Methyl 4-[[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]amino]-4-oxobutanoate | 1007788-41-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Methyl 4-[[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]amino]-4-oxobutanoate
• CAS: 1007788-41-1
• 化学式: C₁₄H₁₂F₂N₂O₃S
• 分子量: 326.324
• InChiKey: DQRAPMYELDBMCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 4-[[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]amino]-4-oxobutanoate 在 sodium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.5h， 以48.5%的产率得到3-{[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]carbamoyl}propanoic 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
• 作为产物：
  描述：

  3',4'-二氟苯乙酮 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 、 copper(ll) bromide 作用下， 以 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 反应 26.5h， 生成 Methyl 4-[[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]amino]-4-oxobutanoate
  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