(2-aminobenzyl)(2-chloro-9-cyclopentyl-9H-purin-6-yl)amine | 1236968-96-9

• 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-cyclopentyl-9H-purin-6-yl)amine
• 英文别名: 6-[(2-aminobenzyl)amino]-2-chloro-9-cyclopentylpurine；N-[(2-aminophenyl)methyl]-2-chloro-9-cyclopentylpurin-6-amine
• CAS: 1236968-96-9
• 化学式: C₁₇H₁₉ClN₆
• 分子量: 342.831
• InChiKey: DOKXZDKVBNKNBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 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-cyclopentyl-9H-purin-6-yl)amine
  参考文献：
  名称：

  A Novel Series of Highly Potent 2,6,9-Trisubstituted Purine Cyclin-Dependent Kinase Inhibitors

  摘要：

  The inhibition of overactive CDKs during cancer remains an important strategy in cancer drug development. We synthesized and screened a novel series of 2-substituted-6-biarylmethylamino-9-cyclopentylpurine derivatives for improved CDK inhibitory activity and antiproliferative effects. One of the most potent compounds, 6b, exhibited strong cytotoxicity in the human melanoma cell line G361 that correlated with robust CDK1 and CDK2 inhibition and caspase activation. In silico modeling of 6b in the active site of CDK2 revealed a high interaction energy, which we believe is due to the 6-heterobiarylmethylamino substitution of the purine moiety.

  DOI：

  10.1021/jm4006884

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。
• US9023857B2
  申请人：——

  公开号：US9023857B2

  公开（公告）日：2015-05-05
• [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：WO2010085924A2

  公开（公告）日：2010-08-05

  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.˙
• A Novel Series of Highly Potent 2,6,9-Trisubstituted Purine Cyclin-Dependent Kinase Inhibitors
  作者：Tomáš Gucký、Radek Jorda、Marek Zatloukal、Václav Bazgier、Karel Berka、Eva Řezníčková、Tibor Béres、Miroslav Strnad、Vladimír Kryštof

  DOI：10.1021/jm4006884

  日期：2013.8.8

  The inhibition of overactive CDKs during cancer remains an important strategy in cancer drug development. We synthesized and screened a novel series of 2-substituted-6-biarylmethylamino-9-cyclopentylpurine derivatives for improved CDK inhibitory activity and antiproliferative effects. One of the most potent compounds, 6b, exhibited strong cytotoxicity in the human melanoma cell line G361 that correlated with robust CDK1 and CDK2 inhibition and caspase activation. In silico modeling of 6b in the active site of CDK2 revealed a high interaction energy, which we believe is due to the 6-heterobiarylmethylamino substitution of the purine moiety.