N⁶-propargyladenine | 36412-34-7

• 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: N⁶-propargyladenine
• 英文别名: N-prop-2-ynyl-7H-purin-6-amine
• CAS: 36412-34-7
• 化学式: C₈H₇N₅
• 分子量: 173.177
• InChiKey: UYXSWMGZCLWMFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 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：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N⁶-propargyladenine 在 copper(l) iodide 、 叠氮基三甲基硅烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以4%的产率得到N-(2H-triazol-4-ylmethyl)-7H-purin-6-amine
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS USING THE SAME FOR TREATMENT OF NEURODEGENERATIVE AND MITOCHONDRIAL DISEASE
  [FR] COMPOSITIONS ET PROCEDES LES UTILISANT POUR LE TRAITEMENT DE MALADIE NEURODEGENERATIVE ET MITOCHONDRIALE

  摘要：

  本公开涉及部分化合物或其药用盐，用于治疗和/或预防神经退行性疾病和/或线粒体疾病，包括帕金森病和雷氏病。

  公开号：

  WO2015123365A1
• 作为产物：
  描述：

  6-N-2',3',5'-tri-O-tetraacetyladenosine 在 盐酸 、 氨 、 水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 76.0h， 生成 N⁶-propargyladenine
  参考文献：
  名称：

  Chemical modification of the plant isoprenoid cytokinin N6-isopentenyladenosine yields a selective inhibitor of human enterovirus 71 replication

  摘要：

  In this study, we demonstrate that N-6-isopentenyladenosine, which essentially is a plant cytokinin-like compound, exerts a potent and selective antiviral effect on the replication of human enterovirus 71 with an EC50 of 1.0 +/- 0.2 mu M and a selectivity index (SI) of 5.7. The synthesis of analogs with modification of the N-6-position did not result in a lower EC50 value. However, in particular with the synthesis of N6-(5hexene-2-yne-1-yl)adenosine (EC50 = 43 +/- 1.5 mu M), the selectivity index was significantly increased: because of a reduction in the adverse effect of this compound on the host cells, an SI > 101 could be calculated. With this study, we for the first time provide proof that a compound class that is based on the plant cytokinin skeleton offers an interesting starting point for the development of novel antivirals against mammalian viruses, in the present context in particular against enterovirus 71. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.048

文献信息

• Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction
  作者：Steven Fletcher

  DOI：10.1016/j.tetlet.2010.03.103

  日期：2010.6

  A novel synthetic route to N6-substitution of adenine is presented, employing the Mitsunobu reaction as the key step. A range of primary and secondary alcohols all coupled in very good to excellent yields within 30 min at 45 °C, offering a milder alternative to the traditional nucleophilic aromatic substitution of 6-chloropurine. The utility of this protocol is further demonstrated by its application

  以Mitsunobu反应为关键步骤，提出了一种新的合成途径来合成腺嘌呤的N 6-取代。在45°C下30分钟内，一系列伯醇和仲醇的收率都非常好，达到了极佳的水平，为传统的6-氯嘌呤亲核芳香族取代提供了温和的替代方法。通过将其应用于N 6，N 9-二取代的腺嘌呤的合成，包括有效的和选择性的A 1腺苷受体激动剂N 6-环戊基腺苷，进一步证明了该方案的实用性。
• Chemoenzymatic synthesis of cytokinins from nucleosides: ribose as a blocking group
  作者：Vladimir E. Oslovsky、Pavel N. Solyev、Konstantin M. Polyakov、Cyril S. Alexeev、Sergey N. Mikhailov

  DOI：10.1039/c8ob00223a

  日期：——

  Nucleoside phosphorylases are involved in the salvage pathways of nucleoside biosynthesis and catalyze the reversible reaction of a nucleobase with α-D-ribose-1-phosphate to yield a corresponding nucleoside and an inorganic phosphate. The equilibrium of these reactions is shifted towards nucleosides, especially in the case of purines. Purine nucleoside phosphorylase (PNP, EC 2.4.2.1) is widely used

  核苷磷酸化酶参与核苷生物合成的挽救途径，并催化核碱基与α - D-核糖-1-磷酸的可逆反应，生成相应的核苷和无机磷酸盐。这些反应的平衡向核苷转移，特别是在嘌呤的情况下。嘌呤核苷磷酸化酶（PNP，EC 2.4.2.1）在实验室和工业中广泛用于合成具有实际重要性的核苷。细菌PNP利用相对广泛的具有不同取代基的嘌呤形成相应的核苷，具有相对较宽的底物特异性。为了使反应朝相反的方向进行，我们使用了砷解作用而不是磷解作用。由于生成的α-的水解，该反应是不可逆的D-核糖-1-砷。结果，杂环碱以定量产率形成并且可以容易地分离。我们已经开发出一种新的细胞分裂素制备方法，该方法基于在PNP和Na 2 HAsO 4存在下酶解N 6取代的腺苷的N-糖苷键的方法。根据HPLC分析，转化以定量产率进行。在提出的策略中，核糖残基充当保护基。最终产品具有的ASO无污染4 3-已经检测到通过HPLC-HRMS; 已经提出了通过ESI-MS进行简单的砷分析检测。
• Compositions and methods using the same for treatment of neurodegenerative and mitochondrial disease
  申请人：Mitokinin, LLC

  公开号：US10167286B2

  公开（公告）日：2019-01-01

  The disclosure is directed to compounds and pharmaceutically acceptable salts thereof for the treatment and/or prevention of neurodegenerative and/or mitochondrial diseases, such as Parkinson's disease and Leigh's disease. The compounds and pharmaceutically acceptable salts thereof are of the class of nitrogenous bases, for example, pyrimidines, purines, pteridines and pharmaceutically acceptable salts thereof.

  本公开涉及用于治疗和/或预防神经退行性疾病和/或线粒体疾病（如帕金森病和利氏病）的化合物及其药学上可接受的盐。这些化合物及其药学上可接受的盐属于含氮碱类，例如嘧啶、嘌呤、蝶啶及其药学上可接受的盐。
• Compositions and methods of using the same for treatment of neurodegenerative and mitochondrial disease
  申请人：Mitokinin, Inc.

  公开号：US10851109B2

  公开（公告）日：2020-12-01

  The disclosure is directed to compounds and pharmaceutically acceptable salts thereof for the treatment and/or prevention of neurodegenerative and/or mitochondrial diseases, such as Parkinson's disease and Leigh's disease. The compounds and pharmaceutically acceptable salts thereof are of the class of nitrogenous bases, for example, pyrimidines, purines, pteridines, and pharmaceutically acceptable salts thereof.

  本公开涉及用于治疗和/或预防神经退行性疾病和/或线粒体疾病（如帕金森病和利氏病）的化合物及其药学上可接受的盐。这些化合物及其药学上可接受的盐属于含氮碱类，例如嘧啶、嘌呤、蝶啶及其药学上可接受的盐。
• COMPOSITIONS AND METHODS USING THE SAME FOR TREATMENT OF NEURODEGENERATIVE AND MITOCHONDRIAL DISEASE
  申请人：Mitokinin LLC

  公开号：EP3104706A1

  公开（公告）日：2016-12-21