3-Ethylsulfanyl-5-phenyl-isothiazole-4-carboxylic acid | 223440-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Ethylsulfanyl-5-phenyl-isothiazole-4-carboxylic acid
• CAS: 223440-21-9
• 化学式: C₁₂H₁₁NO₂S₂
• 分子量: 265.357
• InChiKey: QLZHYICWHWHEPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-Ethylsulfanyl-5-phenyl-isothiazole-4-carboxylic acid 在 盐酸 作用下， 反应 12.0h， 以59%的产率得到Methyl 3-ethylsulfanyl-5-phenyl-1,2-thiazole-4-carboxylate
  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
• 作为产物：
  描述：

  3-氯-5-苯基异噻唑-4-甲腈 在 sodium sulfide 、 氢氧化钾 作用下， 以 乙二醇 为溶剂， 反应 63.0h， 生成 3-Ethylsulfanyl-5-phenyl-isothiazole-4-carboxylic acid
  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