3-methylthio-5-phenyl-4-isothiazolecarbonitrile | 221006-20-8

• 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-methylthio-5-phenyl-4-isothiazolecarbonitrile
• 英文别名: 4-Isothiazolecarbonitrile, 3-(methylthio)-5-phenyl-；3-methylsulfanyl-5-phenyl-1,2-thiazole-4-carbonitrile
• CAS: 221006-20-8
• 化学式: C₁₁H₈N₂S₂
• 分子量: 232.33
• InChiKey: ZPMLIDDJACUALQ-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  90.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methylthio-5-phenyl-4-isothiazolecarbonitrile 在 盐酸 、 氢氧化钾 作用下， 以 乙二醇 为溶剂， 反应 60.0h， 生成 Methyl 3-methylsulfanyl-5-phenyl-isothiazole-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 、 碘甲烷 在 sodium sulfide 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 以74%的产率得到3-methylthio-5-phenyl-4-isothiazolecarbonitrile
  参考文献：
  名称：

  Synthesis and antiviral activity of a new series of 4-isothiazolecarbonitriles

  摘要：

  A series of 4-isothiazolecarbonitriles was synthesized and screened for in vitro antiviral activity. The effect of various substituents on the phenyl ring, as well as the substitution of the phenyl for other aromatic and heteroaromatic rings, was examined to establish the requirements for optimum activity. The most active member of the series, 3-methylthio-5-phenyl-4-isothiazolecarbonitrile, exhibited a high level of activity against enteroviruses polio 1 and ECHO 9. Preliminary studies on its mechanism of action indicated that this compound had an effect on an early event in the replication of poliovirus type 1. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)80007-2

文献信息

• Synthesis and antiviral activity of a new series of 4-isothiazolecarbonitriles
  作者：Christian C.C. Cutrí、Adriana Garozzo、Maria A. Siracusa、Maria C. Sarvá、Gianna Tempera、Ernesto Geremia、Maria R. Pinizzotto、Francesco Guerrera

  DOI：10.1016/s0968-0896(98)80007-2

  日期：1998.12

  A series of 4-isothiazolecarbonitriles was synthesized and screened for in vitro antiviral activity. The effect of various substituents on the phenyl ring, as well as the substitution of the phenyl for other aromatic and heteroaromatic rings, was examined to establish the requirements for optimum activity. The most active member of the series, 3-methylthio-5-phenyl-4-isothiazolecarbonitrile, exhibited a high level of activity against enteroviruses polio 1 and ECHO 9. Preliminary studies on its mechanism of action indicated that this compound had an effect on an early event in the replication of poliovirus type 1. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• 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.