4-acetamido-3-cyanopyrazolo[3,4-d]pyrimidine | 55559-48-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-acetamido-3-cyanopyrazolo[3,4-d]pyrimidine
• 英文别名: N-(3-cyano-2H-pyrazolo[3,4-d]pyrimidin-4-yl)acetamide
• CAS: 55559-48-3
• 化学式: C₈H₆N₆O
• 分子量: 202.175
• InChiKey: OXEMELLXPYSEMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetamido-3-cyanopyrazolo[3,4-d]pyrimidine 在 硫化氢 、 sodium methylate 、 sodium hydride 、 三乙胺 、 mercury dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.8h， 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 、 乙酸酐 在 吡啶 作用下， 反应 0.58h， 以40%的产率得到4-acetamido-3-cyanopyrazolo[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

• 7-Substituted nucleoside compounds
  申请人：The University of Utah

  公开号：US03962211A1

  公开（公告）日：1976-06-08

  Novel compounds of the formula ##SPC1## Wherein R is selected from the group consisting of carboxamidine, carboxylic acid, carboxamide, methyl formimidate, thiocarboxamide, carboxamidoxime, carboxamidrazone, and cyano. The compounds have been demonstrated to be useful by having a degree of antimetabolic activity.

  化合物的新颖结构如下所示：##SPC1## 其中R从以下组中选择：羧酰胺基、羧酸、羧酰胺、甲基甲酰胺基、硫代羧酰胺、羧酰胺肟、羧酰胺脲和氰基。这些化合物已经被证明具有一定的抗代谢活性。
• 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：——
• US3962211A
  申请人：——

  公开号：US3962211A

  公开（公告）日：1976-06-08
• 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.