2,6-dichloro-9-(4-nitrobenzyl)-9H-purine | 115204-75-6

• 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-nitrobenzyl)-9H-purine
• 英文别名: 2,6-Dichloro-9-[(4-nitrophenyl)methyl]purine
• CAS: 115204-75-6
• 化学式: C₁₂H₇Cl₂N₅O₂
• 分子量: 324.126
• InChiKey: GIDMROBNQFGZCC-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C(Solvent: Ethanol)
• 沸点：
  521.5±60.0 °C(predicted)
• 密度：
  1.71±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-9-(4-nitrobenzyl)-9H-purine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 18.5h， 生成 9-[(4-氨基苯基)甲基]-2-氯-N,N-二甲基嘌呤-6-胺
  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
• 作为产物：
  描述：

  2,6-二氯嘌呤 、 对硝基溴化苄 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 22.0h， 以27%的产率得到2,6-dichloro-9-(4-nitrobenzyl)-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

• [EN] 2-MORPHOLINYLPURINES AS INHIBITORS OF PI3K<br/>[FR] 2 -MORPHOLINYLPURINES EN TANT QU'INHIBITEURS DE PI3K
  申请人：S BIO PTE LTD

  公开号：WO2009045174A1

  公开（公告）日：2009-04-09

  The present invention relates to purine compounds 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 disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases.

  本发明涉及作为激酶抑制剂有用的嘌呤化合物。更具体地说，本发明涉及嘌呤化合物、其制备方法、含有这些化合物的药物组合物以及在治疗增殖性疾病中使用这些化合物的用途。这些化合物可能作为药物用于治疗多种增殖性疾病，包括肿瘤和癌症以及与mTOR激酶相关的其他疾病或症状。
• 2-MORPHOLINYLPURINES AS INHIBITORS OF PI3K
  申请人：Nagaraj Harish Kumar Mysore

  公开号：US20110009403A1

  公开（公告）日：2011-01-13

  The present invention relates to purine compounds 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 disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases.

  本发明涉及嘌呤化合物，可用作激酶抑制剂。更具体地说，本发明涉及嘌呤化合物、其制备方法、含有这些化合物的药物组合物以及这些化合物在治疗增殖性疾病方面的用途。这些化合物可以作为药物治疗多种增殖性疾病，包括肿瘤和癌症以及与mTOR激酶相关或相关的其他疾病或病况。
• 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.