2-碘-6-氨基嘌呤 | 28128-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-碘-6-氨基嘌呤
• 英文名称: 2-iodoadenine
• 英文别名: 2-iodo-9H-purin-6-amine；2-iodo-7H-purin-6-amine
• CAS: 28128-26-9
• 化学式: C₅H₄IN₅
• mdl: MFCD08706404
• 分子量: 261.025
• InChiKey: HNVWCTKMOZAOJT-UHFFFAOYSA-N

物化性质

• 熔点：
  258-260 °C (decomp)
• 沸点：
  312°C
• 密度：
  2.92
• 闪点：
  143°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-碘-6-氨基嘌呤 在 copper(l) iodide 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium hydroxide monohydrate 、 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 potassium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 为溶剂， 反应 8.0h， 生成 cis-4-(6-amino-2-ethynyl-9H-purin-9-yl)-N-(3-methoxyphenyl)cyclohexanecarboxamide
  参考文献：
  名称：

  [EN] PURINE AND 3-DEAZAPURINE ANALOGUES AS CHOLINE KINASE INHIBITORS
  [FR] ANALOGUES DE PURINE ET DE 3-DÉAZAPURINE EN TANT QU'INHIBITEURS DE LA CHOLINE KINASE

  摘要：

  本发明提供了替代嘌呤和3-去氨基嘌呤类似物，可以调节胆碱激酶（ChoK）的活性。因此，本发明的化合物在治疗由改变的胆碱代谢引起的疾病方面是有用的，如癌症、细胞增殖紊乱、不同起源的传染病、免疫相关疾病和神经退行性疾病。本发明还提供了制备这些化合物的方法、包含这些化合物的药物组合物、以及利用包含这些化合物的药物组合物治疗疾病的方法。

  公开号：

  WO2018019681A1
• 作为产物：
  描述：

  2-碘-9-(四氢吡喃-2-基)腺嘌呤 在 水 、 copper dichloride 作用下， 以 乙醇 为溶剂， 以89%的产率得到2-碘-6-氨基嘌呤
  参考文献：
  名称：

  Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

  摘要：

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.057

文献信息

• [EN] PURINE AND 3-DEAZAPURINE ANALOGUES AS CHOLINE KINASE INHIBITORS<br/>[FR] ANALOGUES DE PURINE ET DE 3-DÉAZAPURINE EN TANT QU'INHIBITEURS DE LA CHOLINE KINASE
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2018019681A1

  公开（公告）日：2018-02-01

  There are provided substituted purine and 3-deazapurine analogues, which modulate the activity of Choline Kinase (ChoK). The compounds of this invention are therefore useful in treating diseases caused by an altered choline metabolism, such as cancer, cell proliferative disorders, infectious diseases of different origin, immune-related disorders and neurodegenerative disorders. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing pharmaceutical compositions comprising these compounds.

  本发明提供了替代嘌呤和3-去氨基嘌呤类似物，可以调节胆碱激酶（ChoK）的活性。因此，本发明的化合物在治疗由改变的胆碱代谢引起的疾病方面是有用的，如癌症、细胞增殖紊乱、不同起源的传染病、免疫相关疾病和神经退行性疾病。本发明还提供了制备这些化合物的方法、包含这些化合物的药物组合物、以及利用包含这些化合物的药物组合物治疗疾病的方法。
• Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides
  作者：Richard C. Foitzik、Shane M. Devine、Nicholas E. Hausler、Peter J. Scammells

  DOI：10.1016/j.tet.2009.08.057

  日期：2009.10

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.