N-acetyl-N'-(3-nitro-phenyl)-urea | 50610-66-7

• 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-acetyl-N'-(3-nitro-phenyl)-urea
• 英文别名: N-Acetyl-N'-(3-nitro-phenyl)-harnstoff；N-[(3-nitrophenyl)carbamoyl]acetamide
• CAS: 50610-66-7
• 化学式: C₉H₉N₃O₄
• 分子量: 223.188
• InChiKey: CNVCCZGGBORBPS-UHFFFAOYSA-N

物化性质

• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-N'-(3-nitro-phenyl)-urea 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 3-Acetyl-1-(3-aminophenyl)urea
  参考文献：
  名称：

  Synthesis and activity evaluation of phenylurea derivatives as potent antitumor agents

  摘要：

  We have discovered several tubulin-active compounds in our previous studies. In the establishment of a compound library of small molecule weight tubulin ligands, 14 new N-3-haloacylaminophenyl-N'-(alkyl/aryl) urea analogs were designed and synthesized. The structure-activity relationship (SAR) analysis revealed that (i) the order of anticancer potency for the 3-haloacylamino chain was following CH2Br > -CHBrCH3; (ii) the N'-substituent moiety was not essential for the anticancer activity, and a proper alkyl substitution might enhance the anticancer activity. Among these analogs, the compounds 16j bearing bromoacetyl at the N'-end exhibited a potent activity against eight human tumor cell lines, including CEM (leukemia), Daudi (lymphoma), MCF-7 (breast cancer), Bel-7402 (hepatoma), DU-145 (prostate cancer), DND-1A (melanoma), LOVO (colon cancer) and MIA Paca (pancreatic cancer), with the IC50 values between 0.38 and 4.07 mu M. Interestingly, compound 16j killed cancer cells with a mechanism independent of the tubulin-based mechanism, indicating a significant change of the action mode after the structure modi. cation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.022
• 作为产物：
  描述：

  乙酰异氰酸酯 、 间硝基苯胺 以 乙腈 为溶剂， 反应 12.0h， 生成 N-acetyl-N'-(3-nitro-phenyl)-urea
  参考文献：
  名称：

  Synthesis and activity evaluation of phenylurea derivatives as potent antitumor agents

  摘要：

  We have discovered several tubulin-active compounds in our previous studies. In the establishment of a compound library of small molecule weight tubulin ligands, 14 new N-3-haloacylaminophenyl-N'-(alkyl/aryl) urea analogs were designed and synthesized. The structure-activity relationship (SAR) analysis revealed that (i) the order of anticancer potency for the 3-haloacylamino chain was following CH2Br > -CHBrCH3; (ii) the N'-substituent moiety was not essential for the anticancer activity, and a proper alkyl substitution might enhance the anticancer activity. Among these analogs, the compounds 16j bearing bromoacetyl at the N'-end exhibited a potent activity against eight human tumor cell lines, including CEM (leukemia), Daudi (lymphoma), MCF-7 (breast cancer), Bel-7402 (hepatoma), DU-145 (prostate cancer), DND-1A (melanoma), LOVO (colon cancer) and MIA Paca (pancreatic cancer), with the IC50 values between 0.38 and 4.07 mu M. Interestingly, compound 16j killed cancer cells with a mechanism independent of the tubulin-based mechanism, indicating a significant change of the action mode after the structure modi. cation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.022

文献信息

• Sah, Journal of the Chinese Chemical Society (Peking), 1946, vol. 13, p. 22,26,27
  作者：Sah

  DOI：——

  日期：——
• Synthesis and activity evaluation of phenylurea derivatives as potent antitumor agents
  作者：Dan-Qing Song、Na-Na Du、Yue-Ming Wang、Wei-Ying He、En-Zhu Jiang、Shi-Xiang Cheng、Yan-Xiang Wang、Ying-Hong Li、Yu-Ping Wang、Xin Li、Jian-Dong Jiang

  DOI：10.1016/j.bmc.2009.04.022

  日期：2009.6

  We have discovered several tubulin-active compounds in our previous studies. In the establishment of a compound library of small molecule weight tubulin ligands, 14 new N-3-haloacylaminophenyl-N'-(alkyl/aryl) urea analogs were designed and synthesized. The structure-activity relationship (SAR) analysis revealed that (i) the order of anticancer potency for the 3-haloacylamino chain was following CH2Br > -CHBrCH3; (ii) the N'-substituent moiety was not essential for the anticancer activity, and a proper alkyl substitution might enhance the anticancer activity. Among these analogs, the compounds 16j bearing bromoacetyl at the N'-end exhibited a potent activity against eight human tumor cell lines, including CEM (leukemia), Daudi (lymphoma), MCF-7 (breast cancer), Bel-7402 (hepatoma), DU-145 (prostate cancer), DND-1A (melanoma), LOVO (colon cancer) and MIA Paca (pancreatic cancer), with the IC50 values between 0.38 and 4.07 mu M. Interestingly, compound 16j killed cancer cells with a mechanism independent of the tubulin-based mechanism, indicating a significant change of the action mode after the structure modi. cation. (C) 2009 Elsevier Ltd. All rights reserved.