N-(1,3-benzothiazol-2-yl)-N'-(4-methylphenyl)urea | 26135-24-0

• 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-(1,3-benzothiazol-2-yl)-N'-(4-methylphenyl)urea
• 英文别名: 1-(benzo[d]thiazol-2-yl)-3-(p-tolyl)urea；1-benzothiazol-2-yl-3-p-tolyl-urea；N-(1,3-benzothiazol-2-yl)-N'-(4-methylphenyl) urea；1-(1,3-benzothiazol-2-yl)-3-(4-methylphenyl)urea
• CAS: 26135-24-0
• 化学式: C₁₅H₁₃N₃OS
• 分子量: 283.354
• InChiKey: XKBLYCUDHQRLDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 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：
  82.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯胺 在 溴 作用下， 以 乙腈 为溶剂， 生成 N-(1,3-benzothiazol-2-yl)-N'-(4-methylphenyl)urea
  参考文献：
  名称：

  1-（苯并[ d ]噻唑-2-基）-3-（取代的芳基）脲衍生物作为新型抗帕金森病药物的基于结构的设计，合成和分子建模研究

  摘要：

  1-（苯并[ d 设计并合成了]噻唑-2-基）-3-（取代的芳基）脲衍生物，这是我们努力发现新颖的抗帕金森病药物的作用，该药物在氟哌啶醇诱导的僵直症和小鼠氧化应激中具有改善的药理作用。发现所有化合物都具有减轻氟哌啶醇诱导的小鼠僵直的活性。糠基，2-和/或3-甲氧基取代的苯基衍生物作为有效试剂出现。除2-氯，5-三氟甲基取代的类似物外，卤素取代的衍生物表现出中等的抗帕金森氏活性。对脑匀浆中的丙二醛（MDA），谷胱甘肽（GSH），超氧化物歧化酶（SOD）和谷胱甘肽过氧化物酶（GSH-Px）进行了生化评估，以突出与它们相关的神经保护特性。2A受体表现出非常好的结合相互作用，需要进行进一步的研究以确认它们与人A 2A受体的结合，以设计和开发有效的拮抗剂。Lipinski规则5的参数是通过计算得出的，因为体内的药代动力学和代谢行为通常与化合物的物理性质有关。合成的化合物均未违反Lipinski规则，因此不适合治疗帕金森氏病。

  DOI：

  10.1007/s00044-011-9786-y

文献信息

• Synthesis, enzyme inhibition and anticancer investigation of unsymmetrical 1,3-disubstituted ureas
  作者：Sana Mustafa、Shahnaz Perveen、Ajmal Khan

  DOI：10.2298/jsc121212076m

  日期：——

  In this research work seventeen urea derivatives, including five new derivatives N-mesityl-N'-(3-methylphenyl)urea (2), N-(3-methoxyphenyl)-N'-(3-methylphenyl)urea (4), N-mesityl-N'-(4-methylphenyl)urea (6), N-(1,3-benzothiazol-2-yl)-N'-(3-methylphenyl)urea (9) and N-(2-methylphenyl)-2-oxo-1-pyrrolidinecarboxamide (15) have synthesized by reacting ortho, meta and para tolyl isocyanate with primary and secondary amines by previously reported method. We exhibited all series (1-17) to urease, ?-glucuronidase and snake venom phosphodiesterase enzyme inhibition assays. The ranges of % inhibition for urease, ?-glucuronidase and phosphodiesterase enzymes were 0.3-45.3, 4.9-44.9 and 1.2-46.4 % respectively. Moreover, the effect of these compounds on prostate cancer cell lines was also observed. The new compound N-(1,3-benzothiazol-2-yl)-N'-(3-methylphenyl)urea (9) showed in vitro anticancer activity with IC50 value of 78.28 ? 1.2 ?M. All the compounds were characterized by state of art spectroscopic techniques.

  在这项研究工作中，17 种脲衍生物，包括 5 种新的 衍生物 N-甲磺酰基-N'-(3-甲基苯基)脲 (2) N-(3-甲氧基苯基)-N'-(3-甲基苯基)脲 (4)、 N-甲磺酰基-N'-（4-甲基苯基）脲 (6)、 N-(1,3-苯并噻唑-2-基)-N'-(3-甲基苯基)脲（9）和 和 N-(2-甲基苯基)-2-氧代-1-吡咯烷甲酰胺（15）的合成方法如下 通过正、偏和对位异氰酸甲苯酯与伯胺和仲胺反应合成了 N-（2-甲基苯基）-2-氧代-1-吡咯烷甲酰胺（15）。 胺反应合成的。我们对所有系列（1-17）的 脲酶、葡糖醛酸酶和蛇毒磷酸二酯酶的酶抑制试验。 测定。对脲酶、葡萄糖醛酸酶和磷酸二酯酶的抑制率范围为 磷酸二酯酶的抑制率范围分别为 0.3-45.3%、4.9-44.9% 和 1.2-46.4%。 和 1.2-46.4 %。此外，还观察到了这些化合物对前列腺癌细胞系的影响。 此外，还观察到了这些化合物对前列腺癌细胞系的影响。新化合物 新化合物 N-(1,3-苯并噻唑-2-基)-N'-(3-甲基苯基)脲（9）显示出体外 抗癌活性，IC50 值为 78.28 ?1.2 ?M.所有化合物 所有化合物均采用最先进的光谱技术进行表征。
• TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY
  申请人：Wynne Graham Michael

  公开号：US20090075938A1

  公开（公告）日：2009-03-19

  There are disclosed compound of Formula (1): A 1 , A 2 , A 3 and A 4 which may be the same or different, represent N or CR 1 , X is a divalent group selected from O, S(O) n , C═W, NR 4 , NC(═O)R 5 and CR 6 R 7 , W is O, S, NR 20 , Y is N or CR 8 , one of R 4 , R 5 , R 6 , R 8 , R 9 and NR 20 represents -L-R 3 , in which L is a single bond or a linker group, additionally, R 1 , R 3 -R 9 , which may be the same or different, independently represent hydrogen or a substituent and R 20 represents hydrogen, hydroxyl, alkyl optionally substituted by aryl, alkoxy optionally substituted by aryl, aryl, CN, optionally substituted alkoxy, optionally substituted aryloxy, optionally substitute alkanoyl, optionally substituted aroyl, NO 2 , NR 30 R 31 , in which R 30 and R 31 , which may be the same or different, represent hydrogen, optionally substituted alkyl or optionally substituted aryl; additionally, one of R 30 and R 31 may represent optionally substituted alkanoyl or optionally substituted aroyl, n represents an integer from 0 to 2, in addition, when an adjacent pair of A 1 -A 4 each represent CR 1 , then the adjacent carbon atoms, together with their substituents may form a ring B, when X is CR 6 R 7 , R 6 and R 7 , together with the carbon atom to which they are attached may form a ring C, or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the therapeutic and/or prophylactic treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia.

  公式（1）的化合物被揭示：A1，A2，A3和A4，它们可以相同或不同，代表N或CR1，X是从O，S（O）n，C═W，NR4，NC（═O）R5和CR6R7中选择的二价基团，W是O，S，NR20，Y是N或CR8，R4，R5，R6，R8，R9和NR20中的一个表示-L-R3，在其中L是单键或连接基团，此外，R1，R3-R9可以相同或不同，独立地表示氢或取代基，R20表示氢，羟基，可以用芳基取代的烷基，可以用芳基取代的烷氧基，芳基，CN，可以用芳基取代的烷氧基，可以用芳基取代的芳氧基，可以用取代基取代的烷酰基，可以用取代基取代的芳酰基，NO2，NR30R31，在其中R30和R31可以相同或不同，表示氢，可选地取代的烷基或可选地取代的芳基；此外，R30和R31中的一个可以表示可选地取代的烷酰基或可选地取代的芳酰基，n表示从0到2的整数，另外，当相邻的A1-A4中的一对表示CR1时，那么相邻的碳原子及其取代基可以形成环B，当X为CR6R7时，R6和R7与它们附着的碳原子一起可以形成环C，或其药学上可接受的盐，在制造用于治疗和/或预防杜氏肌萎缩症，贝克肌萎缩症或消瘦症的药物时使用。
• Drug Combinations for the Treatment of Duchenne Muscular Dystrophy
  申请人：Wynne Graham Michael

  公开号：US20110195932A1

  公开（公告）日：2011-08-11

  Combinations comprising (or consisting essentially of) one or more compounds of formula (1) with one or more ancillary agents, to processes for preparing the combinations, and to various therapeutic uses of the combinations. Also provided are pharmaceutical compositions containing the combinations as well as a method of treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia using the combinations.

  本发明涉及与一种或多种化合物（1）的一个或多个辅助剂组合的组合物，以制备这些组合物的过程，以及这些组合物的各种治疗用途。还提供了包含这些组合物的制药组合物，以及使用这些组合物治疗杜氏肌营养不良症、贝克肌营养不良症或消瘦的方法。
• DRUG COMBINATIONS FOR THE TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY
  申请人：Summit Corporation PLC

  公开号：US20140011782A1

  公开（公告）日：2014-01-09

  Combinations comprising (or consisting essentially of) one or more compounds of formula (1) with one or more ancillary agents, to processes for preparing the combinations, and to various therapeutic uses of the combinations. Also provided are pharmaceutical compositions containing the combinations as well as a method of treatment of Duchenne muscular dystrophy, Becker muscular dystrophy or cachexia using the combinations.

  该专利涉及包含（或基本上由）一个或多个式（1）化合物和一个或多个辅助剂的组合物，以及制备这些组合物的方法，以及这些组合物的各种治疗用途。此外，还提供了包含这些组合物的药物组合物以及使用这些组合物治疗杜兴肌肉萎缩症，贝克肌肉萎缩症或消瘦症的方法。
• Unsymmetrical 1,3-disubstituted urea derivatives as α-chymotrypsin inhibitors
  作者：Shahnaz Perveen、Sana Mustafa、Mehreen Latif、Lubna Iqbal、Tanzil H. Usmani、Khalid Mohammed Khan、Wolfgang Voelter

  DOI：10.1007/s00044-014-0930-3

  日期：2014.7

  The objective of this study was to synthesize potent and/or novel inhibitors for alpha-chymotrypsin activity. Eighteen derivatives of N-methylphenyl-N'-(alkyl/aryl) urea (1-18) were synthesized, and their inhibitory effects on alpha-chymotrypsin enzyme were evaluated. Two compounds exhibited potent inhibitory activities. The most potent, N-(2-methylphenyl)-2-oxo-1-pyrrolidinecarboxamide (15) having a methyl group at ortho position was the most active inhibitor with an IC50 value of 8.10 +/- A 0.14 mu M, which was comparable to standard chymostatin (IC50 = 8.24 +/- A 0.11 mu M). A slightly less potent, N-(2-acetylphenyl)-N'-(3-methylphenyl) urea (10), exhibited an IC50 of 13.6 +/- A 0.23 mu M. Compounds 3, 4, 7, 11, and 13 exhibited moderate activities. The results demonstrated that alpha-chymotrypsin inhibition is related to the position of the methyl group and the presence of substituent at the nitrogen of the urea bridge. The inhibitory trend suggests that alpha-chymotrypsin inhibitory activity declines with ortho > meta > para substitution order. In conclusion, our data suggest that the compound 15 may serve as a lead compound for further designing of other potent or novel alpha-chymotrypsin inhibitors.