cyanoethyl deazaguanine | 158608-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: cyanoethyl deazaguanine
• 英文别名: 2-amino-N-(2-cyanoethyl)-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidine-5-carboxamide
• CAS: 158608-23-2
• 化学式: C₁₀H₁₀N₆O₂
• 分子量: 246.228
• InChiKey: DEVGUEXPQOHYMW-UHFFFAOYSA-N

物化性质

• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyanoethyl deazaguanine 在 盐酸 、 甲醇 、 氨 作用下， 反应 25.0h， 生成 Echiguanine A
  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
• 作为产物：
  描述：

  2-pivaloylamino-4(3H)-oxo-5-iodo-7H-pyrrolo<2,3-d>pyrimidine 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 cyanoethyl deazaguanine
  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.
• Synthesis of echiguanine analogs and their ribofuranosyl glycosides that inhibit phosphatidylinositol 4-kinase
  作者：Yoshio Saito、Kazuo Umezawa、Kuniki Kato

  DOI：10.1016/s0960-894x(97)00122-4

  日期：1997.1

  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.
• Synthesis and Inhibitory Activity Against Phosphatidylinositol 4-Kinase of Echiguanine Analogs
  作者：Yoshio Saito、Kuniki Kato、Kazuo Umezawa

  DOI：10.1080/15257779908041550

  日期：1999.4

  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. The ethylamide 5 and the corresponding ribofuranosyl compound 11 inhibited PI 4-kinase with IC50 values of 0.02 and 2.4 mu g/ml, respectively.
• A short and efficient synthesis of echiguanines A and B: Potent inhibitors of phosphatidylinositol-4-kinase
  作者：Chuan Shih、Ying Hu

  DOI：10.1016/s0040-4039(00)76939-5

  日期：1994.7

  An efficient synthesis which utilizes a palladium catalyzed carbonylation reaction between 2-pivaloyl-7-iodo-7-deazaguanine and 3-aminopropionitrile as a key step was developed for the preparation of a new class of pyrrolopyrimidine based PI4-Kinase inhibitors: Echiguanines A and B.

  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．