6-(3,4,5-trimethoxybenzylamino)purine

• 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: 6-(3,4,5-trimethoxybenzylamino)purine
• 英文别名: N-[(3,4,5-trimethoxyphenyl)methyl]-7H-purin-6-amine
• 化学式: C₁₅H₁₇N₅O₃
• 分子量: 315.332
• InChiKey: JNDQVHZQBMFTTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄胺 、 6-氯嘌呤 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 生成 6-(3,4,5-trimethoxybenzylamino)purine
  参考文献：
  名称：

  Preparation and biological activity of 6-benzylaminopurine derivatives in plants and human cancer cells

  摘要：

  To study the structure-activity relationships of aromatic cytokinins, the cytokinin activity at both the receptor and cellular levels, as well as CDK inhibitory and anticancer properties of 38 6-benzylaminopurine (BAP) derivatives were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine with corresponding substituted benzylamines. The majority of synthesised derivatives exhibited high activity in all three of the cytokinin bioassays employed (tobacco callus, wheat senescence and Amaranthus bioassay). The highest activities were obtained in the senescence bioassay. For some compounds tested, significant differences of activity were found in the bioassays used, indicating that diverse recognition systems may operate and suggesting that it may be possible to modulate particular cytokinin-dependent processes with specific compounds. Position-specific steric and hydrophobic effects of different phenyl ring substituents on the variation of biological activity were confirmed. In contrast to their high activity in bioassays, the BAP derivatives were recognised with much lower sensitivity than trans-zeatin in both Arabidopsis thaliana AHK3 and AHK4 receptor assays. The compounds were also investigated for their effects on cyclin-dependent kinase 2 (CDK2) and for antiproliferative properties on cancer and normal cell lines. Several of the tested compounds showed stronger inhibitory activity and cytotoxicity than BAP. There was also a significant positive correlation of the inhibitory effects on human and plant CDKs with cell proliferation of cancer and cytokinin-dependent tobacco cells, respectively. This suggests that at least a part of the antiproliferative effect of the new cytokinins was due to the inhibition of CDK activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.004

文献信息

• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• Heterocyclic compound based on n6-substituted adenine, methods, of their preparation, their use for preparation of drugs, cosmetic preparations and growth regulators, pharmaceutical preparations, cosmetic preparations and growth regulators containing these compounds
  申请人：Dolezal Karel

  公开号：US20050043328A1

  公开（公告）日：2005-02-24

  New heterocyclic derivatives based on N 6 -substituted adenine, having anticancer, mitotic, imunosuppressive and antisenescent propoerties for plant, animal and human cells and methods of their preparation. Included are also pharmaceutical compositions, cosmetic preparations and growth regulators, which contain these derivatives as active compound and the use of these derivatives for the preparation of drugs, cosmetic preparations, in biotechnological processes, in cosmetics and in agriculture.

  基于N6-取代腺嘌呤的新杂环衍生物具有抗癌、有丝分裂、免疫抑制和抗衰老的性质，适用于植物、动物和人类细胞，并提供其制备方法。还包括含有这些衍生物作为活性化合物的药物组合物、化妆品制剂和生长调节剂，以及这些衍生物用于制备药物、化妆品制剂、生物技术过程、化妆品和农业的用途。
• HETEROCYCLIC COMPOUNDS BASED ON N6-SUBSTITUTED ADENINE, METHODS OF THEIR PREPARATION, THEIR USE FOR PREPARATION OF DRUGS, COSMETIC PREPARATIONS AND GROWTH REGULATORS, PHARMACEUTICAL PREPARATIONS, COSMETIC PREPARATIONS AND GROWTH REGULATORS CONTAINING THESE COMPOUNDS
  申请人：Popa Igor

  公开号：US20080014227A1

  公开（公告）日：2008-01-17

  Novel heterocyclic derivatives based on N 6 -substituted adenine, having anticancer, mitotic, immunosuppressive and antisenescent properties for plant, animal and human cells and methods of their preparation. Included are also pharmaceutical compositions, cosmetic preparations and growth regulators, which contain these derivatives as active compound and the use of these derivatives for the preparation of drugs, cosmetic preparations, in biotechnological processes, in cosmetics and in agriculture.

  基于N6-取代腺嘌呤的新型杂环衍生物，具有抗癌、有丝分裂、免疫抑制和抗衰老的性质，适用于植物、动物和人类细胞，以及它们的制备方法。还包括含有这些衍生物作为活性化合物的制药组合物、化妆品制剂和生长调节剂，以及使用这些衍生物制备药物、化妆品制剂、生物技术过程、化妆品和农业的方法。
• HETEROCYCLIC COMPOUND BASED ON N sp 6 /sp −SUBSTITUTED ADENINE, METHODS OF THEIR PREPARATION, THEIR USE FOR PREPARATION OF DRUGS, COSMETIC PREPARATIONS AND GROWTH REGULATORS, PHARMACEUTICAL PREPARATIONS, COSMETIC PREPARATIONS AND GROWTH REGULATORS CONTAINING THESE
  申请人：Ustav Experimentalni Botaniky Akademie ved Ceské Republiky

  公开号：EP1419157A2

  公开（公告）日：2004-05-19
• US7279482B2
  申请人：——

  公开号：US7279482B2

  公开（公告）日：2007-10-09