3-(2-Hydroxyethylsulfanyl)-5-phenyl-isothiazole-4-carbonitrile

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(2-Hydroxyethylsulfanyl)-5-phenyl-isothiazole-4-carbonitrile
• 英文别名: 3-(2-hydroxyethylsulfanyl)-5-phenyl-1,2-thiazole-4-carbonitrile
• 化学式: C₁₂H₁₀N₂OS₂
• 分子量: 262.356
• InChiKey: VTMLELQJTWZSTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴乙醇 、 3-氯-5-苯基异噻唑-4-甲腈 在 sodium sulfide 作用下， 生成 3-(2-Hydroxyethylsulfanyl)-5-phenyl-isothiazole-4-carbonitrile
  参考文献：
  名称：

  Synthesis of New 3,4,5-Trisubstituted Isothiazoles as Effective Inhibitory Agents of Enteroviruses

  摘要：

  The synthesis and evaluation of 3,4,5-trisubstituted isothiazoles as antiviral agents led to the discovery of several compounds effective in vitro against enteroviruses polio 1 and ECHO 9. Structure-activity relationship studies revealed that a short thioalkyl chain in the 3-position and a methyl ester group in the 4-position are the structural components that, to a large extent, contribute to the positive biological profile in terms of both selectivity and low cytotoxicity. Under one-step growth conditions, methyl 3-methylthio-5-phenyl-4-isothiazolecarboxilate caused the greatest activity if added within Ih after poliovirus adsorption. These data suggest interference with early events of viral replication. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00237-5

文献信息

• Synthesis of New 3,4,5-Trisubstituted Isothiazoles as Effective Inhibitory Agents of Enteroviruses
  作者：Christian C.C. Cutrı̀、Adriana Garozzo、Maria A. Siracusa、Maria C. Sarvà、Angelo Castro、Ernesto Geremia、Maria R. Pinizzotto、Francesco Guerrera

  DOI：10.1016/s0968-0896(98)00237-5

  日期：1999.2

  The synthesis and evaluation of 3,4,5-trisubstituted isothiazoles as antiviral agents led to the discovery of several compounds effective in vitro against enteroviruses polio 1 and ECHO 9. Structure-activity relationship studies revealed that a short thioalkyl chain in the 3-position and a methyl ester group in the 4-position are the structural components that, to a large extent, contribute to the positive biological profile in terms of both selectivity and low cytotoxicity. Under one-step growth conditions, methyl 3-methylthio-5-phenyl-4-isothiazolecarboxilate caused the greatest activity if added within Ih after poliovirus adsorption. These data suggest interference with early events of viral replication. (C) 1999 Elsevier Science Ltd. All rights reserved.