3-甲基-3H-嘌呤-6(9H)-硫酮 | 1006-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 3-甲基-3H-嘌呤-6(9H)-硫酮
• 中文别名: 3,9-二氢-3-甲基-6H-嘌呤-6-硫酮；3-甲基-3,7-二氢-6H-嘌呤-6-硫酮
• 英文名称: 3-Methyl-6-thiohypoxanthin
• 英文别名: 3-Methyl-purin-6-thion；3-Methyl-6-mercaptopurin；3-Methyl-6-purinthion；6-Thioxo-3-methyl-purin；3-methyl-3,7(9)-dihydro-purine-6-thione；3-methyl-3H-purine-6(9H)-thione；3-Methylhypothioxanthin；3-Methyl-6-thiopurin；3-methyl-7H-purine-6-thione
• CAS: 1006-12-8
• 化学式: C₆H₆N₄S
• 分子量: 166.206
• InChiKey: AYDCZHIGNMCFPK-UHFFFAOYSA-N

物化性质

• 熔点：
  322-323 °C (decomp)
• 沸点：
  453.7±37.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-甲基-3H-嘌呤-6(9H)-硫酮 、 碘甲烷 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以61%的产率得到3-甲基-6-甲硫基嘌呤
  参考文献：
  名称：

  Isolation, Synthesis, and Biological Activity of Aphrocallistin, an Adenine-Substituted Bromotyramine Metabolite from the Hexactinellida Sponge Aphrocallistes beatrix

  摘要：

  A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed through a convergent, modular total synthetic route that is amenable toward future analogue preparation. Aphrocallistin inhibits the growth of a panel of human tumor cell lines with IC50 values ranging from 7.5 to > 100 mu M and has been shown to induce G1 cell cycle arrest in the PANC-1 pancreatic carcinoma cell line. Aphrocallistin has been fully characterized in the NCI cancer cell line panel and has undergone in vitro ADME pharmacological profiling.

  DOI：

  10.1021/np900183v
• 作为产物：
  描述：

  3-甲基-3H- 嘌呤-6(9H)-酮 在 吡啶 、 tetraphosphorus decasulfide 作用下， 生成 3-甲基-3H-嘌呤-6(9H)-硫酮
  参考文献：
  名称：

  Elion, 1957, p. 39,41

  摘要：

  DOI：

文献信息

• Elion, 1957, p. 39,41
  作者：Elion

  DOI：——

  日期：——
• Isolation, Synthesis, and Biological Activity of Aphrocallistin, an Adenine-Substituted Bromotyramine Metabolite from the Hexactinellida Sponge <i>Aphrocallistes beatrix</i>
  作者：Amy E. Wright、Gregory P. Roth、Jennifer K. Hoffman、Daniela B. Divlianska、Diana Pechter、Susan H. Sennett、Esther A. Guzmán、Patricia Linley、Peter J. McCarthy、Tara P. Pitts、Shirley A. Pomponi、John K. Reed

  DOI：10.1021/np900183v

  日期：2009.6.26

  A new adenine-substituted bromotyrosine-derived metabolite designated as aphrocallistin (1) has been isolated from the deep-water Hexactinellida sponge Aphrocallistes beatrix. Its structure was elucidated on the basis of spectral data and confirmed through a convergent, modular total synthetic route that is amenable toward future analogue preparation. Aphrocallistin inhibits the growth of a panel of human tumor cell lines with IC50 values ranging from 7.5 to > 100 mu M and has been shown to induce G1 cell cycle arrest in the PANC-1 pancreatic carcinoma cell line. Aphrocallistin has been fully characterized in the NCI cancer cell line panel and has undergone in vitro ADME pharmacological profiling.