1-[Diethylamino(phenyl)methylidene]-3-methylthiourea | 76407-01-7

• 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: 1-[Diethylamino(phenyl)methylidene]-3-methylthiourea
• 英文别名: 1-[diethylamino(phenyl)methylidene]-3-methylthiourea
• CAS: 76407-01-7
• 化学式: C₁₃H₁₉N₃S
• 分子量: 249.38
• InChiKey: VQNDPCNBTDDPHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[Diethylamino(phenyl)methylidene]-3-methylthiourea 、 alpha-溴-4-甲氧基苯乙酮 以 乙腈 为溶剂， 反应 5.0h， 生成 (4-methoxyphenyl)(2-(methylamino)-4-phenylthiazol-5-yl)methanone
  参考文献：
  名称：

  2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists

  摘要：

  A series of 2-amino-5-benzoyl-4-phenylthiazole derivatives was investigated in radioligand binding studies at adenosine receptor (AdoR) subtypes with the goal to obtain potent and A(1)-selective antagonists. Acylation of the 2-amino group was found to be crucial for high A(1) affinity. The best compound of the present series was 2-benzoylamino-5-p-methylbenzoyl-4-phenylthiazole (16m) showing a K-i value of 4.83 nM at rat and 57.4 nM at human A(1) receptors combined with high selectivity versus the other AdoR subtypes. The compound behaved as an antagonist in GTP shift assays at A(1) receptors. Compound 16m may serve as a new lead structure for the development of second-generation non-xanthine-derived A(1) antagonists which have potential as novel drugs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.072
• 作为产物：
  描述：

  N,N-diethylbenzamidine 、 异硫氰酸甲酯 生成 1-[Diethylamino(phenyl)methylidene]-3-methylthiourea
  参考文献：
  名称：

  Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents

  摘要：

  A series of 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives were designed and synthesized. Synthesized molecules were further evaluated for their inhibitory activity towards transcription factors NF-kappa B and AP-1 mediated transcriptional activation in a cell line based in vitro as well as for their anti-inflammatory activity in in vivo model of acute inflammation. This series provides us with selective and dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation which also exhibit significant efficacy in in vivo model of inflammation. Two of the compounds 9m and 9o turned out to be the most promising dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation with an IC50 of 3.3 mu M for both. 9n (IC50 = 5.5 mu M) and 9p (IC50 = 5.5 mu M) emerged as selective inhibitors of NF-kappa B mediated transcriptional activation and 9c (IC50 = 5.5 mu M) and 9d (IC50 = 5.5 mu M) were found to be more selective inhibitor of AP-1 mediated transcriptional activity. Though the relationship between the activities shown by these compounds in in vivo and in vitro model is still to be established, these results suggest the suitability of the designed molecular framework as a potential anti-inflammatory molecular framework which also exhibits the inhibitory activity towards NF-kappa B and AP-1 mediated transcriptional activation. This will be worth studying further to explore its complete potential particularly in chronic inflammatory conditions. The structure activity relationship (SAR) of this series has been discussed herein. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.031

文献信息

• Design, synthesis and characterization of novel 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives as inhibitors of NF-κB and AP-1 mediated transcription activation and as potential anti-inflammatory agents
  作者：Rajan S. Giri、Hardik M. Thaker、Tony Giordano、Jill Williams、Donna Rogers、Vasudevan Sudersanam、Kamala K. Vasu

  DOI：10.1016/j.ejmech.2008.10.031

  日期：2009.5

  A series of 2-(2,4-disubstituted-thiazole-5-yl)-3-aryl-3H-quinazoline-4-one derivatives were designed and synthesized. Synthesized molecules were further evaluated for their inhibitory activity towards transcription factors NF-kappa B and AP-1 mediated transcriptional activation in a cell line based in vitro as well as for their anti-inflammatory activity in in vivo model of acute inflammation. This series provides us with selective and dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation which also exhibit significant efficacy in in vivo model of inflammation. Two of the compounds 9m and 9o turned out to be the most promising dual inhibitors of NF-kappa B and AP-1 mediated transcriptional activation with an IC50 of 3.3 mu M for both. 9n (IC50 = 5.5 mu M) and 9p (IC50 = 5.5 mu M) emerged as selective inhibitors of NF-kappa B mediated transcriptional activation and 9c (IC50 = 5.5 mu M) and 9d (IC50 = 5.5 mu M) were found to be more selective inhibitor of AP-1 mediated transcriptional activity. Though the relationship between the activities shown by these compounds in in vivo and in vitro model is still to be established, these results suggest the suitability of the designed molecular framework as a potential anti-inflammatory molecular framework which also exhibits the inhibitory activity towards NF-kappa B and AP-1 mediated transcriptional activation. This will be worth studying further to explore its complete potential particularly in chronic inflammatory conditions. The structure activity relationship (SAR) of this series has been discussed herein. (C) 2008 Elsevier Masson SAS. All rights reserved.
• 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists
  作者：Anja B. Scheiff、Swapnil G. Yerande、Ali El-Tayeb、Wenjin Li、Gajanan S. Inamdar、Kamala K. Vasu、Vasudevan Sudarsanam、Christa E. Müller

  DOI：10.1016/j.bmc.2010.01.072

  日期：2010.3

  A series of 2-amino-5-benzoyl-4-phenylthiazole derivatives was investigated in radioligand binding studies at adenosine receptor (AdoR) subtypes with the goal to obtain potent and A(1)-selective antagonists. Acylation of the 2-amino group was found to be crucial for high A(1) affinity. The best compound of the present series was 2-benzoylamino-5-p-methylbenzoyl-4-phenylthiazole (16m) showing a K-i value of 4.83 nM at rat and 57.4 nM at human A(1) receptors combined with high selectivity versus the other AdoR subtypes. The compound behaved as an antagonist in GTP shift assays at A(1) receptors. Compound 16m may serve as a new lead structure for the development of second-generation non-xanthine-derived A(1) antagonists which have potential as novel drugs. (C) 2010 Elsevier Ltd. All rights reserved.