2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine | 115204-55-2

• 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: 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine
• 英文别名: 2-chloro-N,N-dimethyl-9-(p-tolylmethyl)purin-6-amine；2-chloro-N,N-dimethyl-9-[(4-methylphenyl)methyl]purin-6-amine
• CAS: 115204-55-2
• 化学式: C₁₅H₁₆ClN₅
• 分子量: 301.779
• InChiKey: XESMUWWPNVDSKD-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C(Solv: hexane (110-54-3); toluene (108-88-3))
• 沸点：
  461.4±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine 、 甲胺 以 乙醇 、 水 为溶剂， 以56%的产率得到6-(dimethylamino)-2-(methylamino)-9-(4-methylbenzyl)-9H-purine
  参考文献：
  名称：

  具有抗鼻病毒活性的2-取代-6-（二甲基氨基）-9-（4-甲基苄基）-9H-嘌呤的合成与构效关系。

  摘要：

  一系列2-取代的6-（二甲氨基）-9-（4-甲基苄基）-9H-嘌呤，其中2个取代基是H，F，Cl，CF3，CH3，CH2CH3，NH2，NHCH3，N（CH3）如图2所示，合成SCH3或SO2CH3并测试其抗鼻病毒的活性，以评估2-取代基对抗病毒活性的影响。直观和定量的结构-活性关系（QSAR）分析表明，最佳的鼻病毒性血清型1B活性与包含C-2亲脂性，吸电子取代基的9-苄基嘌呤有关。活性最高的化合物6-（二甲基氨基）-9-（4-甲基苄基）-2-（三氟甲基）-9H-嘌呤（14）对1B型血清型的IC50 = 0.03 microM，但对18种其他血清型的活性为不均匀 IC50的范围超过260倍。

  DOI：

  10.1021/jm00121a039
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 40.0h， 生成 2-chloro-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purine
  参考文献：
  名称：

  9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity

  摘要：

  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.

  DOI：

  10.1021/jm00118a025

文献信息

• 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：——
• 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.
• Synthesis and structure-activity relationships of 2-substituted-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purines with antirhinovirus activity
  作者：James L. Kelley、James A. Linn、J. W. T. Selway

  DOI：10.1021/jm00121a039

  日期：1989.1

  2-substituted-6-(dimethylamino)-9-(4-methylbenzyl)-9H-purines where the 2-substituent was H, F, Cl, CF3, CH3, CH2CH3, NH2, NHCH3, N(CH3)2, SCH3, or SO2CH3 was synthesized and tested for antirhinovirus activity to evaluate the effect of 2-substituents on antiviral activity. Intuitive and quantitative structure-activity relationship (QSAR) analysis showed that optimum antirhinovirus serotype 1B activity was associated

  一系列2-取代的6-（二甲氨基）-9-（4-甲基苄基）-9H-嘌呤，其中2个取代基是H，F，Cl，CF3，CH3，CH2CH3，NH2，NHCH3，N（CH3）如图2所示，合成SCH3或SO2CH3并测试其抗鼻病毒的活性，以评估2-取代基对抗病毒活性的影响。直观和定量的结构-活性关系（QSAR）分析表明，最佳的鼻病毒性血清型1B活性与包含C-2亲脂性，吸电子取代基的9-苄基嘌呤有关。活性最高的化合物6-（二甲基氨基）-9-（4-甲基苄基）-2-（三氟甲基）-9H-嘌呤（14）对1B型血清型的IC50 = 0.03 microM，但对18种其他血清型的活性为不均匀 IC50的范围超过260倍。