7,8-二氢-7-甲基-8-噻吩基氧代鸟苷 | 127794-14-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 7,8-二氢-7-甲基-8-噻吩基氧代鸟苷
• 中文别名: 乙基3-甲基-3-(4-甲基戊-3-烯基)噁丙环-2-羧酸酯
• 英文名称: 7,8-dihydro-7-methyl-8-thioxoguanosine
• 英文别名: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-8-sulfanylidene-1H-purin-6-one
• CAS: 127794-14-3
• 化学式: C₁₁H₁₅N₅O₅S
• 分子量: 329.337
• InChiKey: RYCBQZRMWCNRMH-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,6,8-三氯-7-甲基嘌呤 在 sodium hydroxide 、 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 氨 、 sodium methylate 、 硫脲 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.5h， 生成 7,8-二氢-7-甲基-8-噻吩基氧代鸟苷
  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

• Amp-kinase agonists or adenosine pro-drugs as immuno-stimulating agents
  申请人：Leo Oberdan

  公开号：US20050002943A1

  公开（公告）日：2005-01-06

  The present invention relates to the use of AMP-activated protein kinase (AMP-kinase) agonists or adenosine pro-drugs as immune enhancing compounds, as adjuvants in a vaccine or as anti-inflammatory compounds. The invention further relates to a compositions, vaccines and products comprising an immune response eliciting molecule and an immune response enhancing compound, wherein said immune enhancing compound is chosen from the group of AMP-activated protein kinase (AMP-kinase) agonists or adenosine pro-drugs.

  本发明涉及 AMP 活化蛋白激酶（AMP-激酶）激动剂或腺苷原药作为免疫增强化合物、疫苗佐剂或消炎化合物的用途。本发明还涉及一种包含免疫应答激发分子和免疫应答增强化合物的组合物、疫苗和产品，其中所述免疫增强化合物选自 AMP 活化蛋白激酶（AMP-激酶）激动剂或腺苷原药组。
• 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：——
• Immunostimulating guanine dervatives, compositions and methods
  申请人：SCRIPPS CLINIC AND RESEARCH FOUNDATION

  公开号：EP0341065B1

  公开（公告）日：1994-07-27
• AMP-KINASE AGONISTS OR ADENOSINE PRO-DRUGS AS IMMUNO-STIMULATING AGENTS
  申请人：Université Libre de Bruxelles

  公开号：EP1492564A2

  公开（公告）日：2005-01-05
• US5011828A
  申请人：——

  公开号：US5011828A

  公开（公告）日：1991-04-30