(1R)-6-chloro-9-(1-phenylethyl)-9H-purine | 112089-30-2

• 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: (1R)-6-chloro-9-(1-phenylethyl)-9H-purine
• 英文别名: (R)-6-chloro-9-(1-phenylethyl)-9H-purine；6-chloro-9-[(1R)-1-phenylethyl]purine
• CAS: 112089-30-2
• 化学式: C₁₃H₁₁ClN₄
• 分子量: 258.71
• InChiKey: XTFDZVGPYVRMGL-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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-(三丁基锡烷基)呋喃 、 (1R)-6-chloro-9-(1-phenylethyl)-9H-purine 在 bis(triphenylphosphine)palladium(II)-chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以94%的产率得到6-(2-furyl)-9-[(1R)-1-phenylethyl]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

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。
• 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：——
• 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.