(2-aminobenzyl)-(2-chloro-9-isopropyl-9H-purin-6-yl)-amine | 1236968-93-6

• 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-aminobenzyl)-(2-chloro-9-isopropyl-9H-purin-6-yl)-amine
• 英文别名: 6-[(2-aminobenzyl)amino]-2-chloro-9-isopropylpurine；N-[(2-aminophenyl)methyl]-2-chloro-9-propan-2-ylpurin-6-amine
• CAS: 1236968-93-6
• 化学式: C₁₅H₁₇ClN₆
• 分子量: 316.793
• InChiKey: HLPYJNIZVCLWEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基-2-甲基-2-丁醇 、 (2-aminobenzyl)-(2-chloro-9-isopropyl-9H-purin-6-yl)-amine 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 72.0h， 以27%的产率得到4-({6-[(2-aminobenzyl)amino]-9-isopropyl-9H-purin-2-yl}amino)-2-methyl-butan-2-ol
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of 2,6,9-trisubstituted purines targeting multiple cyclin-dependent kinases

  摘要：

  Several inhibitors of cyclin-dependent kinases (CDKs), including the 2,6,9-trisubstituted purine derivative roscovitine, are currently being evaluated in clinical trials as potential anticancer drugs. Here, we describe a new series of roscovitine derivatives that show increased potency in vitro. The series was tested for cytotoxicity against six cancer cell lines and for inhibition of CDKs. For series bearing 2-(hydroxyalkylamino) moiety, cytotoxic potency strongly correlated with anti-CDK2 activity. Importantly, structural changes that increase biochemical and anticancer activities of these compounds also increase elimination half-life. The most potent compounds were investigated further to assess their ability to influence cell cycle progression, p53-regulated transcription and apoptosis. All the observed biological effects were consistent with inhibition of CDKs involved in the regulation of cell cycle and transcription. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.036
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 偶氮二甲酸二异丙酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 丙醇 为溶剂， 反应 6.0h， 生成 (2-aminobenzyl)-(2-chloro-9-isopropyl-9H-purin-6-yl)-amine
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of 2,6,9-trisubstituted purines targeting multiple cyclin-dependent kinases

  摘要：

  Several inhibitors of cyclin-dependent kinases (CDKs), including the 2,6,9-trisubstituted purine derivative roscovitine, are currently being evaluated in clinical trials as potential anticancer drugs. Here, we describe a new series of roscovitine derivatives that show increased potency in vitro. The series was tested for cytotoxicity against six cancer cell lines and for inhibition of CDKs. For series bearing 2-(hydroxyalkylamino) moiety, cytotoxic potency strongly correlated with anti-CDK2 activity. Importantly, structural changes that increase biochemical and anticancer activities of these compounds also increase elimination half-life. The most potent compounds were investigated further to assess their ability to influence cell cycle progression, p53-regulated transcription and apoptosis. All the observed biological effects were consistent with inhibition of CDKs involved in the regulation of cell cycle and transcription. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.036

文献信息

• SUBSTITUTED 6-(2-AMINOBENZYLAMINO)PURINE DERIVATIVES, THEIR USE AS MEDICAMENTS AND PREPARATIONS CONTAINING THESE COMPOUNDS
  申请人：Havlicek Libor

  公开号：US20110287111A1

  公开（公告）日：2011-11-24

  The invention relates to new substituted 6-(2-aminobenzylamino)purines, represented by the general formula I, which can be used in CDK inhibition, in particular, in the treatment of viral infections and diseases involving cell proliferation. The invention further includes pharmaceutical preparations containing substituted 6-(2-aminobenzylamino)purines.

  本发明涉及一种新型的取代6-(2-氨基苯基氨基)嘌呤，其通式为I，可用于CDK抑制，特别是用于治疗病毒感染和涉及细胞增殖的疾病。本发明还包括含有取代的6-(2-氨基苯基氨基)嘌呤的药物制剂。
• [EN] SUBSTITUTED 6-(2-AMINOBENZYLAMINO)PURINE DERIVATIVES, THEIR USE AS MEDICAMENTS AND PREPARATIONS CONTAINING THESE COMPOUNDS<br/>[FR] DÉRIVÉS DE 6-(2-AMINOBENZYLAMINO)PURINE SUBSTITUÉE, UTILISATION DE CEUX-CI EN TANT QUE MÉDICAMENTS, ET PRÉPARATIONS CONTENANT CES COMPOSÉS
  申请人：UNIVERZITA PALACKEHO V OLOMOUC

  公开号：WO2010085924A3

  公开（公告）日：2010-09-30
• US9023857B2
  申请人：——

  公开号：US9023857B2

  公开（公告）日：2015-05-05