4-methylphenyl 3-aminobenzenesulfonate | 309933-09-3

• 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: 4-methylphenyl 3-aminobenzenesulfonate
• 英文别名: (4-methylphenyl) 3-aminobenzenesulfonate
• CAS: 309933-09-3
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: KEUYFJSQQKNWDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[7-(chlorosulfonyl)(2-naphthyl)]{[7-(chlorosulfonyl)(2-naphthyl)]amino}carboxamide 、 4-methylphenyl 3-aminobenzenesulfonate 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以84%的产率得到4-methylphenyl 3-[({7-[({7-[({3-[(4-methylphenyl)oxysulfonyl]phenyl}amino)sulfonyl]-2-naphthyl}amino)carbonylamino]-2-naphthyl}sulfonyl)amino]benzenesulfonate
  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：

  3-Nitro-benzolsulfonsaeure-<4-methyl-phenylester> 在 盐酸 、 tin(ll) chloride 作用下， 生成 4-methylphenyl 3-aminobenzenesulfonate
  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

文献信息

• Naphthalene ureas as glucose uptake enhancers
  申请人：Telik, Inc.

  公开号：US06458998B1

  公开（公告）日：2002-10-01

  Compounds of formula I are useful for treating conditions associated with hyperglycemia, especially Type II diabetes. These compounds are useful in stimulating the kinase activity of the insulin receptor, activating the insulin receptor, and stimulating the uptake of glucose. Pharmaceutical compositions comprising the antidiabetic compounds are also disclosed.

  化合物I的公式对治疗与高血糖相关的疾病，特别是2型糖尿病，具有益处。这些化合物在刺激胰岛素受体的激酶活性、激活胰岛素受体和促进葡萄糖摄取方面具有用处。还公开了包含抗糖尿病化合物的药物组合物。
• Novel naphthalene ureas as glucose uptake enhancers
  申请人：——

  公开号：US20030135063A1

  公开（公告）日：2003-07-17

  Compounds of formula I are useful for treating conditions associated with hyperglycemia, especially Type II diabetes. These compounds are useful in stimulating the kinase activity of the insulin receptor, activating the insulin receptor, and stimulating the uptake of glucose. Pharmaceutical compositions comprising the antidiabetic compounds are also disclosed.

  公式I的化合物对于治疗与高血糖有关的疾病，特别是2型糖尿病非常有用。这些化合物在刺激胰岛素受体的激酶活性、激活胰岛素受体和促进葡萄糖的摄取方面非常有用。还公开了包含抗糖尿病化合物的药物组合物。
• NAPHTHALENE UREAS AS GLUCOSE UPTAKE ENHANCERS
  申请人：Telik, Inc.

  公开号：EP1181271A2

  公开（公告）日：2002-02-27
• US6458998B1
  申请人：——

  公开号：US6458998B1

  公开（公告）日：2002-10-01
• US7071231B2
  申请人：——

  公开号：US7071231B2

  公开（公告）日：2006-07-04