N-(3-chlorophenyl)-N'-(3-methoxyphenyl)-urea | 195133-51-8

• 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-chlorophenyl)-N'-(3-methoxyphenyl)-urea
• 英文别名: 1-(3-chlorophenyl)-3-(3-methoxyphenyl)urea
• CAS: 195133-51-8
• 化学式: C₁₄H₁₃ClN₂O₂
• 分子量: 276.722
• InChiKey: LECRHGUJKBBYEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C(Solv: ethanol (64-17-5))
• 沸点：
  326.0±27.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

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：
  0.07
• 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-chlorophenyl)-N'-(3-methoxyphenyl)-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 6.25h， 生成 1-(3-chlorophenyl)-3-(3-((3-methylbut-2-en-1-yl)oxy)phenyl)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-氯苯胺 、 3-甲氧基苯异氰酸 以 二氯甲烷 为溶剂， 以82.6%的产率得到N-(3-chlorophenyl)-N'-(3-methoxyphenyl)-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

• Unsymmetrically disubstituted urea derivatives: A potent class of antiglycating agents
  作者：Khalid M. Khan、Sumayya Saeed、Muhammad Ali、Madiha Gohar、Javariya Zahid、Ambreen Khan、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bmc.2009.01.075

  日期：2009.3

  A series of unsymmetrically disubstituted urea derivatives 1–28 has been synthesized and screened for their antiglycation activity in vitro. Compounds 26 (IC50 = 4.26 ± 0.25 μM), 1 (IC50 = 5.8 ± 0.08 μM), 22 (IC50 = 4.26 ± 0.25 μM), 6 (IC50 = 6.4 ± 0.02 μM), 5 (IC50 = 6.6 ± 0.26 μM), 2 (IC50 = 7.02 ± 0.31 μM), 3 (IC50 = 7.14 ± 0.84 μM), 27 (IC50 = 7.27 ± 0.36 μM), 4 (IC50 = 8.16 ± 1.04 μM), 21 (IC50 = 8

  一系列不对称脲衍生物的1 - 28已被合成并筛选其体外抗糖化活性。化合物26（IC 50  = 4.26±0.25μM），1（IC 50  = 5.8±0.08μM），22（IC 50  = 4.26±0.25μM），6（IC 50  = 6.4±0.02μM），5（IC 50  = 6.6±0.26μM），2（IC 50  = 7.02±0.31μM），3（IC 50  = 7.14±0.84μM），27（IC 50  = 7.27±0.36μM），4（IC 50  = 8.16±1.04μM），21（IC 50  = 8.4±0.15μM），23（IC 50  = 9.0±0.35μM）和1 3（IC 50  = 15.22±6.7μM）表现出优异的抗糖化活性优于标准品（芦丁，IC 50  = 41.9±2.3μM）。因此，这项研究为抗糖化剂的进一步研究提供了一系列潜在的分子。
• Bokade, Raksha S.; Korpe, Gajanan V., Indian Journal of Heterocyclic Chemistry, 2015, vol. 24, # 3, p. 283 - 288
  作者：Bokade, Raksha S.、Korpe, Gajanan V.

  DOI：——

  日期：——
• 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.