4-acetamido-3-cyano-1-<(2-acetoxyethoxy)methyl>pyrazolo<3,4-d>pyrimidine | 122949-69-3

• 英文名称: 4-acetamido-3-cyano-1-<(2-acetoxyethoxy)methyl>pyrazolo<3,4-d>pyrimidine
• 英文别名: 2-[(4-acetamido-3-cyanopyrazolo[3,4-d]pyrimidin-1-yl)methoxy]ethyl acetate
• CAS: 122949-69-3
• 化学式: C₁₃H₁₄N₆O₄
• 分子量: 318.292
• InChiKey: JQBXLXLCCUTLHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  132.02
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-acetamido-3-cyano-1-<(2-acetoxyethoxy)methyl>pyrazolo<3,4-d>pyrimidine 在 硫化氢 、 sodium methylate 、 三乙胺 、 mercury dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.8h， 生成 4-氨基-1-(2-羟基乙氧基甲基)吡唑并[3,4-d]嘧啶-3-腈
  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
• 作为产物：
  描述：

  4-氨基-1H-吡唑并[3,4-d]嘧啶-3-甲腈 在 吡啶 、 sodium hydride 作用下， 反应 2.58h， 生成 4-acetamido-3-cyano-1-<(2-acetoxyethoxy)methyl>pyrazolo<3,4-d>pyrimidine
  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：——