6-(2-fluorobenzylamino)purine | 67023-50-1

• 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-(2-fluorobenzylamino)purine
• 英文别名: 6-(2-fluorobenzylamino)pyrine；N6-(2-fluorobenzyl)adenine；2-FBap；Adenine,6N-O-fluorobenzyl；N-[(2-fluorophenyl)methyl]-7H-purin-6-amine
• CAS: 67023-50-1
• 化学式: C₁₂H₁₀FN₅
• mdl: MFCD11119602
• 分子量: 243.243
• InChiKey: ZDOQFEFKZILKMM-UHFFFAOYSA-N

物化性质

• 沸点：
  527.3±40.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(2-fluorobenzylamino)purine 、 gold(III) chloride 以 丙酮 为溶剂， 反应 4.0h， 以70%的产率得到[Au(N6-(2-fluorobenzyl)adenine)(chloride)3]
  参考文献：
  名称：

  Diverse in vitro and in vivo anti-inflammatory effects of trichlorido-gold(III) complexes with N6-benzyladenine derivatives

  摘要：

  A series of gold(III) complexes involving differently substituted derivatives of a plant hormone N6-benzyladenine (HL1-5) is reported. The complexes have the general formula [Au(HL1-5)Cl-3]center dot nH(2)O (n = 0 for 1,3-5; and n = 1 for 2), where N6-(2-fluorobenzyl)adenine(HL1), N6-(2-chlorobenzyl)adenine (HL2), N6-(3-chlorobenzyl)adenine (HL3), N6-(4-chlorobenzyl)adenine (HL4) and N6-(4-methylbenzyl)adenine (HL5) represent the N9coordinated ligands. The results of thorough characterization (elemental and thermal analyses, FT-IR, Raman and NMR spectroscopies, ESI+ mass spectrometry, conductivity measurements, OFT calculations) showed that the presented complexes 1-5 involve a central gold(III) atom coordinated in a square-planar geometry by the N9 atom of the purine moiety of HL1-5 and by three chlorido ligands. The complexes (1-5) were studied in vitro for cytotoxicity and anti-inflammatory activity on LPS-activated macrophages (THP-1 cell line), and in vivo for anti-inflammatory effects (1, 2, 5) using the carrageenan-induced hind paw oedema model on rats. Surprisingly, the results on the in vitro level revealed that the complexes show negligible cytotoxicity and anti-inflammatory activity, however, the activity on the in vivo level was found to be significant, fully comparable with the utilized drug Indomethacin, or even better as compared to a gold-containing metallodrug Auranofin. (c) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.02.002
• 作为产物：
  描述：

  2-氟苄胺 、 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-(2-fluorobenzylamino)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。
• [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。
• Investigation of Ag(I) complexes involving 6-(benzylamino)purine derivatives
  作者：Tomáš Šilha、Michal Čajan、Zdeněk Trávníček

  DOI：10.1007/s00706-013-1078-4

  日期：2013.12

  complexes of the general composition [Ag(μ 2 -RBap)]·yH2O} n (y = 0 or 0.5), involving the deprotonated forms of the 6-(benzylamino)purine derivatives (RBap), was prepared. The compounds were characterized by elemental analysis (C, H, N), Raman and FT-IR spectroscopy, TG/DTA thermal analyses, and X-ray powder diffraction. On the basis of the fact that we were not able to prepare single crystals suitable

  摘要一系列银（I）的一般组合物的复合物[银（μ 2 - [R BAP）]· ÿ ħ 2 ö} Ñ（Ý  = 0或0.5），涉及6-（苄基氨基）的去质子化形式的嘌呤制备衍生物（R Bap）。通过元素分析（C，H，N），拉曼光谱和FT-IR光谱，TG / DTA热分析和X射线粉末衍射对化合物进行表征。基于我们无法制备适合X射线分析的单晶这一事实，尽管在不同条件下进行了许多尝试，但DFT计算被用于预测配合物的结构性质。计算结果暗示了 R Bap通过嘌呤部分的N1和N9原子与Ag（I）配体结合，从而形成涉及Ag（N1）（N9）供体的一维聚合物链结构。所选配合物的热分解产物通过扫描电子显微镜与能量色散X射线光谱相结合进行表征，并确定为平均粒径约为10μm的银聚集体。 图形概要
• X-ray structural characterizations of the reaction products between ZnCl2 and 6-benzylaminopurine derivatives in different acidic conditions
  作者：Zdeněk Trávníček、Jaromír Marek

  DOI：10.1016/j.molstruc.2009.06.011

  日期：2009.9

  The reaction between ZnCl2 and the corresponding 6-benzylaminopurine derivative, Ln, [where L1 = 6-(4-fluorobenzylamino)purine, L2 = 6-(2-fluorobenzylamino)purine or L3 = 6-(4-chlorobenzylamino)purine] in 0.1 M or 2 M HCl afforded various products in dependence on a pH of the reaction medium. X-ray structures of the reaction products have been determined by a single crystal X-ray analysis. It has been

  摘要 ZnCl2 与相应的 6-苄氨基嘌呤衍生物 Ln 之间的反应，[其中 L1 = 6-(4-氟苄氨基)嘌呤，L2 = 6-(2-氟苄氨基)嘌呤或 L3 = 6-(4-氯苄氨基)嘌呤]在 0.1 M 或 2 M HCl 中根据反应介质的 pH 值提供各种产物。反应产物的 X 射线结构已通过单晶 X 射线分析确定。已经发现，该反应导致在 0.1 M HCl 中形成 [Zn(HL1)Cl3]·H2O (1)，其中 L1 配体作为单个 N1-H 质子化 N9-H 互变异构体并与 Zn 配位通过嘌呤骨架的 N7 原子。另一方面，在 2 M HCl 中的反应过程中形成了组成为 (H2L2)[ZnCl4]·H2O (2) 和 (H2L3)[ZnCl4] (3) 的离子对化合物。每个有机分子 L2 和 L3 被质子化两次，其正电荷通过 [ZnCl4]2- 阴离子的存在进行补偿。阳离子在 (2) 中以 N1-H、N7-H
• 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。