2,6-dichloro-9-(4-methylphenylmethyl)-9H-purine | 115204-73-4

• 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: 2,6-dichloro-9-(4-methylphenylmethyl)-9H-purine
• 英文别名: 2,6-dichloro-9-(4-methylbenzyl)-9H-purine；2,6-Dichloro-9-[(4-methylphenyl)methyl]purine
• CAS: 115204-73-4
• 化学式: C₁₃H₁₀Cl₂N₄
• 分子量: 293.155
• InChiKey: WLKCCQUQUMTKLX-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C
• 沸点：
  441.9±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 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：

  2,6-dichloro-9-(4-methylphenylmethyl)-9H-purine 、 2-(三丁基锡烷基)呋喃 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74%的产率得到2-chloro-6-(2-furyl)-9-(4-methylphenylmethyl)-9H-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：

  对二甲苯 、 2,6-二氯嘌呤 在 叔丁基过氧化氢 、 四丁基碘化铵 作用下， 以 水 为溶剂， 反应 12.0h， 以80%的产率得到2,6-dichloro-9-(4-methylphenylmethyl)-9H-purine
  参考文献：
  名称：

  Metal-free, highly efficient organocatalytic amination of benzylic C–H bonds

  摘要：

  在无金属条件下,已开发出一种通过sp3 C-H活化实现直接C-N键形成的新型合成方法。初级和次级苄基C-H底物都能与各种胺类发生反应,只生成单胺化产物,产率从良好到优秀。

  DOI：

  10.1039/c3cc41558a

文献信息

• Purine compounds
  申请人：Gundersen Lise-Lotte

  公开号：US20070203159A1

  公开（公告）日：2007-08-30

  The invention provides an antimycobacterial 6-aryl-9-(m- or p-substituted-benzyl) purine and purine analog compounds.

  这项发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。
• Synthesis of 8-Bromo-<i>N</i>-benzylpurines via 8-Lithiated Purines: Scope and Limitations
  作者：Thywill Gamadeku、Lise-Lotte Gundersen

  DOI：10.1080/00397910903318708

  日期：2010.8.16

  9-Benzylpurines have been lithiated in the 8-position and subsequently brominated when trapped with BrCCl2CCl2Br. The 8-bromopurines were isolated in excellent yields when the benzyl group carried an alkoxy or alkyl group in the ortho or para position. Without these substituents, the conversion was generally less, and formation of 8,8'-purinyl dimers was observed. There was also evidence of debenzylation in some instances. Bromination of 7-benzylpurines employing the same set of reaction conditions has also been achieved.
• Antirhinovirus activity of 6-anilino-9-benzyl-2-chloro-9H-purines
  作者：James L. Kelley、James A. Linn、J. W. T. Selway

  DOI：10.1021/jm00167a012

  日期：1990.5

  A series of 6-anilino-9-benzyl-2-chloropurines was synthesized and tested for antirhinovirus activity. Most of the compounds were prepared by reaction of the appropriate aniline with 9-benzyl-2,6-dichloro-9H-purine. Structure-activity relationship studies revealed that compounds with small, lipophilic para substituents were good inhibitors of serotype 1B. Several compounds had good activity against four representative serotypes.
• 9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity
  作者：James L. Kelley、James A. Linn、Mark P. Krochmal、J. W. T. Selway

  DOI：10.1021/jm00118a025

  日期：1988.10

  A series of 9-benzyl-6-(dimethylamino)-9H-purines and 9-benzyl-2-chloro-6-(dimethylamino)-9H-purines were synthesized and tested in cell culture for activity against rhinovirus type 1B. The 9-benzylpurines that were unsubstituted in the 2-position had weak activity. However, introduction of a 2-chloro substituent resulted in a substantial increase in antiviral activity. One of the most active compounds, 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine (29), had an IC50 value of 0.08 microM against serotype 1B. Four compounds were tested against 18 other rhinovirus serotypes, but the majority tested were less sensitive than type 1B. The range of serotype sensitivity for 29 varied from 0.08 to 14 microM. These 9-benzyl-2-chloro-9H-purines represent a new class of antiviral agents with in vitro activity against rhinoviruses.
• KELLEY, JAMES L.;LINN, JAMES A.;KROCHMAL, MARK P.;SELWAY, J. W. T., J. MED. CHEM., 31,(1988) N 10, C. 2001-2004
  作者：KELLEY, JAMES L.、LINN, JAMES A.、KROCHMAL, MARK P.、SELWAY, J. W. T.

  DOI：——

  日期：——