(RS)-5-((SR)-1-indol-3-yl-ethyl)-2-methylamino-thiazol-4-one | 61492-55-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (RS)-5-((SR)-1-indol-3-yl-ethyl)-2-methylamino-thiazol-4-one
• 英文别名: (+/-)-indolmycin thiazolone；(5R)-5-[(1S)-1-(1H-indol-3-yl)ethyl]-2-methylimino-1,3-thiazolidin-4-one
• CAS: 61492-55-5；61521-50-4；61521-51-5；103871-36-9
• 化学式: C₁₄H₁₅N₃OS
• 分子量: 273.359
• InChiKey: LNAVOACFLBACSL-QPUJVOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-5-((SR)-1-indol-3-yl-ethyl)-2-methylamino-thiazol-4-one 、 硫代氯甲酸乙酯 生成 3-[(RS)-1-((SR)-2-methylamino-4-oxo-4,5-dihydro-thiazol-5-yl)-ethyl]-indole-1-carbothioic acid S-ethyl ester
  参考文献：
  名称：

  Easily hydrolyzable, water-soluble derivatives of (.+-.)-.alpha.-5-[1-(indol-3-yl)ethyl]-2-methylamino-.DELTA.2-thiazolin-4-one, a novel antiviral compound

  摘要：

  The preparation of a series of indole N-acyl and N-carbamic esters of (+/-)-alpha-5-[1-(indol-3-yl)ethyl]-2-methylamino-delta2-thiazolin-4-one (1) is reported. These derivatives were synthesized as potential water-soluble precursors of the antiviral thiazolinone 1, for evaluation by intranasal administration against influenza and other respiratory infections caused by viruses. Salts of the basic carbamic esters (16--19) possess the required water solubility, undergo rapid hydrolysis and decarboxylation at pH values greater than 6, and have high activity against influenza A2 and Coxsackie B1 viruses in vitro. In influenza A2 infected ferrets a representative ester (16) reduced the severity and duration of disease symptoms and reduced nasal wash virus titres but caused local irritancy.

  DOI：

  10.1021/jm00188a013

文献信息

• Easily hydrolyzable, water-soluble derivatives of (.+-.)-.alpha.-5-[1-(indol-3-yl)ethyl]-2-methylamino-.DELTA.2-thiazolin-4-one, a novel antiviral compound
  作者：Michael R. Harnden、Stuart Bailey、Malcolm R. Boyd、J. Bruce Wilkinson、Nicholas D. Wright

  DOI：10.1021/jm00188a013

  日期：1979.2

  The preparation of a series of indole N-acyl and N-carbamic esters of (+/-)-alpha-5-[1-(indol-3-yl)ethyl]-2-methylamino-delta2-thiazolin-4-one (1) is reported. These derivatives were synthesized as potential water-soluble precursors of the antiviral thiazolinone 1, for evaluation by intranasal administration against influenza and other respiratory infections caused by viruses. Salts of the basic carbamic esters (16--19) possess the required water solubility, undergo rapid hydrolysis and decarboxylation at pH values greater than 6, and have high activity against influenza A2 and Coxsackie B1 viruses in vitro. In influenza A2 infected ferrets a representative ester (16) reduced the severity and duration of disease symptoms and reduced nasal wash virus titres but caused local irritancy.