4-氨基-1-[(2-羟基乙氧基)甲基]-1H-吡唑并[3,4-d]嘧啶-3-甲酰胺 | 122949-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-氨基-1-[(2-羟基乙氧基)甲基]-1H-吡唑并[3,4-d]嘧啶-3-甲酰胺
• 英文名称: 4-amino-1-<(2-hydroxyethoxy)methyl>pyrazolo<3,4-d>pyrimidine-3-carboxamide
• 英文别名: 1H-Pyrazolo(3,4-d)pyrimidine-3-carboxamide, 4-amino-1-((2-hydroxyethoxy)methyl)-；4-amino-1-(2-hydroxyethoxymethyl)pyrazolo[3,4-d]pyrimidine-3-carboxamide
• CAS: 122949-67-1
• 化学式: C₉H₁₂N₆O₃
• 分子量: 252.233
• InChiKey: NMZGBZABPKSEDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氨基-1H-吡唑并[3,4-d]嘧啶-3-甲腈 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 4-氨基-1-[(2-羟基乙氧基)甲基]-1H-吡唑并[3,4-d]嘧啶-3-甲酰胺
  参考文献：
  名称：

  Synthesis and antiviral activity of some 7-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine analogs of sangivamycin and toyocamycin

  摘要：

  The sodium salt of 4-amino-3-cyanopyrazolo[3,4-d]pyrimidine (1) was condensed with (2-acetoxyethoxy)methyl bromide (2) to provide the corresponding protected acyclic nucleoside, 4-amino-3-cyano-1-[(2-acetoxyethoxy)methyl]-pyrazolo[3,4-d]pyrimid ine (3). Treatment of 3 with sodium methoxide in methanol provided a good yield of methyl 4-amino-1-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine-3- formimidate (4). Treatment of the imidate (4) with sodium hydrogen sulfide gave the thiocarboxamide derivative 5. Aqueous base transformed 4 into 4-amino-1-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine-3- carboxamide (6) in good yield. Treatment of 5 with mercuric chloride furnished the toyocamycin analogue 7. Evaluation of compounds 1, 3-7 revealed that only the heterocycle (1) and the thiocarboxamide acyclic nucleoside (5) were active. Compound 5 was the more potent with activity against human cytomegalovirus and herpes simplex virus type 1.

  DOI：

  10.1021/jm00169a027

文献信息

• SAXENA, NAVEEN K.;COLEMAN, LISA A.;DRACH, JOHN C.;TOWNSEND, LEROY B., J. MED. CHEM., 33,(1990) N, C. 1980-1983
  作者：SAXENA, NAVEEN K.、COLEMAN, LISA A.、DRACH, JOHN C.、TOWNSEND, LEROY B.

  DOI：——

  日期：——
• Synthesis and antiviral activity of some 7-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine analogs of sangivamycin and toyocamycin
  作者：Naveen K. Saxena、Lisa A. Coleman、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jm00169a027

  日期：1990.7

  The sodium salt of 4-amino-3-cyanopyrazolo[3,4-d]pyrimidine (1) was condensed with (2-acetoxyethoxy)methyl bromide (2) to provide the corresponding protected acyclic nucleoside, 4-amino-3-cyano-1-[(2-acetoxyethoxy)methyl]-pyrazolo[3,4-d]pyrimid ine (3). Treatment of 3 with sodium methoxide in methanol provided a good yield of methyl 4-amino-1-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine-3- formimidate (4). Treatment of the imidate (4) with sodium hydrogen sulfide gave the thiocarboxamide derivative 5. Aqueous base transformed 4 into 4-amino-1-[(2-hydroxyethoxy)methyl]pyrazolo[3,4-d]pyrimidine-3- carboxamide (6) in good yield. Treatment of 5 with mercuric chloride furnished the toyocamycin analogue 7. Evaluation of compounds 1, 3-7 revealed that only the heterocycle (1) and the thiocarboxamide acyclic nucleoside (5) were active. Compound 5 was the more potent with activity against human cytomegalovirus and herpes simplex virus type 1.