6-decylsulfanyl-7H-purine | 6974-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-decylsulfanyl-7H-purine
• CAS: 6974-90-9
• 化学式: C₁₅H₂₄N₄S
• 分子量: 292.448
• InChiKey: IZEYPLNZOVRJBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴乙酸苯酯 、 6-decylsulfanyl-7H-purine 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以15%的产率得到Phenyl 2-(6-decylsulfanylpurin-9-yl)acetate
  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
• 作为产物：
  描述：

  1-氯癸烷 、 6-mercaptopurine 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以61%的产率得到6-decylsulfanyl-7H-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

• Synthetis of Potential Anticancer Agents. XVI. S-Substituted Derivatives of 6-Mercaptopurine^1a
  作者：Thomas P. Johnston、Lee B. Holum、John A. Montgomery

  DOI：10.1021/ja01556a026

  日期：1958.12
• Notes - Synthesis and Biological Activity of Some 6-(Substituted) thiopurines
  作者：Charles Skinner、Richard Ham、David Fitzgerald, Jr.、Robert Eskin、William Shive

  DOI：10.1021/jo01117a624

  日期：1956.11
• Hydrocarbon compositions containing heteroaromatic nitrogen compounds
  申请人：EXXON RESEARCH AND ENGINEERING COMPANY

  公开号：EP0069507B1

  公开（公告）日：1986-09-10
• US4367152A
  申请人：——

  公开号：US4367152A

  公开（公告）日：1983-01-04
• 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.

表征谱图