N-[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]{[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]amino}carboxamide | 309933-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]{[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]amino}carboxamide
• 英文别名: 7-{[(7-(chlorosulfonyl)-5-hydroxy(2-naphthyl))amino]carbonylamino}-4-hydroxynaphthalene-2-sulfonyl chloride；7-[(7-Chlorosulfonyl-5-hydroxynaphthalen-2-yl)carbamoylamino]-4-hydroxynaphthalene-2-sulfonyl chloride
• CAS: 309933-11-7
• 化学式: C₂₁H₁₄Cl₂N₂O₇S₂
• 分子量: 541.389
• InChiKey: LECPJAJDVLYVQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  167
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]{[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]amino}carboxamide 、 5-氨基水杨酸 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以5%的产率得到5-{[(7-{[(7-{[(3-carboxy-4-hydroxyphenyl)amino]sulfonyl}-5-hydroxy(2-naphthyl))amino]carbonylamino}-4-hydroxy(2-naphthyl))sulfonyl]amino}-2-hydroxybenzoic 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：

  AMI-1 以 环丁砜 、 异丁酰胺 、 乙腈 、 三氯氧磷 为溶剂， 生成 N-[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]{[7-(chlorosulfonyl)-5-hydroxy(2-naphthyl)]amino}carboxamide
  参考文献：
  名称：

  Naphthalene ureas as glucose uptake enhancers

  摘要：

  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。

  公开号：

  US06458998B1

文献信息

• Insulin receptor activators for the treatment of metabolic disorders induced by treatment with HIV protease inhibitors
  申请人：——

  公开号：US20020061927A1

  公开（公告）日：2002-05-23

  Methods of treating a person suffering from HIV protease inhibitor-induced metabolic disorders such as lipodystrophy, hypertriglyceridemia, insulin resistance, hyperglycemia, diabetes and ketoacidosis, comprise treatment with an insulin receptor activating compound, optionally in conjunction with insulin. In general, any insulin receptor activating compound is suitable for the practice of the invention; and preferred compounds are disclosed.

  治疗HIV蛋白酶抑制剂引起的代谢紊乱，如脂肪萎缩症、高甘油三酯血症、胰岛素抵抗、高血糖、糖尿病和酮症的方法，包括使用一种胰岛素受体激活化合物进行治疗，可选地与胰岛素一起使用。一般来说，任何胰岛素受体激活化合物都适用于本发明的实施；并且优选化合物已被披露。
• 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。
• Method for determining whether a compound is an insulin receptor kinase activator
  申请人：——

  公开号：US20020151542A1

  公开（公告）日：2002-10-17

  A method for determining whether a compound is an insulin receptor kinase activator.

  一种确定化合物是否为胰岛素受体激酶激活剂的方法。
• NAPHTHALENE UREAS AS GLUCOSE UPTAKE ENHANCERS
  申请人：Telik, Inc.

  公开号：EP1181271A2

  公开（公告）日：2002-02-27
• INSULIN RECEPTOR ACTIVATORS FOR THE TREATMENT OF METABOLIC DISORDERS IN HUMANS RESULTING FROM TREATMENT OF HIV INFECTION WITH HIV PROTEASE INHIBITORS
  申请人：TELIK, INC.

  公开号：EP1355698A2

  公开（公告）日：2003-10-29