [(7-amino(2-naphthyl))sulfonyl]phenylamines were designed, synthesized, and tested for their ability to increase glucose transport in mouse 3T3-L1 adipocytes, a surrogate readout for activation of the insulin receptor (IR) tyrosine kinase (IRTK). A structure-activity relationship was established that indicated glucose transport activity was dependent on the presence of two acidic functionalities, two sulfonamide linkages, and a central urea or 2-imidazolidinone core. Compound 30 was identified as a potent and selective IRTK activator. At low concentrations, 30 was able to increase the tyrosine phosphorylation of the IR stimulated by submaximal insulin. At higher concentrations, 30 was able to increase tyrosine the phosphorylation levels of the IR in the absence of insulin. When administered intraperitoneally (ip) and orally (po), 30 improved glucose tolerance in hypoinsulinemic, streptozotocin-treated rats. These data provide pharmacological validation that small molecule IRTK activators represent a potential new class of antidiabetic agents.

  DOI：

  10.1021/jm800600v