4-((4-(naphthalen-2-yl)thiazol-2-yl)amino)-4-oxobutanoic acid | 284488-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-((4-(naphthalen-2-yl)thiazol-2-yl)amino)-4-oxobutanoic acid
• 英文别名: 4-[(4-Naphthalen-2-yl-1,3-thiazol-2-yl)amino]-4-oxobutanoic acid
• CAS: 284488-51-3
• 化学式: C₁₇H₁₄N₂O₃S
• 分子量: 326.376
• InChiKey: WWFNNEMQTKPRFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-4-(2-萘基)噻唑 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 26.5h， 生成 4-((4-(naphthalen-2-yl)thiazol-2-yl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes

  摘要：

  Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-alpha. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 mu M and a binding affinity for ap2 with the apparent K-i values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.006

文献信息

• Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same
  申请人：——

  公开号：US20030185793A1

  公开（公告）日：2003-10-02

  The invention relates to transport molecule binding ligand compounds which comprise a therapeutically and/or diagnostically active substance and a carrier molecule-affine substance with a high association constant to the carrier molecule. The invention also relates to medicaments containing these ligand compounds and to diagnostic kits.

  这项发明涉及与载体分子结合的配体化合物，其包括具有治疗和/或诊断活性物质以及与载体分子具有高结合常数的载体分子亲和物质。该发明还涉及含有这些配体化合物的药物和诊断试剂盒。
• THERAPEUTISCHE UND DIAGNOSTISCHE LIGANDENSYSTEME MIT TRANSPORTMOLEKÜLBINDENDEN EIGENSCHAFTEN UND DIESE ENTHALTENDE ARZNEIMITTEL
  申请人：KTB Tumorforschungsgesellschaft mbH

  公开号：EP1272223B1

  公开（公告）日：2006-05-31
• US7902144B2
  申请人：——

  公开号：US7902144B2

  公开（公告）日：2011-03-08
• Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes
  作者：Qinyuan Xu、Li Huang、Juan Liu、Liang Ma、Tao Chen、Jinying Chen、Fei Peng、Dong Cao、Zhuang Yang、Neng Qiu、Jingxiang Qiu、Guangcheng Wang、Xiaolin Liang、Aihua Peng、Mingli Xiang、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.ejmech.2012.03.006

  日期：2012.6

  Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-alpha. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 mu M and a binding affinity for ap2 with the apparent K-i values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent. (C) 2012 Elsevier Masson SAS. All rights reserved.