N-[(2-甲氧基苯基)甲基]-7H-嘌呤-6-胺 | 75737-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: N-[(2-甲氧基苯基)甲基]-7H-嘌呤-6-胺
• 英文名称: 6-o-methoxybenzylaminopurine
• 英文别名: 6-(2-methoxylbenzylamino)purine；6-(2-methoxybenzylamino)purine；2-MeOBap；N-(2-methoxybenzyl)-9H-purin-6-amine；N-[(2-methoxyphenyl)methyl]-7H-purin-6-amine
• CAS: 75737-41-6
• 化学式: C₁₃H₁₃N₅O
• 分子量: 255.279
• InChiKey: STWJKIOLMNHFIK-UHFFFAOYSA-N

物化性质

• 熔点：
  260-261 °C
• 沸点：
  413.2±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  盐酸 、 potassium hexachloropalatinate(IV) 、 N-[(2-甲氧基苯基)甲基]-7H-嘌呤-6-胺 以 盐酸 为溶剂， 生成 [Pt(6-(2-methoxybenzylamino)purine(+H))Cl5]
  参考文献：
  名称：

  The first platinum(IV) complexes involving aromatic cytokinins or cyclin-dependent kinase inhibitors derived from 6-benzylaminopurine: X-ray structures of (BohH22+)[PtCl6]·H2Oand(RosH22+)2[PtCl6]Cl2·4H2O

  摘要：

  A series of Pt(IV) complexes with cytokinins or CDK-inhibitors derived from 6-benzylaminopurine (Bap) of the composition [Pt-IV(LH+)Cl-5] (1-14), where LH+ stands for protonated form of the Bap derivative (1-12), Boh = 6-(benzylamino)-2-[(3-hydroxypropyl)amino]-9-isopropylpurine, bohemine (13) and Ros = 6-(benzylamino)-2-[(1-hydroxymethylpropyl)amino]-9-isopropylpurine, roscovitine (14), have been prepared. They have been fully characterized by microanalysis, conductivity, FT-IR, H-1, C-13, N-15 and Pt-195 NMR and ES+ mass spectroscopy. It has been found that the cytokinin molecule is coordinated via N9 atom to platinum(IV) and N1, N7-protonated in case of complexes 1-12, and N7 coordinated and NI-protonated in case of complexes with CDK inhibitors (13 and 14). Predicted molecular geometries of the complexes have been supported by DFT calculations at the B3LYP level with the 6-311+G**/LANL2DZ and aug-cc-pVDZ/LANL2DZ basis sets. All of the compounds have been tested in vitro for their cytotoxicity against four human cancer cell lines: malignant melanoma (G361), osteogenic sarcoma (HOS), chronic myelogenous erythroleukemia (K562) and breast adenocarcinoma (MCF7). The best result has been achieved for complex 14, where IC50 = 17 mu M against K562. The molecular structures of two ionic pair compounds (BohH(2)(2+))[PtCl6] center dot H2O (15) and (RosH(2)(2+))(2)[PtCl6]Cl-2 center dot 4H(2)O (16) have been determined by a single crystal X-ray analysis. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2007.07.026
• 作为产物：
  描述：

  邻甲氧基苄胺 、 6-氯嘌呤 以 正丁醇 为溶剂， 生成 N-[(2-甲氧基苯基)甲基]-7H-嘌呤-6-胺
  参考文献：
  名称：

  细胞分裂素活性腺嘌呤和尿素衍生物的定量构效关系

  摘要：

  摘要 采用理化取代基参数和回归分析，定量分析了N 6 -烷基和-芳烷基腺嘌呤对烟草愈伤组织生长的促进作用。结果表明，就N 6 取代基距连接N 6 原子与其α碳原子的键轴的最大宽度而言，活性的最佳空间条件。N 6 取代基的吸电子作用增强了活性。还分析了 Bruce 和 Zwar 使用烟草髓块测定法测定的取代基对苯基和二苯基脲衍生物的细胞分裂素活性的影响。结果表明，芳香族取代基的位置特异性空间和疏水作用参与了活性的变化，使活性的总体趋势合理化；元 > 对 > 邻位衍生物，用于两个系列的化合物。电子效应对二苯脲的活性很重要，但对苯脲的活性不重要，苯脲在作用位点的两个系列之间的相互作用模式略有不同。根据相关性的推论，已经提出了这三组化合物在作用部位的相互作用模式的假设图。

  DOI：

  10.1016/0031-9422(80)80165-8

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。
• [EN] COMPOUNDS FOR IMPROVING MRNA SPLICING<br/>[FR] COMPOSÉS POUR AMÉLIORER L'ÉPISSAGE DE L'ARNM
  申请人：GEN HOSPITAL CORP

  公开号：WO2016115434A1

  公开（公告）日：2016-07-21

  Provided herein are compounds useful for improving mRNA splicing in a cell. Exemplary compounds provided herein are useful for improving mRNA splicing in genes comprising at least one exon ending in the nucleotide sequence CAA. Methods for preparing the compounds and methods of treating diseases of the central nervous system are also provided.

  本文提供了一些有助于改善细胞内mRNA剪接的化合物。本文提供的示例化合物有助于改善包含至少一个以核苷酸序列CAA结尾的外显子的基因的mRNA剪接。还提供了制备这些化合物的方法以及治疗中枢神经系统疾病的方法。
• [EN] COMPOSITIONS AND METHODS OF USING THE SAME FOR TREATMENT OF NEURODEGENERATIVE AND MITOCHONDRIAL DISEASE<br/>[FR] COMPOSITIONS ET LEURS MÉTHODE D'UTILISATION POUR LE TRAITEMENT D'UNE MALADIE NEURODEGENERATIVE ET MITOCHONDRIALE
  申请人：MITOKININ INC

  公开号：WO2020206363A1

  公开（公告）日：2020-10-08

  The present disclosure is directed to nitrogen-containing heteroaryl analogs, methods of making nitrogen-containing analogs, and methods of treating disorders associated with PINK1 kinase activity including, but not limited to, neurodegenerative diseases, mitochondrial diseases, fibrosis, and/or cardiomyopathy using these analogs. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本公开涉及含氮杂环类似物，制备含氮类似物的方法，以及使用这些类似物治疗与PINK1激酶活性相关的疾病的方法，包括但不限于神经退行性疾病、线粒体疾病、纤维化和/或心肌病。本摘要旨在作为在特定领域进行搜索的扫描工具，并不打算限制本发明。
• [EN] CYCLOBUTAN-1,1 -DICARBOXYLATO COMPLEXES OF PLATINUM WITH N6-BENZYLADENINE DERIVATIVES, METHOD OF THEIR PREPARATION AND APPLICATION OF THESE COMPLEXES AS DRUGS IN ANTITUMOUR THERAPY<br/>[FR] COMPLEXES CYCLOBUTANE-1,1-DICARBOXYLATO DE PLATINE AVEC DES DÉRIVÉS DE N6-BENZYLADÉNINE, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR APPLICATION EN TANT QUE MÉDICAMENTS DANS UN TRAITEMENT ANTITUMORAL
  申请人：UNIV PALACKEHO

  公开号：WO2011029415A1

  公开（公告）日：2011-03-17

  Cyclobutane-1,1-dicarboxylato complexes of platinum in the oxidation state +II and their crystal-solvates including the structural motif I or having the general formula Il expressed by the structural formula [Pt(cbdc)(L)2] Il or the general formula III expressed by the structural formula [Pt(cbdc)(L)(L')] III, where the symbols L and L' stand for N6-benzyladenine derivatives of the general formula IV bound to the platinum atom of the basic motif V through any adenine nitrogen atom independently chosen from the N1, N3, N6, N7 or N9 atoms, depending on the substitution rate of the molecules IV, where the substituents R1, R2 a R3 are independently chosen from the group of: hydrogen atom, halogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, cycloalkenyl, substituted cycloalkenyl, cycloheteroalkenyl, substituted cycloheteroalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, functional group and N-R'R" group, where R' and R" independently symbolize hydrogen atom, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, cycloalkenyl, substituted cycloalkenyl, cycloheteroalkenyl, substituted cycloheteroalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl and functional group.

  铂的氧化态为+II的环丁二酸-1,1-二羧酸配合物及其晶体溶剂包括结构基团I或具有由结构式[Pt(cbdc)(L)2] II表示的一般式Il或由结构式[Pt(cbdc)(L)(L')] III表示的一般式III，其中符号L和L'代表通式IV的N6-苄腺嘌呤衍生物，通过任何腺嘌呤氮原子独立选择自N1、N3、N6、N7或N9原子与基本基团V的铂原子结合，取决于分子IV的取代率，其中取代基R1、R2和R3独立选择自以下组中的: 氢原子、卤素、烷基、取代烷基、烯基、取代烯基、炔基、取代炔基、环烷基、取代环烷基、环杂烷基、取代环杂烷基、环烯基、取代环烯基、环杂烯基、取代环杂烯基、芳基、取代芳基、杂芳基、取代杂芳基、功能基团和N-R'R"基团，其中R'和R"独立表示氢原子、烷基、取代烷基、烯基、取代烯基、炔基、取代炔基、环烷基、取代环烷基、环杂烷基、取代环杂烷基、环烯基、取代环烯基、环杂烯基、取代环杂烯基、芳基、取代芳基、杂芳基、取代杂芳基和功能基团。
• 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。