2-氨基-N-(3-氨基丙基)-4-氧代-1,7-二氢吡咯并[4,5-e]嘧啶-5-甲酰胺 | 137319-26-7

• 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: 2-氨基-N-(3-氨基丙基)-4-氧代-1,7-二氢吡咯并[4,5-e]嘧啶-5-甲酰胺
• 英文名称: Echiguanine B
• 英文别名: 2-amino-N-(3-aminopropyl)-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidine-5-carboxamide
• CAS: 137319-26-7
• 化学式: C₁₀H₁₄N₆O₂
• 分子量: 250.26
• InChiKey: VJLKKBXETQVDAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氨基亚氨基甲烷磺酸 、 2-氨基-N-(3-氨基丙基)-4-氧代-1,7-二氢吡咯并[4,5-e]嘧啶-5-甲酰胺 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 5.0h， 以64%的产率得到2-amino-N-[3-(diaminomethylideneamino)propyl]-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidine-5-carboxamide
  参考文献：
  名称：

  Synthesis of echiguanine analogs and their ribofuranosyl glycosides that inhibit phosphatidylinositol 4-kinase

  摘要：

  N-carboxamide-substituted 7-deazaguanine-7-carboxamides and their ribofuranosyl compounds have been synthesized as echiguanine derivatives, and evaluated for inhibition of phosphatidylinositol (PI) Q-kinase. The ethylamide derivative and the corresponding ribofuranosyl compound inhibited PI 4-kinase with IC50 values of 0.02 and 2.4 mu g/ml, respectively. The latter was suggested to also inhibit the enzyme in cultured human epidermoid carcinoma cells. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00122-4
• 作为产物：
  描述：

  2-pivaloylamino-4(3H)-oxo-5-iodo-7H-pyrrolo<2,3-d>pyrimidine 在 platinum(IV) oxide 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 氨 、 氢气 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 2-氨基-N-(3-氨基丙基)-4-氧代-1,7-二氢吡咯并[4,5-e]嘧啶-5-甲酰胺
  参考文献：
  名称：

  短而有效的鸟嘌呤A和B的合成：磷脂酰肌醇4激酶的有效抑制剂

  摘要：

  开发了一种有效的合成方法，该方法利用2-新戊酰基-7-碘-7-脱氮鸟嘌呤和3-氨基丙腈之间的钯催化的羰基化反应作为关键步骤，用于制备新型的基于吡咯并嘧啶的PI4-激酶抑制剂：Echiguanines A和B．

  DOI：

  10.1016/s0040-4039(00)76939-5

文献信息

• Synthesis and structure-activity relationship of ribofuranosyl echiguanine analogs as inhibitors of phosphatidylinositol 4-kinase
  作者：Yoshio Saito、Kuniki Kato、Kazuo Umezawa

  DOI：10.1016/s0040-4020(98)00143-4

  日期：1998.4

  N-Substituted-2-amino-4(3H)-7H-oxopyrrolo[2,3-d]pyrimidine-5-carboxamides and their ribofuranosyl and 2',3'-dideoxyribofuranosyl derivatives were prepared as membrane permeable echiguanine analogs and tested for their ability to inhibit phosphatidylinositol (PI) 4-kinase. Compounds 5 and 6 were found to inhibit the enzyme approximately at the same level as echiguanines A and B. It is noteworthy that ribofuranosides 18, 19, and 20 and dideoxyribofuranoside 29 effectively inhibited PI 4-kinase. Thus, the terminal amide and related structures may be preferable for inhibition of the enzyme in echiguanine analogs with or without ribofuranoside. (C) 1998 Elsevier Science Ltd. All rights reserved.