9-allyl-2,6-dichloro-9H-purine | 157838-42-1

• 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: 9-allyl-2,6-dichloro-9H-purine
• 英文别名: 2,6-Dichloro-9-allylpurine；2,6-dichloro-9-prop-2-enylpurine
• CAS: 157838-42-1
• 化学式: C₈H₆Cl₂N₄
• 分子量: 229.068
• InChiKey: VWFGLDQYLYZLKV-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  328.6±52.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-allyl-2,6-dichloro-9H-purine 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 7.5h， 生成 1-[9-Prop-2-enyl-6-(prop-2-enylamino)purin-2-yl]piperidin-4-one
  参考文献：
  名称：

  New Purines and Purine Analogs as Modulators of Multidrug Resistance

  摘要：

  A series of 36 purine and purine analog derivatives have been synthesized and tested for their ability to modulate multidrug resistance in vitro (P388/VCR-20 and KB-A1 cells) and in vivo (P388/VCR leukemia). Compounds were compared to S9788, a triazine derivative which has already shown some activity during phase 1 clinical trials and also a limiting cardiovascular side effect possibly linked to its calcium channel affinity. The fact that active compounds increase adriamycin accumulation in the resistant KB-A1 cells, and not in the sensitive KB-3-1 cells, suggests they act predominantly by inhibiting the P-glycoprotein-catalyzed efflux of cytotoxic agents. No direct relation was found between the affinity for the phenylalkylamine binding site of the calcium channel and in vitro sensitization of resistant cells. In vivo, when administered po in association with vincristine (0.25 mg/kg), five compounds (3, 4, 9, 25, and 26), of very differing calcium channel affinities (K-i from 5 to 560 nM), fully restored (T/V greater than or equal to 1.4) the sensitivity of P388/VCR leukemia to vincristine.

  DOI：

  10.1021/jm960361i
• 作为产物：
  描述：

  3-溴丙烯 、 2,6-二氯嘌呤 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 以89%的产率得到9-allyl-2,6-dichloro-9H-purine
  参考文献：
  名称：

  微波辐射下水中不饱和核苷类似物的简便合成。

  摘要：

  开发了一种方便的微波辐射下水中不饱和核苷类似物区域选择性合成的方法。所有嘧啶和嘌呤核苷衍生物分别分别在N1和N9处烷基化，收率良好至极佳。另外，该系统可以耐受广泛的官能团，例如氯，溴，碘，烷基，氨基和羟基。更重要的是，反应规模可以扩大到50 mmol，这使该路线对工业应用具有吸引力。

  DOI：

  10.1080/15257770.2015.1114129

文献信息

• Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water
  作者：Ran Xia、Ming-Sheng Xie、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c3gc41658e

  日期：——

  A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66–95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。
• Microwave irradiated C6-functionalization of 6-chloropurine nucleosides with various mild nucleophiles under solvent-free conditions
  作者：Hai-Ming Guo、Peng-Yang Xin、Hong-Ying Niu、Dong-Chao Wang、Yi Jiang、Gui-Rong Qu

  DOI：10.1039/c0gc00517g

  日期：——

  purine nucleosides was developed via the direct nucleophilic substitution reaction of 6-chloropurine derivatives with various mild nucleophiles. The eco-friendly solvent-free process gave good to high isolated yields within a short reaction time (5 min) under microwave irradiated conditions.

  通过直接亲核试剂开发了一种有效的合成C6功能化嘌呤核苷的方法取代反应 的 6-氯嘌呤具有各种温和亲核试剂的衍生物。该环保型无溶剂工艺在微波辐射条件下，在较短的反应时间内（5分钟）即可获得很高的分离产率。
• [EN] SUBSTITUTED TRIAZINE AND PURINE COMPOUNDS, METHODS OF INHIBITING CRUZAIN AND RHODESAIN AND METHODS OF TREATING CHAGAS DISEASE AND AFRICAN TRYPANOSOMIASIS<br/>[FR] COMPOSÉS DE TRIAZINE ET DE PURINE SUBSTITUÉES, MÉTHODES D'INHIBITION DE CRUZAÏNE ET DE RHODÉSAÏNE ET MÉTHODES DE TRAITEMENT DE LA MALADIE DE CHAGAS ET DE LA TRYPANOSOMIASE AFRICAINE
  申请人：GOVERNMENT OF THE U S A AS REP

  公开号：WO2010059418A1

  公开（公告）日：2010-05-27

  The invention provides for novel triazine and purine compounds ( II ) that are useful for the treatment and prevention of mammalian protozoal diseases, including Af rican trypanosomiasis and Chagas disease.

  这项发明提供了一种新型的三嗪和嘌呤化合物（II），可用于治疗和预防哺乳动物原生动物疾病，包括非洲锥虫病和充血性心脏病。
• A2A adenosine receptor antagonists
  申请人：——

  公开号：US20030149060A1

  公开（公告）日：2003-08-07

  Disclosed are novel A 2A adenosine receptor antagonists, useful for treating various disease states, for example cardiovascular disorders, including tissue damage due to ischemia, CNS diseases, including Parkinson's disease, depression, and the like.

  揭示了一种新型A2A腺苷受体拮抗剂，可用于治疗各种疾病状态，例如心血管疾病，包括因缺血引起的组织损伤，中枢神经系统疾病，包括帕金森病、抑郁症等。
• Bicyclic pyrimidines
  申请人：Adir Et Compagnie

  公开号：US05508277A1

  公开（公告）日：1996-04-16

  Novel bicyclic pyrimidine compounds for use as drugs and having formula (I). Said novel compounds and physiologically tolerable salts thereof may be used in therapeutics, particularly for suppressing tumour cell resistance to antineoplastic agents. ##STR1##

  新型双环嘧啶化合物可用作药物，其化学式为（I）。这些新型化合物及其生理耐受盐可用于治疗，特别是用于抑制肿瘤细胞对抗肿瘤药物的耐药性。