6-chloro-9-(2-phenylethyl)-9H-purine | 16833-25-3

• 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: 6-chloro-9-(2-phenylethyl)-9H-purine
• 英文别名: 6-chloro-9-phenethyl-9H-purine；9-β-Phenethyl-6-chlor-purin；6-Chlor-9-phenaethyl-purin；6-chloro-9-(2-phenylethyl)purine
• CAS: 16833-25-3
• 化学式: C₁₃H₁₁ClN₄
• 分子量: 258.71
• InChiKey: PVLKCPQYCKRELM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  6-chloro-9-(2-phenylethyl)-9H-purine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 9-(2-phenylethyl)purine
  参考文献：
  名称：

  TBHP 通过 Minisci 型反应诱导无金属直接酰化嘌呤以获得 C6 酰化嘌呤衍生物

  摘要：

  开发了一种用醛对嘌呤进行无金属 C-H 官能化的方法，以通过绿色自由基反应获得 C 6 -酰化嘌呤。理论上，由于嘌呤中的三个C-H键（C 2 -H、C 6 -H、C 8 -H），存在多种竞争反应，酰化仅发生在嘌呤基C 6位。该方法避免了金属催化剂，提供了一种在嘌呤基C 6位构建C-C (sp 2 )键的绿色方法，同时保持与各种官能团的优异相容性。此外，该协议具有广泛的底物范围和易于放大的特点。产品的转化证明了该方法具有显着的实用价值。主要机制是根据对照实验提出的。

  DOI：

  10.1039/d3nj05712g

文献信息

• 6-(Alkylamino)-9-benzyl-9H-purines. A new class of anticonvulsant agents
  作者：James L. Kelley、Mark P. Krochmal、James A. Linn、Ed W. McLean、Francis E. Soroko

  DOI：10.1021/jm00398a019

  日期：1988.3

  electroshock-induced seizures (MES) in rats. Most compounds were prepared in three steps from 5-amino-4,6-dichloropyrimidine or in two steps via alkylation of 6-chloropurine. Potent anticonvulsant activity against MES resided in compounds that contain a benzyl substituent at the 9-position of 6-(methylamino)- or 6-(dimethyl-amino)purine. Among commonly used agents for control of seizures, this type of structure represents

  合成了几种9-烷基-6-取代的嘌呤，并测试了其对大鼠最大电击诱发的癫痫发作（MES）的抗惊厥活性。大多数化合物是从3-氨基-4,6-二氯嘧啶分三步制备的，也可以通过6-氯嘌呤的烷基化分两步制备的。针对MES的有效的抗惊厥活性存在于在6-（甲基氨基）-或6-（二甲基-氨基）嘌呤的9位上含有苄基取代基的化合物中。在控制癫痫发作的常用药物中，这种类型的结构代表了一类新型的强效惊厥药物。
• Copper-Catalyzed Synthesis of Purine-Fused Polycyclics
  作者：Gui-Rong Qu、Lei Liang、Hong-Ying Niu、Wei-Hao Rao、Hai-Ming Guo、John S. Fossey

  DOI：10.1021/ol301848v

  日期：2012.9.7

  A novel protocol for a Cu-catalyzed direct C-(sp2)-H activation/intramolecular amination reaction of 6-anilinopurine nucleosides has been developed. This approach provides a new access to a variety of multiheterocyclic compounds from purine compounds via Cu-catalyzed intramolecular N-H bond tautomerism which are endowed with fluorescence.
• Highly Regioselective Three-Component Domino Heck–Negishi Coupling Reaction for the Functionalization of Purines at C6
  作者：Dong-Chao Wang、Hong-Ying Niu、Ming-Sheng Xie、Gui-Rong Qu、Hui-Xuan Wang、Hai-Ming Guo

  DOI：10.1021/ol4032683

  日期：2014.1.3

  A highly regioselective three-component domino Heck-Negishi coupling reaction has been developed. Organozinc reagents are used to trap an alkylpalladium intermediate of olefins for a first example in the domino Heck reaction. This reaction is applicable to acrylates (or acrylamides) and purine compounds, producing a series of novel purine compounds with carbon substituents at the C6 position in moderate to good yields.
• Synthesis and Antimycobacterial Activity of 6-Arylpurines:  The Requirements for the <i>N</i>-9 Substituent in Active Antimycobacterial Purines
  作者：Lise-Lotte Gundersen、Jon Nissen-Meyer、Bjørn Spilsberg

  DOI：10.1021/jm0110284

  日期：2002.3.1

  6-Arylpurines carrying a variety of substituents in the 9-position were prepared by Stille coupling between appropriately substituted 6-chloropurines and aryl(tributyl)tin, and the compounds were screened for antibacterial activity against Mycobacterium tuberculosis H-37-Rv. The lowest minimum inhibitory concentration value, 0.78 mug/mL, was found for 9-benzyl-2-chloro-6-(2-furyl)purine. This compound exhibited relatively low cytotoxicity, and it was active against several singly drug-resistant strains of M. tuberculosis.
• KELLEY, JAMES L.;KROCHMAL, MARK P.;LINN, JAMES A.;MCJEAN, ED W.;SOROKO, F+, J. MED. CHEM., 31,(1988) N 3, 606-612
  作者：KELLEY, JAMES L.、KROCHMAL, MARK P.、LINN, JAMES A.、MCJEAN, ED W.、SOROKO, F+

  DOI：——

  日期：——