6-amino-3,5-dihydro-3-(2-deoxy-α-D-erythro-pentofuranosyl)imidazo<4,5-c>pyridin-4-one | 83587-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 6-amino-3,5-dihydro-3-(2-deoxy-α-D-erythro-pentofuranosyl)imidazo<4,5-c>pyridin-4-one
• 英文别名: 6-amino-3-(2'-deoxy-α-D-ribofuranosyl)imidazo<4,5-c>pyridin-4(5H)-one；4H-Imidazo(4,5-c)pyridin-4-one, 6-amino-3-(2-deoxy-alpha-D-erythro-pentofuranosyl)-3,5-dihydro-；6-amino-3-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5H-imidazo[4,5-c]pyridin-4-one
• CAS: 83587-64-8
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.257
• InChiKey: OMSOWQIWKOMDDW-OOZYFLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(氰基甲基)-1H-咪唑-5-羧酸甲酯 在 ammonium sulfate 、 氨 、 四氯化锡 、 sodium carbonate 、 六甲基二硅氮烷 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 6-amino-3,5-dihydro-3-(2-deoxy-α-D-erythro-pentofuranosyl)imidazo<4,5-c>pyridin-4-one
  参考文献：
  名称：

  Syntheses and antitumor activity of 2-deoxyribofuranosides of 3-deazaguanine

  摘要：

  Synthesis of 2-deoxyribofuranosides of 3-deazaguanine (IX-XII) has been achieved by a base-catalyzed ring closure of appropriate 2-deoxyribofuranosides of methyl 5(4)-(cyanomethyl)imidazole-4(5)-carboxalate (IV-VII). The separation of isomers and anomers were accomplished by column chromatography and HPLC. The site of glycosidic linkage and the anomeric configurations were established on the basis of C-13 and proton magnetic resonance spectroscopy, as well as UV absorption characteristics. Preliminary results of the antitumor activity of these derivatives, in vitro and in vivo, are described.

  DOI：

  10.1021/jm00356a034

文献信息

• Synthesis and antiviral/antitumor activities of certain 3-deazaguanine nucleosides and nucleotides
  作者：Ganapathi R. Revankar、Pranab K. Gupta、Alexander D. Adams、N. Kent Dalley、Patricia A. McKernan、P. Dan Cook、Peter G. Canonico、Roland K. Robins

  DOI：10.1021/jm00377a002

  日期：1984.11

  3-deazaguanosine (2) has been developed by reacting methyl 5(4)-(cyanomethyl) imidazole-4(5)-carboxylate (4) and 5-(cyanomethyl)-1- (2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazole-4-carboxylate (6), respectively, with hydrazine. The 3-deazaguanosine 3',5'-cyclic phosphate (13) was prepared from 5-(cyanomethyl)-1-beta-D-ribofuranosyl-imidazole-4-carboxamide 5'-phosphate. Glycosylation of the trimethylsilyl 4

  通过使5（4）-（氰基甲基）咪唑-4（5）-羧酸甲酯反应，开发了一种制备抗病毒和抗肿瘤药3-deazaguanine（1）及其代谢物3-deazaguanosine（2）的新方法。 4）和5-（氰基甲基）-1-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）咪唑-4-羧酸酯（6）与肼。由5-（氰基甲基）-1-β-D-呋喃呋喃糖基-咪唑-4-羧酰胺5'-磷酸制备3-脱氮鸟苷3'，5'-环状磷酸酯（13）。在三甲基甲硅烷基三氟甲磺酸酯存在下，用1-O-甲基-2-脱氧-3,5-二-Op-甲苯甲酰基-D-呋喃呋喃糖将三甲基甲硅烷基4糖基化，得到相应的N-1和N-3糖基衍生物，其中α-配置（18和20）作为主要产品，以及少量的β-端基异构体（19和21）。然而，4的钠盐与1-氯-2-脱氧-3,5-二-Op-甲苯甲酰-α-D-赤型五氟呋喃糖（17）的糖基化反应仅产生良好的β-端基异构体（19和2