7-(2,3,5-Tris-O-(t-butyldimethylsilyl)-β-D-ribofyranosyl)imidazo<4,5-d>-v-triazin-4-one | 138481-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2,3,5-Tris-O-(t-butyldimethylsilyl)-β-D-ribofyranosyl)imidazo<4,5-d>-v-triazin-4-one
• 英文别名: 7-[2,3,5-tri-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]imidazo[4,5-d][1,2,3]triazin-4-one；7-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3H-imidazo[4,5-d]triazin-4-one
• CAS: 138481-53-5
• 化学式: C₂₇H₅₃N₅O₅Si₃
• 分子量: 612.005
• InChiKey: VOCLFTKPIFQZKN-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(2,3,5-Tris-O-(t-butyldimethylsilyl)-β-D-ribofyranosyl)imidazo<4,5-d>-v-triazin-4-one 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.58h， 生成 4-methylamino-7-(β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine
  参考文献：
  名称：

  Synthesis of 4-Substituted Imidazo[4,5-d][1,2,3]triazine (2-Azapurine)nucleosides

  摘要：

  Several methods for functionalization of the 4-position of imidazo[4,5-d][1,2,3]triazin-4-one were investigated. These investigations were successful and led to the preparation of 4-amino, 4-triazol-1-yl, 4-methoxy, 4-methylthio, 4-methylamino, 4-thio, 4-nitrobenzyl, and 4-unsubstituted 9-(beta-D-ribofuranosyl)-imidazo-[4,5-d][1,2,3]triazine (2-azapurine ribosides). The 4-unsubstituted compound (19) was slightly active against HCMV in plaque and yield reduction experiments and was not cytotoxic at 100 mu M. The methylamino (15), hydrazino (16), and p-nitrobenzylthio (20) were inactive against HCMV but slightly cytotoxic. The thiomethyl-substituted analog (21) was the most active with activity comparable to ganciclovir but with greater cytotoxicity. We conclude that even though none of the tested compounds had antiviral activity superior to ganciclovir, the new synthetic methods will provide a route to more interesting compounds.

  DOI：

  10.1080/15257770008032996
• 作为产物：
  描述：

  2-azainosine 、 叔丁基二甲基氯硅烷 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到7-(2,3,5-Tris-O-(t-butyldimethylsilyl)-β-D-ribofyranosyl)imidazo<4,5-d>-v-triazin-4-one
  参考文献：
  名称：

  Synthesis of 4-Substituted Imidazo[4,5-d][1,2,3]triazine (2-Azapurine)nucleosides

  摘要：

  Several methods for functionalization of the 4-position of imidazo[4,5-d][1,2,3]triazin-4-one were investigated. These investigations were successful and led to the preparation of 4-amino, 4-triazol-1-yl, 4-methoxy, 4-methylthio, 4-methylamino, 4-thio, 4-nitrobenzyl, and 4-unsubstituted 9-(beta-D-ribofuranosyl)-imidazo-[4,5-d][1,2,3]triazine (2-azapurine ribosides). The 4-unsubstituted compound (19) was slightly active against HCMV in plaque and yield reduction experiments and was not cytotoxic at 100 mu M. The methylamino (15), hydrazino (16), and p-nitrobenzylthio (20) were inactive against HCMV but slightly cytotoxic. The thiomethyl-substituted analog (21) was the most active with activity comparable to ganciclovir but with greater cytotoxicity. We conclude that even though none of the tested compounds had antiviral activity superior to ganciclovir, the new synthetic methods will provide a route to more interesting compounds.

  DOI：

  10.1080/15257770008032996

文献信息

• Synthesis of a pyrido[1,2-a]purine nucleoside by a novel ring cleavage-annulation reaction of 3-β-D-ribofuranosylimidazo-[4,5-d]--triazin-4-one
  作者：Steven H. Krawczyk、Leroy B. Townsend

  DOI：10.1016/s0040-4039(00)93532-9

  日期：1991.10

  Treatment of 7-(2,3,5-tris-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one (1) with MnO2 in hot pyridine furnished 7-(2,3,5-tris-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl)pyrido[1,2-a]-purine (4). Treatment of 4 with tetra-n-butylammonium fluoride furnished the free nucleoside 5.

  的治疗7-（2,3,5-三- O-（叔丁基二甲基）-β-d-D-呋喃核糖基）咪唑并[4,5-d] -v三嗪-4-酮（1）与MnO的2在热吡啶提供7-（2,3,5-三-O-（叔丁基二甲基甲硅烷基）-β-D-呋喃呋喃糖基）吡啶[1,2-a]-嘌呤（4）。用四正丁基氟化铵处理4提供了游离核苷5。