6-chloro-3-methyl-9H-purin-3-ium chloride | 4776-20-9

• 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-chloro-3-methyl-9H-purin-3-ium chloride
• 英文别名: 6-chloro-3-methyl-7H-purin-3-ium;chloride
• CAS: 4776-20-9
• 化学式: C₆H₆ClN₄*Cl
• 分子量: 205.046
• InChiKey: BHVGHBADLDIIKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12
• 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：
  45.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-(3-Aminopropyloxy)-3,5-dibromophenethyl)-N-methylacetamide 、 6-chloro-3-methyl-9H-purin-3-ium chloride 在 N,N-二异丙基乙胺 作用下， 以 正丁醇 为溶剂， 反应 17.0h， 生成 aphrocallistin
  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-6-甲硫基嘌呤 在 氯 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以29%的产率得到6-chloro-3-methyl-9H-purin-3-ium chloride
  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

文献信息

• 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.