2-chloro-6-[(2-methoxyphenyl)thio]purine | 646510-26-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-chloro-6-[(2-methoxyphenyl)thio]purine
• 英文别名: 2-chloro-6-(2-methoxyphenyl)sulfanyl-7H-purine
• CAS: 646510-26-1
• 化学式: C₁₂H₉ClN₄OS
• mdl: MFCD27718118
• 分子量: 292.749
• InChiKey: TWQRUJSYNRQEDT-UHFFFAOYSA-N

物化性质

• 熔点：
  190 °C
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-二氢呋喃 、 2-chloro-6-[(2-methoxyphenyl)thio]purine 在 L-proline triflate 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以75%的产率得到
  参考文献：
  名称：

  l-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers

  摘要：

  An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by L-ProT. The advantages of this protocol include good to excellent yield, mild reaction condition, and simple manipulation. A plausible mechanism for the transformation was given. (C) 2014 Jian-Jun Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.04.023
• 作为产物：
  描述：

  2-甲氧基苯硫酚 、 2,6-二氯嘌呤 在 potassium tert-butylate 作用下， 以 异丙醇 为溶剂， 以81%的产率得到2-chloro-6-[(2-methoxyphenyl)thio]purine
  参考文献：
  名称：

  Antimycobacterial Agents. 1. Thio Analogues of Purine

  摘要：

  Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 mug/mL respectively against the Mtb H(37)Rv strain. N-9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.

  DOI：

  10.1021/jm030389b

文献信息

• Antimycobacterial Agents. 1. Thio Analogues of Purine
  作者：Ashish K. Pathak、Vibha Pathak、Lainne E. Seitz、William J. Suling、Robert C. Reynolds

  DOI：10.1021/jm030389b

  日期：2004.1.1

  Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 mug/mL respectively against the Mtb H(37)Rv strain. N-9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.
• l-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers
  作者：Jian-Jun Li、Xing-Xing Gui

  DOI：10.1016/j.cclet.2014.04.023

  日期：2014.10

  An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by L-ProT. The advantages of this protocol include good to excellent yield, mild reaction condition, and simple manipulation. A plausible mechanism for the transformation was given. (C) 2014 Jian-Jun Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.