4-氨基-1-(2-羟基乙氧基甲基)吡唑并[3,4-d]嘧啶-3-腈 | 122949-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 中文名称: 4-氨基-1-(2-羟基乙氧基甲基)吡唑并[3,4-d]嘧啶-3-腈
• 英文名称: 4-amino-3-cyano-1-<(2-hydroxyethoxy)methyl>pyrazolo<3,4-d>pyrimidine
• 英文别名: 1H-Pyrazolo(3,4-d)pyrimidine-3-carbonitrile, 4-amino-1-((2-hydroxyethoxy)methyl)-；4-amino-1-(2-hydroxyethoxymethyl)pyrazolo[3,4-d]pyrimidine-3-carbonitrile
• CAS: 122949-68-2
• 化学式: C₉H₁₀N₆O₂
• 分子量: 234.217
• InChiKey: SIKQODOYOJZCFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-氨基-1-(2-羟基乙氧基甲基)吡唑并[3,4-d]嘧啶-3-腈 、 氨基磺酰氯 、 calcium carbonate 以 N,N-二甲基甲酰胺 为溶剂， 以to provide sulfamic acid 2-((4-amino-3-cyano-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methoxy)ethyl ester的产率得到sulfamic acid 2-((4-amino-3-cyano-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methoxy)ethyl ester
  参考文献：
  名称：

  SULFAMOYL-CONTAINING DERIVATIVES AND USES THEREOF

  摘要：

  本文披露了含有磺酰胺的化合物，具有抑制与疾病相关的靶点（例如热休克蛋白90（HSP90））的作用，并且适用于治疗疾病，例如增殖性疾病，包括HSP90介导的疾病。还描述了制备和使用这些化合物的方法。

  公开号：

  US20080096903A1
• 作为产物：
  描述：

  4-氨基-1H-吡唑并[3,4-d]嘧啶-3-甲腈 在 吡啶 、 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 27.38h， 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

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：——
• [EN] SULFAMOYL-CONTAINING DERIVATIVES AND USES THEREOF<br/>[FR] Dérivés contenant un sulfamoyle et leurs utilisations
  申请人：WYETH CORP

  公开号：WO2008049105A2

  公开（公告）日：2008-04-24

  [EN] Sulfamoyl-containing compounds are disclosed, having utility as inhibitors of disease-related targets, such as Heat Shock Protein 90 (HSP90), and which are useful for treating disorders, e.g., proliferative disorders, including HSP90-mediated disorders. Methods for preparing and using the disclosed compounds are also described.
  [FR] La présente invention concerne des composés contenant un sulfamoyle, présentant une utilité en tant qu'inhibiteurs de cibles liées à des maladies, comme la protéine de choc thermique 90 (HSP90), et utiles dans le traitement de troubles, par exemple de troubles prolifératifs, incluant les troubles induits par la HSP90. L'invention concerne également des procédés de préparation et d'utilisation des composés présentés.
• SULFAMOYL-CONTAINING DERIVATIVES AND USES THEREOF
  申请人：Chen Jianxin

  公开号：US20080096903A1

  公开（公告）日：2008-04-24

  Sulfamoyl-containing compounds are disclosed, having utility as inhibitors of disease-related targets, such as Heat Shock Protein 90 (HSP90), and which are useful for treating disorders, e.g., proliferative disorders, including HSP90-mediated disorders. Methods for preparing and using the disclosed compounds are also described.

  披露了含有磺酰氨基的化合物，这些化合物可用作疾病相关靶点的抑制剂，例如热休克蛋白90（HSP90），并且可用于治疗疾病，例如增殖性疾病，包括HSP90介导的疾病。还描述了制备和使用所披露化合物的方法。
• 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.