1-(4-chlorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 1-(4-chlorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea
• 英文别名: 1-(4-Chlorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e32)；1-(4-chlorophenyl)-3-[4-(6-nitro-2-oxochromen-3-yl)-1,3-thiazol-2-yl]urea
• 化学式: C₁₉H₁₁ClN₄O₅S
• 分子量: 442.839
• InChiKey: ARVGXCRGJGDWSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-乙酰基-6-硝基-2H-苯并吡喃-2-酮 在 溴 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 13.25h， 生成 1-(4-chlorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea
  参考文献：
  名称：

  Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives

  摘要：

  A newly series of coumarylthiazole derivatives containing aryl urea/thiourea groups were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized compounds exhibited inhibitory activity to both cholinesterases. Among them, 1-(4-(8-methoxy-2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-(4-chlorophenyl)thiourea (f8, IC50 = 4.58 mu M) was found to be the most active compound against AChE, and 1-(4-fluorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e31) exhibited the strongest inhibition against BuChE with IC50 value of 4.93 mu M, which was 3.5-fold more potent than that of galantamine. The selectivity of f8 and e31 were 2.64 and 0.04, respectively. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were investigated for antioxidant activity. Among them, f8, f4 and f6 (IC50 = 1.64, 1.82 and 2.69 mu M, respectively) showed significantly better ABTS cation radical scavenging ability than standard quercetin (IC50 = 15.49 mu M). (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.02.002

文献信息

• Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives
  作者：Belma Zengin Kurt、Isil Gazioglu、Fatih Sonmez、Mustafa Kucukislamoglu

  DOI：10.1016/j.bioorg.2015.02.002

  日期：2015.4

  A newly series of coumarylthiazole derivatives containing aryl urea/thiourea groups were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized compounds exhibited inhibitory activity to both cholinesterases. Among them, 1-(4-(8-methoxy-2-oxo-2H-chromen-3-yl)thiazol-2-yl)-3-(4-chlorophenyl)thiourea (f8, IC50 = 4.58 mu M) was found to be the most active compound against AChE, and 1-(4-fluorophenyl)-3-(4-(6-nitro-2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e31) exhibited the strongest inhibition against BuChE with IC50 value of 4.93 mu M, which was 3.5-fold more potent than that of galantamine. The selectivity of f8 and e31 were 2.64 and 0.04, respectively. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were investigated for antioxidant activity. Among them, f8, f4 and f6 (IC50 = 1.64, 1.82 and 2.69 mu M, respectively) showed significantly better ABTS cation radical scavenging ability than standard quercetin (IC50 = 15.49 mu M). (C) 2015 Elsevier Inc. All rights reserved.