7-[2,3,5-tri-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]imidazo[4,5-d][1,2,3]triazine-4-thione | 270065-14-0

• 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-tri-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]imidazo[4,5-d][1,2,3]triazine-4-thione
• 英文别名: 7-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1H-imidazo[4,5-d]triazine-4-thione
• CAS: 270065-14-0
• 化学式: C₂₇H₅₃N₅O₄SSi₃
• 分子量: 628.071
• InChiKey: RBYQUXFNFAXPSP-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 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：
  124
• 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-tri-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]imidazo[4,5-d][1,2,3]triazine-4-thione 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 4-methylthio-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：

  7-(2,3,5-Tris-O-(t-butyldimethylsilyl)-β-D-ribofyranosyl)imidazo<4,5-d>-v-triazin-4-one 在 吡啶 、 硫化氢 、 三氯氧磷 作用下， 反应 0.25h， 以42%的产率得到7-[2,3,5-tri-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]imidazo[4,5-d][1,2,3]triazine-4-thione
  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 4-Substituted Imidazo[4,5-<i>d</i>][1,2,3]triazine (2-Azapurine)nucleosides
  作者：Steven Krawczyk、Michael T. Migawa、John C. Drach、Leroy B. Townsend

  DOI：10.1080/15257770008032996

  日期：2000.1

  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.