4-nitro-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazo<4,5-g>quinazolin-8(1H,7H)-one | 130148-34-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 4-nitro-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazo<4,5-g>quinazolin-8(1H,7H)-one
• 英文别名: 4-nitro-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazo[4,5-g]quinazolin-8(1H,7H)-one；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-nitro-8-oxo-5H-imidazo[4,5-g]quinazolin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 130148-34-4
• 化学式: C₂₀H₁₉N₅O₁₀
• 分子量: 489.398
• InChiKey: METYXEABTBELQJ-LCPZFUNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  194.84
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-nitro-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazo<4,5-g>quinazolin-8(1H,7H)-one 在 sodium dithionite 、 水 作用下， 以 甲醇 为溶剂， 以42%的产率得到4-amino-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazo<4,5-g>quinazolin-8(1H,7H)-one
  参考文献：
  名称：

  Regioselective synthesis of imidazo[4,5-g]quinazoline quinone nucleosides and quinazoline amino nucleosides. Studies of their xanthine oxidase and purine nucleoside phosphorylase substrate activity

  摘要：

  The regioselective synthesis of 3-ribofuranosylimidazo[4,5-g]quinazoline-4,8-9(3H,7H)-trione (1) (benzoquinone-stretched-out inosine) and 8-(ribofuranosylamino)quinaozlin-4(3G)-one (2) was carried out in conjunction with the design of reductive alkylating nuclosides and new purine nucleoside mimics, respectively. The preparation of 1 was carried out by regioselective ribosylation of 4-nitroimidazo[4,5-g]quinazolin-8(3H,7H)-one (3) followed by nitro group reduction, Fremy oxidation, and deacetylation. Regiocontrol of ribosylation has steric origions: the 4-nitro group of 3 directs silylation to the N(1) position, which results in ribosylation exclusively at the N(3) position under Vorbruggen reaction conditions. Regiocontrol during the preparation of 2 was possible by generating a stabilized ribofuranosyl carbocation, which selectively reacts with the amine group of the base. Nucleoside 1 is a purine-like quinone by virtue of its oxidation by xanthine oxidase. The potential inosine mimic 2 does not undergo phosphorolysis by purine nucleoside phosphorylase (PNPase), but the base form (8-amino-quinazolin-4(3H)-one) does bind to the PNPase active site as tightly as hypoxanthine. Factors which contribute to this binding behavior are discussed.

  DOI：

  10.1021/jo00002a052
• 作为产物：
  描述：

  4-nitroimidazo<4,5-g>quinazolin-8(3H,7H)-one 在 四氯化锡 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 51.0h， 生成 4-nitro-1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-imidazo<4,5-g>quinazolin-8(1H,7H)-one
  参考文献：
  名称：

  Regioselective synthesis of imidazo[4,5-g]quinazoline quinone nucleosides and quinazoline amino nucleosides. Studies of their xanthine oxidase and purine nucleoside phosphorylase substrate activity

  摘要：

  The regioselective synthesis of 3-ribofuranosylimidazo[4,5-g]quinazoline-4,8-9(3H,7H)-trione (1) (benzoquinone-stretched-out inosine) and 8-(ribofuranosylamino)quinaozlin-4(3G)-one (2) was carried out in conjunction with the design of reductive alkylating nuclosides and new purine nucleoside mimics, respectively. The preparation of 1 was carried out by regioselective ribosylation of 4-nitroimidazo[4,5-g]quinazolin-8(3H,7H)-one (3) followed by nitro group reduction, Fremy oxidation, and deacetylation. Regiocontrol of ribosylation has steric origions: the 4-nitro group of 3 directs silylation to the N(1) position, which results in ribosylation exclusively at the N(3) position under Vorbruggen reaction conditions. Regiocontrol during the preparation of 2 was possible by generating a stabilized ribofuranosyl carbocation, which selectively reacts with the amine group of the base. Nucleoside 1 is a purine-like quinone by virtue of its oxidation by xanthine oxidase. The potential inosine mimic 2 does not undergo phosphorolysis by purine nucleoside phosphorylase (PNPase), but the base form (8-amino-quinazolin-4(3H)-one) does bind to the PNPase active site as tightly as hypoxanthine. Factors which contribute to this binding behavior are discussed.

  DOI：

  10.1021/jo00002a052

文献信息

• OHARA, DEMPCY ROBERT;SKIBO, EDWARD B., J. ORG. CHEM., 56,(1991) N, C. 776-785
  作者：OHARA, DEMPCY ROBERT、SKIBO, EDWARD B.

  DOI：——

  日期：——