N-(2-methylphenyl)-N'-(6-nitrobenzothiazol-2-yl)urea | 352526-25-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-methylphenyl)-N'-(6-nitrobenzothiazol-2-yl)urea
• 英文别名: 1-(2-Methylphenyl)-3-(6-nitro-1,3-benzothiazol-2-yl)urea
• CAS: 352526-25-1
• 化学式: C₁₅H₁₂N₄O₃S
• 分子量: 328.351
• InChiKey: BKIIKZJRBUCRTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  丙二酸 、 N-(2-methylphenyl)-N'-(6-nitrobenzothiazol-2-yl)urea 在 乙酰氯 作用下， 反应 4.0h， 以82%的产率得到1-(2-methylphenyl)-3-(6-nitro-1,3-benzothiazol-2-yl)hexahydro-2,4,6-pyrimidinetrione
  参考文献：
  名称：

  掺入苯并噻唑的巴比妥酸衍生物：合成和抗惊厥药筛选

  摘要：

  以取代苯胺为原料合成了一系列1-(6-取代-1,3-苯并噻唑-2-基)-3-(取代苯基)六氢-2,4,6-嘧啶三酮4a-t。这些化合物含有两种活性抗惊厥药效团，苯并噻唑和巴比妥酸。基于不同的光谱技术确认了化合物的结构。评价所有化合物的抗惊厥活性。三种化合物 4c、4d 和 4s 在最大电击癫痫试验 (MES) 和皮下戊四唑试验 (scPTZ) 中显示出有希望的抗惊厥活性。在进行最小运动损伤测试时，它们还显示出广泛的安全性。

  DOI：

  10.1002/ardp.200900002
• 作为产物：
  描述：

  2-氨基-6-硝基苯并噻唑 、 2,2,2-三氯-N-(2-甲基苯基)乙酰胺 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.07h， 以78%的产率得到N-(2-methylphenyl)-N'-(6-nitrobenzothiazol-2-yl)urea
  参考文献：
  名称：

  Microwave Promoted Environmentally Benign Synthesis of 2-Aminobenzothiazoles and Their Urea Derivatives

  摘要：

  2-Aminobenzothiazoles were efficiently synthesized using stable, crystalline tetrabutylammonium tribromide instead of toxic, corrosive liquid bromine under solvent-free and microwave irradiation condition. Furthermore, benzothiazol-2-ylureas were synthesized in good to high yield by reactions of 2-aminobenzothiazoles with N-trichloroacetanilides, which were used as a substitute for toxic, unstable isocyanates, under microwave irradiation condition. This protocol has advantages of no utilization of hazardous chemicals, rapid reaction rate, high yield, and easy work-up procedure.

  DOI：

  10.1080/10426500701578506

文献信息

• [EN] UREA DERIVATIVES FOR TREATING AND/OR PREVENTING CANCER<br/>[FR] DÉRIVÉS D'URÉE POUR LE TRAITEMENT ET/OU LA PRÉVENTION DU CANCER
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2020079184A2

  公开（公告）日：2020-04-23

  The present invention relates to a compound or a pharmaceutically acceptable salt thereof of formulae (I) and (II), and a pharmaceutical composition comprising such compound for use for treating a cancer, particularly a cancer overexpressing CXCR1 and CXCR2 receptors, such as medulloblastoma, head and neck and kidney cancer. The invention further relates to such compounds for use for treating macular degeneration.
• Benzothiazole Incorporated Barbituric Acid Derivatives: Synthesis and Anticonvulsant Screening
  作者：Nadeem Siddiqui、Waquar Ahsan

  DOI：10.1002/ardp.200900002

  日期：2009.8

  3‐benzothiazol‐2‐yl)‐3‐(substituted phenyl)hexahydro‐2,4,6‐pyrimidinetriones 4a–t were synthesized starting from substituted anilines. These compounds contained two active anticonvulsant pharmacophores, benzothiazole and barbituric acid. Structures of the compounds were confirmed on the basis of different spectroscopic techniques. All the compounds were evaluated for their anticonvulsant activity. Three

  以取代苯胺为原料合成了一系列1-(6-取代-1,3-苯并噻唑-2-基)-3-(取代苯基)六氢-2,4,6-嘧啶三酮4a-t。这些化合物含有两种活性抗惊厥药效团，苯并噻唑和巴比妥酸。基于不同的光谱技术确认了化合物的结构。评价所有化合物的抗惊厥活性。三种化合物 4c、4d 和 4s 在最大电击癫痫试验 (MES) 和皮下戊四唑试验 (scPTZ) 中显示出有希望的抗惊厥活性。在进行最小运动损伤测试时，它们还显示出广泛的安全性。
• Microwave Promoted Environmentally Benign Synthesis of 2-Aminobenzothiazoles and Their Urea Derivatives
  作者：Zheng Li、Shuxiu Xiao、Guoqiang Tian、Anguo Zhu、Xu Feng、Jing Liu

  DOI：10.1080/10426500701578506

  日期：2008.4.18

  2-Aminobenzothiazoles were efficiently synthesized using stable, crystalline tetrabutylammonium tribromide instead of toxic, corrosive liquid bromine under solvent-free and microwave irradiation condition. Furthermore, benzothiazol-2-ylureas were synthesized in good to high yield by reactions of 2-aminobenzothiazoles with N-trichloroacetanilides, which were used as a substitute for toxic, unstable isocyanates, under microwave irradiation condition. This protocol has advantages of no utilization of hazardous chemicals, rapid reaction rate, high yield, and easy work-up procedure.