2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one | 127794-16-5

• 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: 2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one
• 英文别名: 2-Chloro-7-methyl-8-sulfanylidene-1,9-dihydropurin-6-one；2-chloro-7-methyl-8-sulfanylidene-1,9-dihydropurin-6-one
• CAS: 127794-16-5
• 化学式: C₆H₅ClN₄OS
• 分子量: 216.651
• InChiKey: ABBPZYDJWLBUSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 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：
  88.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one 在 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 6.5h， 生成 2-chloro-8,9-dihydro-7-methyl-9-(β-D-ribofuranosyl)-8-thioxopurin-6(1H)-one
  参考文献：
  名称：

  Synthesis and broad-spectrum antiviral activity of 7,8-dihydro-7-methyl-8-thioxoguanosine

  摘要：

  2,6,8-Trichloro-7-methylpurine (3) was converted to 2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one (5) by utilizing the difference in reactivity of the 2-, 6-, and 8-positions in the trichloropurine ring system to nucleophilic displacement. Compound 5 was subsequently glycosylated with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose according to the Vorbrüggen procedure to yield 2-chloro-8,9-dihydro-7-methyl-9-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosy l)-8- thioxopurin-6(1H)-one (6). Removal of the benzoyl protecting groups, followed by amination of 7 with liquid ammonia at 150 degrees C, gave 7,8-dihydro-7-methyl-8-thioxoguanosine (2). The structure of compound 2 was confirmed by X-ray crystallographic analysis. Compounds 1 (7,8-dihydro-7-methyl-8-oxoguanosine) and 2 were evaluated for activity in various animal virus infection models. Against banzi, Semliki Forest, and San Angelo viruses in mice, 2 was highly active when administered before virus inoculation.

  DOI：

  10.1021/jm00170a013
• 作为产物：
  描述：

  2,6,8-三氯-7-甲基嘌呤 在 sodium hydroxide 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one
  参考文献：
  名称：

  Synthesis and broad-spectrum antiviral activity of 7,8-dihydro-7-methyl-8-thioxoguanosine

  摘要：

  2,6,8-Trichloro-7-methylpurine (3) was converted to 2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one (5) by utilizing the difference in reactivity of the 2-, 6-, and 8-positions in the trichloropurine ring system to nucleophilic displacement. Compound 5 was subsequently glycosylated with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose according to the Vorbrüggen procedure to yield 2-chloro-8,9-dihydro-7-methyl-9-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosy l)-8- thioxopurin-6(1H)-one (6). Removal of the benzoyl protecting groups, followed by amination of 7 with liquid ammonia at 150 degrees C, gave 7,8-dihydro-7-methyl-8-thioxoguanosine (2). The structure of compound 2 was confirmed by X-ray crystallographic analysis. Compounds 1 (7,8-dihydro-7-methyl-8-oxoguanosine) and 2 were evaluated for activity in various animal virus infection models. Against banzi, Semliki Forest, and San Angelo viruses in mice, 2 was highly active when administered before virus inoculation.

  DOI：

  10.1021/jm00170a013

文献信息

• HENRY, ELIZABETH M.;KINI, GANESH D.;LARSON, STEVEN B.;ROBINS, ROLAND K.;A+, J. MED. CHEM., 33,(1990) N, C. 2127-2130
  作者：HENRY, ELIZABETH M.、KINI, GANESH D.、LARSON, STEVEN B.、ROBINS, ROLAND K.、A+

  DOI：——

  日期：——
• Synthesis and broad-spectrum antiviral activity of 7,8-dihydro-7-methyl-8-thioxoguanosine
  作者：Elizabeth M. Henry、Ganesh D. Kini、Steven B. Larson、Roland K. Robins、Hassan A. Alaghamandan、Donald F. Smee

  DOI：10.1021/jm00170a013

  日期：1990.8

  2,6,8-Trichloro-7-methylpurine (3) was converted to 2-chloro-8,9-dihydro-7-methyl-8-thioxopurin-6(1H)-one (5) by utilizing the difference in reactivity of the 2-, 6-, and 8-positions in the trichloropurine ring system to nucleophilic displacement. Compound 5 was subsequently glycosylated with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose according to the Vorbrüggen procedure to yield 2-chloro-8,9-dihydro-7-methyl-9-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosy l)-8- thioxopurin-6(1H)-one (6). Removal of the benzoyl protecting groups, followed by amination of 7 with liquid ammonia at 150 degrees C, gave 7,8-dihydro-7-methyl-8-thioxoguanosine (2). The structure of compound 2 was confirmed by X-ray crystallographic analysis. Compounds 1 (7,8-dihydro-7-methyl-8-oxoguanosine) and 2 were evaluated for activity in various animal virus infection models. Against banzi, Semliki Forest, and San Angelo viruses in mice, 2 was highly active when administered before virus inoculation.