2,6-dichloro-9-p-tolyl-9H-purine | 395087-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,6-dichloro-9-p-tolyl-9H-purine
• 英文别名: 2,6-dichloro-9-(4-methylphenyl)-purine；2,6-dichloro-9-(4-methylphenyl)purine
• CAS: 395087-84-0
• 化学式: C₁₂H₈Cl₂N₄
• 分子量: 279.128
• InChiKey: DAKZGEGGEKAXMS-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  376.5±52.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2,6-二氯嘌呤	2,6 dichloropurine	5451-40-1	C5H2Cl2N4	189.004

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2-Chloro-6-(2-furyl)-9-(p-tolyl)purine	——	C16H11ClN4O	310.743

反应信息

• 作为反应物：
  描述：

  2-(三丁基锡烷基)呋喃 、 2,6-dichloro-9-p-tolyl-9H-purine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(2-呋喃基)膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以56%的产率得到2-Chloro-6-(2-furyl)-9-(p-tolyl)purine
  参考文献：
  名称：

  Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

  摘要：

  9-Aryl-, 9-arylsulfonyl- and 9-benzyl-6-(2-furyl)purines were synthesized by N-alkylation or N-arylation of the purine followed by Stille coupling to introduce the faryl substituent in the 6-position and the compounds screened for activity against Mycobacterium tuberculosis. The 9-aryl- and 9-sulfonylarylpurines exhibited weak activity toward the bacteria, but 9-benzylpurines were good inhibitors especially those carrying electron-donating substituents on the phenyl ring. A chlorine atom in the purine 2-position further enhanced activity. The high antimycobacterial activity (MIC 0.39,mu g/mL against M. tuberculosis), low toxicity against mammalian cells and activity inside macrophages found for 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)9H-purine makes this compound a highly interesting potential antituberculosis drug.

  DOI：

  10.1021/jm0408924
• 作为产物：
  描述：

  4-碘甲苯 在 硫酸 、 potassium carbonate 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 2,6-dichloro-9-p-tolyl-9H-purine
  参考文献：
  名称：

  CuBr催化嘌呤和二芳基碘鎓盐与9-芳基嘌呤的C–N交叉偶联反应†

  摘要：

  CuBr被发现是嘌呤盐和二芳基碘鎓盐的C–N交叉偶联反应的有效催化剂。9-芳基嘌呤以极短的反应时间（2.5h）以优异的产率合成。该方法是通过以芳基硼酸为芳基化剂的Cu（II）催化的C–N偶联反应合成9-芳基嘌呤的替代方法。

  DOI：

  10.1039/c1ob05333g

文献信息

• Kinase inhibitor scaffolds and methods for their preparation
  申请人：IRM LLC, a Delaware Limited Liability Company

  公开号：US20030191312A1

  公开（公告）日：2003-10-09

  General methods for the solution phase as well as solid phase synthesis of various substituted heteroaryls has been demonstrated. These substituted heteroaryls can be further elaborated by aromatic substitution with amines at elevated temperature or by anilines, boronic acids and phenols via palladium catalyzed cross-coupling reactions.

  已经展示了解决各种取代杂环烷基的溶液相和固相合成的一般方法。这些取代杂环烷基可以通过在高温下与胺发生芳香取代，或者通过钯催化的交叉偶联反应与苯胺、硼酸和酚进一步扩展。
• Expanding the diversity of purine libraries
  作者：Sheng Ding、Nathanael S Gray、Qiang Ding、Peter G Schultz

  DOI：10.1016/s0040-4039(01)01925-6

  日期：2001.12

  interest in the synthesis of purine derivatives due to the discovery of purine-derived ligands for a variety of nucleotide dependent enzymes. The majority of chemistry has focused on substitution of the purine core structure by alkylation at N9 and nucleophilic–aromatic substitution reactions at C2 and C6. Here we report the syntheses of aryl, N-aryl, O-aryl substituted purine libraries by the palladium-mediated

  近年来，由于发现了嘌呤衍生的用于多种核苷酸依赖性酶的配体，因此在嘌呤衍生物的合成中引起了人们的兴趣。大多数化学方法都集中在通过N9处的烷基化以及C2和C6处的亲核-芳族取代反应来取代嘌呤核心结构。这里，我们报告的芳基，的合成Ñ -芳基，ø -芳基取代的嘌呤库通过在C2位硼酸，苯胺或苯酚的钯介导的偶联，和铜（II）介导的Ñ -arylation与硼酸N9位置。此处描述的化学物质极大地扩展了我们引入不同功能并创建新嘌呤支架的能力。
• [EN] PYRAZINE SUBSTITUTED PURINES<br/>[FR] PURINES SUBSTITUÉES PAR LA PYRAZINE
  申请人：S BIO PTE LTD

  公开号：WO2009157880A1

  公开（公告）日：2009-12-30

  The present invention relates to purine compounds of formula (I) that are useful as kinase inhibitors. More particularly, the present invention relates to purine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative conditions or disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative conditions or disorders including tumours and cancers as well as other disorders or conditions related to or associated with PI3K and/or mTOR kinases.

  本发明涉及式（I）的嘌呤化合物，其作为激酶抑制剂具有用途。更具体地，本发明涉及嘌呤化合物、其制备方法、含有这些化合物的制药组合物以及这些化合物在治疗增殖性疾病或紊乱方面的用途。这些化合物可以作为药物用于治疗许多增殖性疾病或紊乱，包括肿瘤和癌症以及与PI3K和/或mTOR激酶相关或相关的其他紊乱或疾病。
• KINASE INHIBITOR SCAFFOLDS AND METHODS FOR THEIR PREPARATION
  申请人：Ding Sheng

  公开号：US20070191380A1

  公开（公告）日：2007-08-16

  General methods for the solution phase as well as solid phase synthesis of various substituted heteroaryls has been demonstrated. These substituted heteroaryls can be further elaborated by aromatic substitution with amines at elevated temperature or by anilines, boronic acids and phenols via palladium catalyzed cross-coupling reactions.

  展示了各种取代杂环芳基化合物的溶液相和固相合成的一般方法。这些取代杂环芳基化合物可以通过在高温下与胺进行芳香取代，或通过钯催化的交叉偶联反应与苯胺、硼酸和酚进一步精细化合成。
• Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen

  DOI：10.1016/s0040-4039(03)00576-8

  日期：2003.4

  9-Arylpurines are efficiently formed with complete regioselectivity when purines are treated with arylboronic acids in the presence of copper(II) acetate. A variety of substituents on both coupling partners are well tolerated. (C) 2003 Elsevier Science Ltd. All rights reserved.