3-amino-1-methyl-6-(β-D-ribofuranosyl)pyrazolo<3,4-c>pyrazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-1-methyl-6-(β-D-ribofuranosyl)pyrazolo<3,4-c>pyrazole
• 英文别名: 3-amino-1-methyl-6-(β-D-ribofuranosyl)pyrazolo[3,4-c]pyrazole；(2R,3R,4S,5R)-2-(4-amino-6-methylpyrazolo[3,4-c]pyrazol-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₁₀H₁₅N₅O₄
• 分子量: 269.26
• InChiKey: ZODGDKBOZRZKAT-DAGMQNCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-methylamino-4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-1H-pyrazole 在 palladium hydroxide - carbon sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 paraffin 、 环己烯 为溶剂， 反应 21.5h， 生成 3-amino-1-methyl-6-(β-D-ribofuranosyl)pyrazolo<3,4-c>pyrazole
  参考文献：
  名称：

  Synthesis and Biological Activity of the Novel Adenosine Analogs; 3-Amino-6-(β-D-ribofuranosyl)pyrazolo[3,4-c]pyrazole and 3-Amino-1-methyl-6-(β-D-ribofuranosyl)pyrazolo[3,4-c]pyrazole

  摘要：

  Chemical modification of the 4-nitrile group in 5-amino-1-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole-4-carbonitrile (1) afforded 5-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole (3). The methylation of 3, via a three step procedure, gave 5-methylamino-4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole (3a). The mononuclear heterocyclic rearrangement (m.h.r) of 3 and 3a, provided a convenient route to the novel azapentalene adenosine analogs 3-amino-6-(beta-D-ribofuranosyl)pyrazolo[3,4-c]pyrazole (6) and 3-amino-1-methyl-6-(beta-D-ribofuranosyl)pyrazolo [3,4-c]pyrazole (6a), respectively. Compound 6 exhibited no cytotoxicity when screened in vitro against either mouse L1210 leukemic cells or human foreskin fibroblasts. Nor was it active against human cytomegalovirus. Compound 6a was designed and prepared to investigate the possibility that the lack of biological activity of 6 might be due to annular tautomerization limiting the ability of 6 to serve as a substrate for the activating enzyme adenosine kinase. This hypothesis was neither supported nor disproved by the results, as compound 6a was also inactive in both the antiproliferative and antiviral test systems.

  DOI：

  10.1080/15257779408013250

文献信息

• Synthesis and Biological Activity of the Novel Adenosine Analogs; 3-Amino-6-(β-D-ribofuranosyl)pyrazolo[3,4-<i>c</i>]pyrazole and 3-Amino-1-methyl-6-(β-D-ribofuranosyl)pyrazolo[3,4-<i>c</i>]pyrazole
  作者：David A. Berry、Linda L. Wotring、John C. Drach、Leroy B. Townsend

  DOI：10.1080/15257779408013250

  日期：1994.3

  Chemical modification of the 4-nitrile group in 5-amino-1-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole-4-carbonitrile (1) afforded 5-amino-4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole (3). The methylation of 3, via a three step procedure, gave 5-methylamino-4-(5-methyl-1,2,4-oxadiazol-3-yl)-1-(2,3,5-tri-O-benzyl-beta-D-ribofuranosyl)pyrazole (3a). The mononuclear heterocyclic rearrangement (m.h.r) of 3 and 3a, provided a convenient route to the novel azapentalene adenosine analogs 3-amino-6-(beta-D-ribofuranosyl)pyrazolo[3,4-c]pyrazole (6) and 3-amino-1-methyl-6-(beta-D-ribofuranosyl)pyrazolo [3,4-c]pyrazole (6a), respectively. Compound 6 exhibited no cytotoxicity when screened in vitro against either mouse L1210 leukemic cells or human foreskin fibroblasts. Nor was it active against human cytomegalovirus. Compound 6a was designed and prepared to investigate the possibility that the lack of biological activity of 6 might be due to annular tautomerization limiting the ability of 6 to serve as a substrate for the activating enzyme adenosine kinase. This hypothesis was neither supported nor disproved by the results, as compound 6a was also inactive in both the antiproliferative and antiviral test systems.