3-(4-氯苯基)-1-甲基咪唑烷-2,4-二酮 | 33093-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 3-(4-氯苯基)-1-甲基咪唑烷-2,4-二酮
• 英文名称: 3-(4-chlorophenyl)-1-methylimidazolidine-2,4-dione
• CAS: 33093-33-3
• 化学式: C₁₀H₉ClN₂O₂
• 分子量: 224.647
• InChiKey: NMYPODRMYJIZIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-氯苯基)-1-甲基咪唑烷-2,4-二酮 以 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到(4E)-3-(4-chlorophenyl)-5-((dimethylamino)methylene)-1-methylimidazolidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 mu M, 0.18 mu M, 0.09 mu M, 0.03 mu M, and 1.06 mu M against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.07.011
• 作为产物：
  描述：

  phenyl N-(4-chlorophenyl)carbamate 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3-(4-氯苯基)-1-甲基咪唑烷-2,4-二酮
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 mu M, 0.18 mu M, 0.09 mu M, 0.03 mu M, and 1.06 mu M against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.07.011

文献信息

• N-(2-fluoro-4-halo-5-substituted phenyl)hydantoins, and their production and use
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0069855A2

  公开（公告）日：1983-01-19

  N-(2-fluoro-4-halo-5-substituted phenyl)hydantoins of the formula: wherein X is a chlorine atom or a bromine atom and R' and R2 are, same or different, each a C1-C4 alkyl group, a cyclopropyl group, a C3-C4 alkenyl group of a C3-C4 alkynyl group are disclosed, which are useful as herbicides.

  式中的 N-(2-氟-4-卤代-5-取代苯基)海因： 其中 X 是氯原子或溴原子，R'和 R2 是相同或不同的 C1-C4 烷基、环丙基、C3-C4 烯基或 C3-C4 烷炔基。
• Cegan, Alexandr; Vecera, Miroslav, Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 6, p. 1521 - 1528
  作者：Cegan, Alexandr、Vecera, Miroslav

  DOI：——

  日期：——
• US4345936A
  申请人：——

  公开号：US4345936A

  公开（公告）日：1982-08-24
• US4427438A
  申请人：——

  公开号：US4427438A

  公开（公告）日：1984-01-24
• US4579688A
  申请人：——

  公开号：US4579688A

  公开（公告）日：1986-04-01