9-((2S,3S,4R)-2,3,4,5-Tetrahydroxy-pentyl)-3,9-dihydro-purine-2,6-dione

• 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: 9-((2S,3S,4R)-2,3,4,5-Tetrahydroxy-pentyl)-3,9-dihydro-purine-2,6-dione
• 英文别名: 9-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-3H-purine-2,6-dione
• 化学式: C₁₀H₁₄N₄O₆
• 分子量: 286.244
• InChiKey: LCXLYUKTVSUQAL-BFHQHQDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酸二乙氧基甲酯 、 5-amino-6-D-ribitol-1-ylamino-1H-pyrimidine-2,4-dione; hydrochloride 在 水 作用下， 生成 9-((2S,3S,4R)-2,3,4,5-Tetrahydroxy-pentyl)-3,9-dihydro-purine-2,6-dione
  参考文献：
  名称：

  Synthesis of 2,6-Dioxo-(1 H ,3 H )-9- N -ribitylpurine and 2,6-Dioxo-(1 H ,3 H )-8-aza-9- N -ribitylpurine as inhibitors of lumazine synthase and riboflavin synthase

  摘要：

  2,6-Dioxo-(1H,3H)-9-N-ribitylpurine (6) and 2,6-dioxo-(1H,3H)-8-aza-9-N-ribitylpurin (7) have been synthesized and evaluated as inhibitors of lumazine synthase and riboflavin synthase. Reaction of 5-amino-6-ribityl-aminouracil hydrochloride (8) with diethoxymethyl acetate (9) afforded the purine 6, while diazotization of 8 afforded the 8-aza purine 7. Compounds 6 and 7 were evaluated against lumazine synthase of Bacillus subtilis and riboflavin synthase of Escherichia coli. Both 6 and 7 were better inhibitors of lumazine synthase than riboflavin synthase. The 8-azapurine 7 had a lower K-I (0.33 and 0.39 mM) than the purine 6 (0.47 and 0.54 mM) when evaluated with lumazine synthase and riboflavin synthase, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00013-3

文献信息

• Synthesis of 2,6-Dioxo-(1 H ,3 H )-9- N -ribitylpurine and 2,6-Dioxo-(1 H ,3 H )-8-aza-9- N -ribitylpurine as inhibitors of lumazine synthase and riboflavin synthase
  作者：Mark Cushman、Farahnaz Mavandadi、Karl Kugelbrey、Adelbert Bacher

  DOI：10.1016/s0968-0896(98)00013-3

  日期：1998.4

  2,6-Dioxo-(1H,3H)-9-N-ribitylpurine (6) and 2,6-dioxo-(1H,3H)-8-aza-9-N-ribitylpurin (7) have been synthesized and evaluated as inhibitors of lumazine synthase and riboflavin synthase. Reaction of 5-amino-6-ribityl-aminouracil hydrochloride (8) with diethoxymethyl acetate (9) afforded the purine 6, while diazotization of 8 afforded the 8-aza purine 7. Compounds 6 and 7 were evaluated against lumazine synthase of Bacillus subtilis and riboflavin synthase of Escherichia coli. Both 6 and 7 were better inhibitors of lumazine synthase than riboflavin synthase. The 8-azapurine 7 had a lower K-I (0.33 and 0.39 mM) than the purine 6 (0.47 and 0.54 mM) when evaluated with lumazine synthase and riboflavin synthase, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.