pyridine-2-carbothioic acid O-methyl ester | 79639-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridine-2-carbothioic acid O-methyl ester
• 英文别名: 2-pyridinecarbothioic acid O-methyl ester；methyl pyridine-2-carbothioate；Methyl 2-pyridinecarbothioate；O-methyl pyridine-2-carbothioate
• CAS: 79639-79-5
• 化学式: C₇H₇NOS
• 分子量: 153.205
• InChiKey: VWGRYQLWMOTTJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pyridine-2-carbothioic acid O-methyl ester 、 丙二腈 、 碘甲烷 在 sodium ethanolate 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以48%的产率得到3-Methylsulfanyl-5-pyridin-2-yl-isothiazole-4-carbonitrile
  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
• 作为产物：
  描述：

  2-吡啶甲酸甲酯 在 劳森试剂 作用下， 生成 pyridine-2-carbothioic acid O-methyl ester
  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

• Influence of 3‐Thio Substituents on Benzylidene‐Directed Mannosylation. Isolation of a Bridged Pyridinium Ion and Effects of 3‐ <i>O</i> ‐Picolyl and 3‐ <i>S</i> ‐Picolyl Esters
  作者：Timothy F. McMillan、David Crich

  DOI：10.1002/ejoc.202200320

  日期：2022.5.25

  influence of substitution of oxygen for sulfur at the 3-position of 4,6-O-benzylidene-protected mannopyranosyl thioglycosides shows considerable protecting group-dependent variation. Notably, a 3-S-picolyl ester is α-directing, which contrasts with the β-directing effect of the corresponding 3-O-picolyl system. Activation of 3-S-picolinyl substituted system leads to the isolation of a stable seven-membered

  氧取代 4,6- O-亚苄基保护的吡喃甘露糖基硫代糖苷 3 位硫的影响显示出相当大的保护基依赖性变化。值得注意的是，3- S-甲基吡啶酯是 α-导向的，这与相应的 3- O-甲基吡啶基系统的 β-导向作用形成对比。3- S-甲基吡啶基取代系统的活化导致稳定的七元桥联双环吡啶鎓离子的分离。
• Budzikiewicz, H.; Lange, E.; Ockels, W., Phosphorus and Sulfur and the Related Elements, 1981, vol. 11, p. 33 - 46
  作者：Budzikiewicz, H.、Lange, E.、Ockels, W.

  DOI：——

  日期：——
• 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.