1-(4-nitrophenyl)-3-(4-(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-nitrophenyl)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea
• 英文别名: 1-(4-Nitrophenyl)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea (e6)；1-(4-nitrophenyl)-3-[4-(2-oxochromen-3-yl)-1,3-thiazol-2-yl]urea
• 化学式: C₁₉H₁₂N₄O₅S
• 分子量: 408.394
• InChiKey: MVTOLEWYNKYMPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 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-乙酰基香豆素 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-nitrophenyl)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea
  参考文献：
  名称：

  枯芳基噻唑衍生物对红细胞碳酸酐酶Ⅰ、Ⅱ的体外抑制作用及构效关系

  摘要：

  掺入尿素的香豆素和杂环化合物由于它们的碳酸酐酶抑制特性而具有作为抗癫痫药、利尿剂和抗青光眼剂的临床应用。我们研究了一系列含有脲/硫脲基团的香豆基噻唑衍生物对碳酸酐酶 I 和 II 的抑制作用。所有研究的化合物对 hCA I 和 hCA II 均表现出抑制活性，其中 1-(3-氯苯基)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea最强的抑制剂。构效关系研究表明，大多数尿素衍生物对 hCA I 和 hCA II 的抑制作用比硫脲衍生物更强。与给电子基团相比，苯环上的吸电子基团增加了抑制活性。

  DOI：

  10.1134/s1068162016050046

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.
• In vitro inhibition effects on erythrocyte carbonic anhydrase I and II and structure-activity relationships of cumarylthiazole derivatives
  作者：Belma Z. Kurt、Fatih Sonmez、Basak Gokce、Adem Ergun、Nahit Gencer、Taki Demir、Oktay Arslan、Mustafa Kucukislamoglu

  DOI：10.1134/s1068162016050046

  日期：2016.9

  Coumarin and heterocyclic compounds incorporating urea have clinical applications as antiepileptics, diuretics, and antiglaucoma agents due to their carbonic anhydrase inhibitory properties. We investigated inhibition of carbonic anhydrase I and II with a series of coumarylthiazole derivatives containing urea/thiourea groups. All the investigated compounds exhibited inhibitory activity on both hCA

  掺入尿素的香豆素和杂环化合物由于它们的碳酸酐酶抑制特性而具有作为抗癫痫药、利尿剂和抗青光眼剂的临床应用。我们研究了一系列含有脲/硫脲基团的香豆基噻唑衍生物对碳酸酐酶 I 和 II 的抑制作用。所有研究的化合物对 hCA I 和 hCA II 均表现出抑制活性，其中 1-(3-氯苯基)-3-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)urea最强的抑制剂。构效关系研究表明，大多数尿素衍生物对 hCA I 和 hCA II 的抑制作用比硫脲衍生物更强。与给电子基团相比，苯环上的吸电子基团增加了抑制活性。