6-chloro-9-(2,6-difluorophenylmethyl)-9H-purine | 113669-20-8

• 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-(2,6-difluorophenylmethyl)-9H-purine
• 英文别名: 6-chloro-9-(2,6-difluorobenzyl)-9H-purine；6-chloro-9-(2,6-difluorobenzyl)purine；6-Chloro-9-[(2,6-difluorophenyl)methyl]purine
• CAS: 113669-20-8
• 化学式: C₁₂H₇ClF₂N₄
• 分子量: 280.664
• InChiKey: ZEWWKNRERLPOBF-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  432.6±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(2,6-difluorophenylmethyl)-9H-purine 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以88%的产率得到9-(2,6-difluorobenzyl)hypoxanthine
  参考文献：
  名称：

  Synthesis ofN-Aryl Uracils and Hypoxanthines and Their Biological Properties

  摘要：

  1-Benzyluracils 2a,b were treated with iodobenzene in the presence of cuprous oxide in 2,4,6-trimethylpyridine at 180 degrees C to give the N'-phenyl derivatives 3a and 3b in 47% and 55%, respectively. Similar reaction of 2a with 2-bromopyridine at 120 degrees C gave the 3-(2-pyridinyl)uracil 4a in 42% yield. However, unusual product 5 as well as 3-(2-pyridinyl) derivative 4b were obtained in the case of 2b. The structure of 5 was identified as 1-(2,6-difluorobenzyl)-3-[(2,4-dimethyl-2-pyridinyl)methyl]uracil from spectroscopic data Reaction of the hypoxanthines 7a,b with 2-bromopyridine gave the 1-(2-pyridinyl)hypoxanthines 8a,b in low yields. But N-phenylation of 7a,b were unsuccessful.

  DOI：

  10.1080/15257779908041534
• 作为产物：
  描述：

  2,6-二氟溴苄 、 6-氯嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以42%的产率得到6-chloro-9-(2,6-difluorophenylmethyl)-9H-purine
  参考文献：
  名称：

  Synthesis ofN-Aryl Uracils and Hypoxanthines and Their Biological Properties

  摘要：

  1-Benzyluracils 2a,b were treated with iodobenzene in the presence of cuprous oxide in 2,4,6-trimethylpyridine at 180 degrees C to give the N'-phenyl derivatives 3a and 3b in 47% and 55%, respectively. Similar reaction of 2a with 2-bromopyridine at 120 degrees C gave the 3-(2-pyridinyl)uracil 4a in 42% yield. However, unusual product 5 as well as 3-(2-pyridinyl) derivative 4b were obtained in the case of 2b. The structure of 5 was identified as 1-(2,6-difluorobenzyl)-3-[(2,4-dimethyl-2-pyridinyl)methyl]uracil from spectroscopic data Reaction of the hypoxanthines 7a,b with 2-bromopyridine gave the 1-(2-pyridinyl)hypoxanthines 8a,b in low yields. But N-phenylation of 7a,b were unsuccessful.

  DOI：

  10.1080/15257779908041534

文献信息

• 9-(2-Fluorobenzyl)-6-(alkylamino)-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/jm00400a019

  日期：1988.5

  Several substituted aryl and 6-alkylamino analogues of the anticonvulsant purine 9-(2-fluorobenzyl)-6-(methyl-amino)-9H-purine (1) were synthesized and tested for anticonvulsant activity against maximal electroshock-induced seizures (MES) in rats. Derivatives with a second fluoro substituent in the 5- or 6-position of the aryl moiety were very active with ip ED50's that ranged from 2 to 4 mg/kg. Congeners

  合成了抗惊厥嘌呤9-（2-氟苄基）-6-（甲基氨基）-9H-嘌呤（1）的几种取代的芳基和6-烷基氨基类似物，并测试了其对最大电击诱发癫痫发作（MES）的抗惊厥活性。在大鼠中。在芳基部分的5-或6-位具有第二个氟取代基的衍生物具有非常高的活性，ip ED50的范围为2-4 mg / kg。嘌呤6取代基在许多烷基氨基基团中发生变化的同类物对MES的有效活性与苯妥英相当或比苯妥英好几倍。
• Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines
  作者：Anne Kristin Bakkestuen、Lise-Lotte Gundersen、Bibigul T. Utenova

  DOI：10.1021/jm0408924

  日期：2005.4.1

  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.
• Synthesis of<i>N</i>-Aryl Uracils and Hypoxanthines and Their Biological Properties
  作者：Tokumi Maruyama、Shigetada Kozai、Mayuko Uchida

  DOI：10.1080/15257779908041534

  日期：1999.4

  1-Benzyluracils 2a,b were treated with iodobenzene in the presence of cuprous oxide in 2,4,6-trimethylpyridine at 180 degrees C to give the N'-phenyl derivatives 3a and 3b in 47% and 55%, respectively. Similar reaction of 2a with 2-bromopyridine at 120 degrees C gave the 3-(2-pyridinyl)uracil 4a in 42% yield. However, unusual product 5 as well as 3-(2-pyridinyl) derivative 4b were obtained in the case of 2b. The structure of 5 was identified as 1-(2,6-difluorobenzyl)-3-[(2,4-dimethyl-2-pyridinyl)methyl]uracil from spectroscopic data Reaction of the hypoxanthines 7a,b with 2-bromopyridine gave the 1-(2-pyridinyl)hypoxanthines 8a,b in low yields. But N-phenylation of 7a,b were unsuccessful.