N-(3-methoxyphenyl)-N'-(3-methylphenyl)urea | 445023-82-5

• 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-(3-methoxyphenyl)-N'-(3-methylphenyl)urea
• 英文别名: 1-(3-methoxyphenyl)-3-(m-tolyl)urea；1-(3-Methoxyphenyl)-3-(3-methylphenyl)urea
• CAS: 445023-82-5
• 化学式: C₁₅H₁₆N₂O₂
• mdl: MFCD03073642
• 分子量: 256.304
• InChiKey: RYADNXJEFFDVJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-methoxyphenyl)-N'-(3-methylphenyl)urea 在 偶氮二甲酸二异丙酯 、 氢溴酸 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.25h， 生成 1-(3-((3-methylbut-2-en-1-yl)oxy)phenyl)-3-(m-tolyl)urea
  参考文献：
  名称：

  Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea

  摘要：

  Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among the 39 synthesized molecules, compounds 46, 57, 58 and 86 showed MIC values <= 10 mu g/ml against H37Rv and mc(2)6030 strains. The best molecule with a methyl at ortho position of the first aromatic ring and prenyl group at the meta position of the second aromatic ring showed the MIC value of 5.2 mu g/ml and mu g/ml against H37Rv and mc(2)6030 respectively, with mammalian cytotoxicity of 163.4 mu g/ml. The effective compounds showed selective inhibitory effect on mycolic acid (epoxy mycolate) biosynthesis in C-14-radiolabelled assay. At the same time these molecules also executed their potent immunomodulatory activity by up-regulation of IFN-gamma and IL-12 and down-regulation of IL-10. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.083
• 作为产物：
  描述：

  3-甲基苯胺 、 3-甲氧基苯异氰酸 以 二氯甲烷 为溶剂， 以64.8%的产率得到N-(3-methoxyphenyl)-N'-(3-methylphenyl)urea
  参考文献：
  名称：

  Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea

  摘要：

  Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among the 39 synthesized molecules, compounds 46, 57, 58 and 86 showed MIC values <= 10 mu g/ml against H37Rv and mc(2)6030 strains. The best molecule with a methyl at ortho position of the first aromatic ring and prenyl group at the meta position of the second aromatic ring showed the MIC value of 5.2 mu g/ml and mu g/ml against H37Rv and mc(2)6030 respectively, with mammalian cytotoxicity of 163.4 mu g/ml. The effective compounds showed selective inhibitory effect on mycolic acid (epoxy mycolate) biosynthesis in C-14-radiolabelled assay. At the same time these molecules also executed their potent immunomodulatory activity by up-regulation of IFN-gamma and IL-12 and down-regulation of IL-10. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.083

文献信息

• [EN] COMPOSITIONS AND METHODS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE TRAITEMENT DU CANCER
  申请人：UNIV DUKE

  公开号：WO2020123675A1

  公开（公告）日：2020-06-18

  This disclosure relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating diseases related to Heat Shock Transcription Factor 1 (HSF1) activity and/or function. More particularly, this disclosure relates to methods of inhibiting HSF1 activity with these compounds and pharmaceutical compositions thereof, and methods of treating diseases associated with HSF1 activity and/or function, such as cancer.

  这份披露涉及化合物、包括它们的药物组合物，以及使用这些化合物和组合物治疗与热休克转录因子1（HSF1）活性和/或功能相关疾病的方法。更具体地，这份披露涉及使用这些化合物和药物组合物抑制HSF1活性的方法，以及治疗与HSF1活性和/或功能相关的疾病的方法，如癌症。
• 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。
• 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.
• Attenuation of Mycobacterium species through direct and macrophage mediated pathway by unsymmetrical diaryl urea
  作者：Anand Babu Velappan、Mamilla R. Charan Raja、Dhrubajyoti Datta、Yi Ting Tsai、Iman Halloum、Baojie Wan、Laurent Kremer、Hugo Gramajo、Scott G. Franzblau、Santanu Kar Mahapatra、Joy Debnath

  DOI：10.1016/j.ejmech.2016.09.083

  日期：2017.1

  Tuberculosis is a major threat for mankind and the emergence of resistance strain of Mycobacterium tuberculosis (Mtb) against first line antibiotics makes it lethal for human civilization. In this study, we have synthesized different diaryl urea derivatives targeting the inhibition of mycolic acid biosynthesis. Among the 39 synthesized molecules, compounds 46, 57, 58 and 86 showed MIC values <= 10 mu g/ml against H37Rv and mc(2)6030 strains. The best molecule with a methyl at ortho position of the first aromatic ring and prenyl group at the meta position of the second aromatic ring showed the MIC value of 5.2 mu g/ml and mu g/ml against H37Rv and mc(2)6030 respectively, with mammalian cytotoxicity of 163.4 mu g/ml. The effective compounds showed selective inhibitory effect on mycolic acid (epoxy mycolate) biosynthesis in C-14-radiolabelled assay. At the same time these molecules also executed their potent immunomodulatory activity by up-regulation of IFN-gamma and IL-12 and down-regulation of IL-10. (C) 2016 Elsevier Masson SAS. All rights reserved.