1-phenylazo-2-(4-thiomorpholino)ethene | 1079286-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 1-phenylazo-2-(4-thiomorpholino)ethene
• 英文别名: Phenyl(2-thiomorpholinovinyl)diazene；phenyl(2-thiomorpholin-4-ylethenyl)diazene
• CAS: 1079286-54-6
• 化学式: C₁₂H₁₅N₃S
• 分子量: 233.337
• InChiKey: WAGAPELAEGWZMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硫代吗啉 、 2-(2-苯基肼基)乙醛 以 甲苯 为溶剂， 反应 3.0h， 以48%的产率得到1-phenylazo-2-(4-thiomorpholino)ethene
  参考文献：
  名称：

  Antimicrobial and cytotoxic arylazoenamines. Part III: Antiviral activity of selected classes of arylazoenamines

  摘要：

  Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses.The most commonly affected viruses were, in decreasing order, CVB-2, RSV, BVDV, YFV, and Sb-1; the remaining viruses were either not affected (HIV-1, VSV, and VV) or susceptible only to a very few compounds (Reo-1 and HSV-1).Thirty-five compounds exhibited high activity, with EC50 in the range 0.8-10 mu M, and other 28 compounds had EC50 between 11 and 30 mu M, thus indicating that the arylazoenamine molecular pattern is an interesting novel pharmacophore for antiviral agents against ssRNA viruses. Moreover, some compounds (as 28, 32, 42, and 53) appear of high interest, being devoid of toxicity on the human MT-4 cells (CC50 > 100 mu M).A ligand-based computational approach was employed to identify highly predictive pharmacophore models for the most frequently affected viruses CVB-2, RSV, and BVDV. These models should allow the design of second generation of more potent inhibitors of these human and veterinary pathogens. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.028

文献信息

• Antimicrobial and cytotoxic arylazoenamines. Part III: Antiviral activity of selected classes of arylazoenamines
  作者：Michele Tonelli、Vito Boido、Caterina Canu、Anna Sparatore、Fabio Sparatore、Maria Silvia Paneni、Maurizio Fermeglia、Sabrina Pricl、Paolo La Colla、Laura Casula、Cristina Ibba、David Collu、Roberta Loddo

  DOI：10.1016/j.bmc.2008.08.028

  日期：2008.9

  Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses.The most commonly affected viruses were, in decreasing order, CVB-2, RSV, BVDV, YFV, and Sb-1; the remaining viruses were either not affected (HIV-1, VSV, and VV) or susceptible only to a very few compounds (Reo-1 and HSV-1).Thirty-five compounds exhibited high activity, with EC50 in the range 0.8-10 mu M, and other 28 compounds had EC50 between 11 and 30 mu M, thus indicating that the arylazoenamine molecular pattern is an interesting novel pharmacophore for antiviral agents against ssRNA viruses. Moreover, some compounds (as 28, 32, 42, and 53) appear of high interest, being devoid of toxicity on the human MT-4 cells (CC50 > 100 mu M).A ligand-based computational approach was employed to identify highly predictive pharmacophore models for the most frequently affected viruses CVB-2, RSV, and BVDV. These models should allow the design of second generation of more potent inhibitors of these human and veterinary pathogens. (C) 2008 Elsevier Ltd. All rights reserved.