2-(prop-2-ynyl)amino-1,9-dihydro-purin-6-one | 1236152-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-(prop-2-ynyl)amino-1,9-dihydro-purin-6-one
• 英文别名: Propargyl-guanine；2-(prop-2-ynylamino)-1,7-dihydropurin-6-one
• CAS: 1236152-00-3
• 化学式: C₈H₇N₅O
• 分子量: 189.176
• InChiKey: YYNPDYZWLINKSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (6-chloro-9-trityl-9H-purin-2-yl)-(prop-2-ynyl)-amine 在 甲酸 作用下， 以 水 为溶剂， 反应 4.0h， 以97%的产率得到2-(prop-2-ynyl)amino-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions

  摘要：

  Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing interest in designer PNAs and G-quartets, simple and efficient synthetic routes to novel guanines would be of significant benefit. We herein report that, upon simple protection and/or activation step(s), the guanine precursor 2-amino-6-chloropurine is rendered an excellent substrate for Mitsunobu chemistry, furnishing, after subsequent hydrolytic dechlorination and appropriate deprotection step(s), the desired N9-mono-, N2-mono- or N2,N9-di-substituted guanines in excellent yields (>= 80%). Importantly, we demonstrate that N9-functionalization proceeds with very good N9/N7 regioselectivity and with complete inversion of stereochemistry. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.118

文献信息

• 一种N²取代鸟嘌呤类化合物的制备方法
  申请人：华东师范大学

  公开号：CN108794477A

  公开（公告）日：2018-11-13

  本发明公开了一种N 2 取代鸟嘌呤类化合物的制备方法，利用化合物I即2‑氨基‑6‑羟基嘌呤为起始原料，在催化剂作用下与二碳酸二叔丁酯发生亲核取代反应，得到化合物Ⅱ；化合物Ⅱ在强碱作用下，发生亲核取代反应，得到化合物Ⅲ；化合物Ⅲ在催化剂作用下与二碳酸二叔丁酯发生亲核取代反应，得到化合物Ⅳ；化合物Ⅳ在碱性条件下与卤代烃（苄溴、1‑碘正丁烷和炔丙基溴）发生亲核取代反应，得到化合物Ⅴ（R为苄基、正丁基和炔丙基）；化合物Ⅴ分别在酸性条件下发生水解反应，得到目标化合物Ⅵ（R为苄基、正丁基和炔丙基）即N 2 ‑取代鸟嘌呤。本发明只需五步合成就可得到目标产物，该方法条件易控、后处理简单、副反应少、收率高，符合工业化生产的要求。
• Substrates for o6-alkylguanina-dna alkyltransferase
  申请人：Kindermann Maik

  公开号：US20060024775A1

  公开（公告）日：2006-02-02

  The present invention relates to methods of transferring a label from novel substrates to O 6 -alkylguanine-DNA alkyltransferases (AGT) and O 6 -alkylguanine-DNA alkyltransferase fusion proteins, and to novel substrates suitable in such methods. Proteins of interest are incorporated into an AGT fusion protein, the AGT fusion protein is contacted with particular AGT substrates carrying a label, and the AGT fusion protein is detected and optionally further manipulated using the label in a system designed for recognising and/or handling the label. The particular AGT substrates used in the method of the invention are O 6 -substituted guanine derivatives or related nitrogen containing hydroxy-heterocycles and their sulfur analogs wherein the O 6 -substituent is an activated methyl derivative suitable for transfer from guanine or the corresponding heterocycle to AGT, and further carrying a label or a plurality of same or different labels. The invention relates also to the novel AGT substrates as such, to methods of manufacture of such novel substrates, and to intermediates useful in the synthesis of such novel AGT substrates.

  本发明涉及将标签从新型底物转移至O6-烷基鸟嘌呤-DNA烷基转移酶（AGT）和O6-烷基鸟嘌呤-DNA烷基转移酶融合蛋白质的方法，以及适用于这种方法的新型底物。感兴趣的蛋白质被并入AGT融合蛋白质中，AGT融合蛋白质与携带标签的特定AGT底物接触，并使用系统识别和/或处理标签来检测AGT融合蛋白质并可选地进一步操作。本发明中使用的特定AGT底物是O6取代鸟嘌呤衍生物或相关氮含杂环氢氧基化合物及其硫化物，其中O6取代基是适合从鸟嘌呤或相应杂环到AGT转移的活性甲基衍生物，并进一步携带一个标签或多个相同或不同的标签。本发明还涉及新型AGT底物本身，制造这种新型底物的方法，以及合成这种新型AGT底物的中间体。
• SUBSTRATES FOR O6-ALKYLGUANINE-DNA ALKYLTRANSFERASE
  申请人：ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL)

  公开号：EP1546371A1

  公开（公告）日：2005-06-29
• US7799524B2
  申请人：——

  公开号：US7799524B2

  公开（公告）日：2010-09-21
• [EN] SUBSTRATES FOR O<6>-ALKYLGUANINE-DNA ALKYLTRANSFERASE<br/>[FR] SUBSTRATS DE O<6>-ALKYLGUANINE-ADN ALKYLTRANSFERASE
  申请人：ECOLE POLYTECH

  公开号：WO2004031405A1

  公开（公告）日：2004-04-15

  The present invention relates to methods of transferring a label from novel substrates to O6-alkylguanine-DNA alkyltransferases (AGT) and O6-alkylguanine-DNA alkyltransferase fusion proteins, and to novel substrates suitable in such methods. Proteins of interest are incorporated into an AGT fusion protein, the AGT fusion protein is contacted with particular AGT substrates carrying a label, and the AGT fusion protein is detected and optionally further manipulated using the label in a system designed for recognising and/or handling the label. The particular AGT substrates used in the method of the invention are O6-substituted guanine derivatives or related nitrogen containing hydroxy-heterocycles and their sulfur analogs wherein the O6-substituent is an activated methyl derivative suitable for transfer from guanine or the corresponding heterocycle to AGT, and further carrying a label or a plurality of same or different labels. The invention relates also to the novel AGT substrates as such, to methods of manufacture of such novel substrates, and to intermediates useful in the synthesis of such novel AGT substrates.