3-[[4-(4-氯苯基)-1,3-噻唑-2-基]氨基甲酰]丙酸 | 71576-05-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-[[4-(4-氯苯基)-1,3-噻唑-2-基]氨基甲酰]丙酸
• 中文别名: 6-氨基-2-苯基-4H-苯并[h]色烯-4-酮
• 英文名称: 4-(4-(4-chlorophenyl)thiazol-2-ylamino)-4-oxobutanoic acid
• 英文别名: Butanoic acid, 4-((4-(4-chlorophenyl)-2-thiazolyl)amino)-4-oxo-；4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]-4-oxobutanoic acid
• CAS: 71576-05-1
• 化学式: C₁₃H₁₁ClN₂O₃S
• 分子量: 310.761
• InChiKey: WPLOAXKRIROSCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[[4-(4-氯苯基)-1,3-噻唑-2-基]氨基甲酰]丙酸 、 9-(4-aminobutylamino)-1,2,3,4-tetrahydroacridine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以18%的产率得到N¹-(4-(4-chlorophenyl)thiazol-2-yl)-N⁴-(4-(1,2,3,4-tetrahydroacridin-9-ylamino)butyl)succinamide
  参考文献：
  名称：

  Novel multipotent phenylthiazole–tacrine hybrids for the inhibition of cholinesterase activity, β-amyloid aggregation and Ca2+ overload

  摘要：

  In this study, a series of multipotent phenylthiazole-tacrine hybrids (7a-7e, 8, and 9a-9m) were synthesized and biologically evaluated. Screening results showed that phenylthiazole-tacrine hybrids were potent cholinesterase inhibitors with pIC(50) (-logIC(50)) value ranging from 5.78 +/- 0.05 to 7.14 +/- 0.01 for acetylcholinesterase (AChE), and from 5.75 +/- 0.03 to 10.35 +/- 0.15 for butyrylcholinesterase (BuChE). The second series of phenylthiazole-tacrine hybrids (9a-9m) could efficiently prevent A beta(1-42) self-aggregation. The structure-activity relationship revealed that their inhibitory potency relied on the type of middle linker and substitutions at 4'-position of 4-phenyl-2-aminothiazole. In addition, 7a and 7c also displayed the Ca2+ overload blockade effect in the primary cultured cortical neurons. Consequently, these compounds emerged as promising molecules for the therapy of Alzheimer's disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.040
• 作为产物：
  描述：

  2-氨基-4-(4-氯苯基)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 3-[[4-(4-氯苯基)-1,3-噻唑-2-基]氨基甲酰]丙酸
  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

• Evaluation of 3-carbamoylpropanoic acid analogs as inhibitors of human hypoxia-inducible factor (HIF) prolyl hydroxylase domain enzymes
  作者：MuiPhin Chong、LeeRoy Toh、Anthony Tumber、YanYing Chan、MunChiang Chan、Martine I. Abboud、Christopher J. Schofield、KarKheng Yeoh

  DOI：10.1007/s00044-020-02681-7

  日期：2021.4
• 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.
• Novel multipotent phenylthiazole–tacrine hybrids for the inhibition of cholinesterase activity, β-amyloid aggregation and Ca2+ overload
  作者：Yue Wang、Fang Wang、Jun-Ping Yu、Feng-Chao Jiang、Xin-Lei Guan、Can-Ming Wang、Lei Li、Hui Cao、Ming-Xing Li、Jian-Guo Chen

  DOI：10.1016/j.bmc.2012.08.040

  日期：2012.11

  In this study, a series of multipotent phenylthiazole-tacrine hybrids (7a-7e, 8, and 9a-9m) were synthesized and biologically evaluated. Screening results showed that phenylthiazole-tacrine hybrids were potent cholinesterase inhibitors with pIC(50) (-logIC(50)) value ranging from 5.78 +/- 0.05 to 7.14 +/- 0.01 for acetylcholinesterase (AChE), and from 5.75 +/- 0.03 to 10.35 +/- 0.15 for butyrylcholinesterase (BuChE). The second series of phenylthiazole-tacrine hybrids (9a-9m) could efficiently prevent A beta(1-42) self-aggregation. The structure-activity relationship revealed that their inhibitory potency relied on the type of middle linker and substitutions at 4'-position of 4-phenyl-2-aminothiazole. In addition, 7a and 7c also displayed the Ca2+ overload blockade effect in the primary cultured cortical neurons. Consequently, these compounds emerged as promising molecules for the therapy of Alzheimer's disease. (C) 2012 Elsevier Ltd. All rights reserved.