(E)-3-(1-(4-isopropylbenzyl)-1H-indol-3-yl)acrylic acid | 1376446-97-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-3-(1-(4-isopropylbenzyl)-1H-indol-3-yl)acrylic acid
• 英文别名: (E)-3-[1-[(4-propan-2-ylphenyl)methyl]indol-3-yl]prop-2-enoic acid
• CAS: 1376446-97-7
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: JIBCYWABMQLUMR-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙二酸 、 1-(4-isopropylbenzyl)-1H-indole-3-carbaldehyde 在 哌啶 、 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以65.8%的产率得到(E)-3-(1-(4-isopropylbenzyl)-1H-indol-3-yl)acrylic 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

• 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.