2-chloro-6-((4-methoxyphenyl)thio)-9H-purine | 646510-31-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-chloro-6-((4-methoxyphenyl)thio)-9H-purine
• 英文别名: 2-chloro-6-[(4-methoxyphenyl)thio]purine；2-chloro-6-(4-methoxyphenyl)sulfanyl-7H-purine
• CAS: 646510-31-8
• 化学式: C₁₂H₉ClN₄OS
• mdl: MFCD27285858
• 分子量: 292.749
• InChiKey: QFNRVTXFPYFRII-UHFFFAOYSA-N

物化性质

• 熔点：
  260-263 °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

• 作为产物：
  描述：

  4-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95%的产率得到2-chloro-6-((4-methoxyphenyl)thio)-9H-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

• HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines
  作者：Yuvraj B. Bhujabal、Kamlesh S. Vadagaonkar、Aniket Gholap、Yogesh S. Sanghvi、Rambabu Dandela、Anant R. Kapdi

  DOI：10.1021/acs.joc.9b02371

  日期：2019.12.6

  A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.
• Copper Catalyzed Three-Component Ullmann C–S Coupling in PEG for the Synthesis of 6-Aryl/alkylthio-purines
  作者：Panpan Zhang、Yunfang Liu、Xulian Li、Geling Siri、Jieyuan Wang、Zhen Li、Yajun Jian、Ziwei Gao

  DOI：10.1021/acs.joc.3c02116

  日期：2024.2.16