3-[(9H-嘌呤-6-基氨基)甲基]苯酚 | 75737-38-1

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷酸及其类似物
• 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: 3-[(9H-嘌呤-6-基氨基)甲基]苯酚
• 中文别名: 6-(3-羟基苄胺基)嘌呤
• 英文名称: m-topolin
• 英文别名: 6-(3-hydroxybenzylamino)purine；meta-topolin；3-OHBap；3-[(7H-purin-6-ylamino)methyl]phenol
• CAS: 75737-38-1
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: BUDWTFCZGZYQHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  284-286℃
• 沸点：
  458.1±55.0 °C(Predicted)
• 密度：
  1.49
• 溶解度：
  DMF：10mg/mL； DMSO：30mg/mL； DMSO:PBS (pH 7.2) (1:5)：0.16 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

Meta-Topolin（m-Topolin）是一种高活性的芳香细胞分裂素。

体外研究

Meta-Topolin最初从柳树叶中分离出来。它不仅是植物组织中的天然成分，还与其9-β-D-核糖呋喃基和9-β-D-葡萄吡喃糖基衍生物共同存在。在促进植物组织培养中芽的形成方面，Meta-topolin比苯环腺嘌呤（Zeatin）和苄基腺嘌呤更有效。在spathiphyllum floribundum中，含有BAP和Meta-topolin的培养基中的芽生产量非常相似。

反应信息

• 作为反应物：
  描述：

  7-methylguanosine 、 3-[(9H-嘌呤-6-基氨基)甲基]苯酚 在 dipotassium hydrogenphosphate 、 purine nucleotide phosphorylase 作用下， 以 乙醇 、 水 为溶剂， 生成 6-(3-hydroxybenzyl)adenosine
  参考文献：
  名称：

  [15 N4 ] 嘌呤标记的细胞分裂素糖苷的合成，该糖苷来源于具有 9-β-D、7-β-D-吡喃葡萄糖基或 9-β-D-呋喃核糖基团的玉米素和拓扑蛋白

  摘要：

  描述了 [15 N4 ] 嘌呤标记的细胞分裂素糖苷的合成，该糖苷源自玉米素和含有 9-β-d、7-β-d-吡喃葡萄糖基或 9-β-d-呋喃核糖基的玉米黄素。这些 N6 取代的腺嘌呤衍生物旨在作为植物激素分析的内部分析标准。所有标记化合物均由 6-氯[15 N4 ] 嘌呤 (1) 制备。1 与乙酰溴-α-d-葡萄糖的平衡反应得到异构体 7-β-d (3) 和 9-β-d (4) 氯代葡萄糖基前体，用相应的胺处理得到所需的标记细胞分裂素 7- β-d (6) 和 9-β-d (5) 吡喃葡萄糖苷。由 6-氯[15 N4 ] 嘌呤 (1) 制备的细胞分裂素 (7) 通过直接酶促转糖基化反应获得含有 9-β-d-呋喃核糖基团的细胞分裂素 (8)。

  DOI：

  10.1002/jlcr.3702
• 作为产物：
  描述：

  6-(3-hydroxybenzylamino)-9-(tetrahydropyran-2-yl)purine 以 水 为溶剂， 反应 24.0h， 生成 3-[(9H-嘌呤-6-基氨基)甲基]苯酚
  参考文献：
  名称：

  Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives

  摘要：

  In an attempt to improve specific biological functions of cytokinins routinely used in plant micropropagation, 33 6-benzylamino-9-tetrahydropyran-2-ylpurine (THPP) and 9-tetrahydrofuran-2-ylpurine (THFP) derivatives, with variously positioned hydroxy and methoxy functional groups on the benzyl ring, were prepared. The new derivatives were prepared by condensation of 6-chloropurine with 3,4-dihydro-2H-pyran or 2,3-dihydrofuran and then by the condensation of these intermediates with the corresponding benzylamines. The prepared compounds were characterized by elemental analyses, TLC, HPLC, melting point determinations, CI+ MS and H-1 NMR spectroscopy. The cytokinin activity of all the prepared derivatives was assessed in three classical cytokinin bioassays (tobacco callus, wheat leaf senescence and Amaranthus bioassay). The derivatives 6-(3-hydroxybenzylamino)-9-tetrahydropyran-2-ylpurine (3) and 6-(3-hydroxybenzylamino)-9-tetrahydrofuran-2-ylpurine (23) were selected, because of the high affinity of their parent compound meta-topolin (mT, 6-(3-hydroxybenzylamino) purine) to cytokinin receptors, as model compounds for studying their perception by the receptors CRE1/AHK4 and AHK3 in a bacterial assay. Both receptors perceived these two derivatives less well than they perceived the parent compound. Subsequently, the susceptibility of several new derivatives to enzyme degradation by cytokinin oxidase/dehydrogenase was studied. Substitution of tetrahydropyran-2-yl (THP) at the N-9 position decreased the turnover rates of all new derivatives to some extent. To provide a practical perspective, the cytotoxicity of the prepared compounds against human diploid. broblasts (BJ) and the human cancer cell lines K-562 and MCF-7 was also assayed in vitro. The prepared compounds showed none or marginal cytotoxicity compared to the corresponding N-9-ribosides. Finally, the pH stability of the two model compounds was assessed in acidic and neutral water solutions (pH 3-7) by high-performance liquid chromatography (HPLC). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.041

文献信息

• [EN] 6,8-DISUBSTITUTED-9-(HETEROCYCLYL)PURINES, COMPOSITIONS CONTAINING THESE DERIVATIVES AND THEIR USE IN COSMETIC AND MEDICINAL APPLICATIONS<br/>[FR] 9-(HÉTÉROCYCLYL)PURINES 6,8-DISUBSTITUÉES, COMPOSITIONS CONTENANT CES DÉRIVÉS ET LEUR UTILISATION DANS DES APPLICATIONS COSMÉTIQUES ET MÉDICINALES
  申请人：USTAV EX BOTAN AV CR V V I

  公开号：WO2016095880A1

  公开（公告）日：2016-06-23

  6,8-Disubstituted-9-(heterocyclyl) purines which can be used in pharmaceutical and cosmetic compositions and/or applications are provided. These 6,8-disubstituted-9-(heterocyclyl) purines have a wide range of biological activities, including for example antioxidant, anti-inflammatory, anti-senescent, as well as well as other activities which are especially useful in pharmaceutical and cosmetic applications.

  提供可用于制药和化妆品组合物和/或应用的6,8-二取代-9-(杂环基) 嘌呤。这些6,8-二取代-9-(杂环基) 嘌呤具有广泛的生物活性，例如抗氧化、抗炎、抗衰老等，以及其他在制药和化妆品应用中特别有用的活性。
• [EN] MESYLATE SALTS OF HETEROCYCLIC CYTOKININS, COMPOSITIONS CONTAINING THESE DERIVATIVES AND USE THEREOF<br/>[FR] SELS DE MÉSYLATE DE CYTOKININES HÉTÉROCYCLIQUES, COMPOSITIONS CONTENANT CES DÉRIVÉS ET LEUR UTILISATION
  申请人：UNIV PALACKEHO

  公开号：WO2021233485A1

  公开（公告）日：2021-11-25

  Object of the invention are mesylates of heterocyclic cytokinins of general formula I: (I) wherein R is selected from the group comprising C3-C15 cycloalkyl, furfuryl, allyl, 4-hydroxy-3-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 4-hydroxy-3-methylbutyl, 4-hydroxy-1,3-dimethylbut-2-en-1-yl, 4-hydroxy-1,3-dimethylbutyl, benzyl, wherein the cycloalkyl, allyl, benzyl and furfuryl may be unsubstituted or optionally substituted with 1 to 3 substituents selected from the group comprising hydroxy, halogen, methyl, hydroxymethyl and methoxy, and salts, solvates and addition salts therof. These compounds are particularly suitable for agricultural and biotechnological use, and their great advantage is increased water solubility as compared to the corresponding free bases of heterocyclic cytokinins.

  本发明的对象是一般式I的杂环细胞素的甲磺酸盐：（I）其中R选自包括C3-C15环烷基、呋喃基、烯丙基、4-羟基-3-甲基丁-2-烯-1-基、3-甲基丁-2-烯-1-基、4-羟基-3-甲基丁基、4-羟基-1,3-二甲基丁-2-烯-1-基、4-羟基-1,3-二甲基丁基、苄基的群组中，其中环烷基、烯丙基、苄基和呋喃基可以未被取代或者可选择地被1至3个取代基取代，所述取代基选自包括羟基、卤素、甲基、羟甲基和甲氧基的群组，以及其盐、溶剂合物和加合物。这些化合物特别适用于农业和生物技术用途，其主要优点是相对于杂环细胞素的相应游离碱而言具有增加的水溶性。
• [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。
• Method for the selection of genetically transformed cells and compounds for use in the method
  申请人：SANDOZ LTD.

  公开号：EP0530129A1

  公开（公告）日：1993-03-03

  A method for selecting from a population of cells genetically transformed cells into which a desired nucleotide sequence has been introduced, wherein in the transformed cells the desired nucleotide sequence or a co-introduced nucleotide sequence induces or increases a positive effect of a compound or nutrient supplied to the population of cells, thereby allowing the transformed cells to be identified or selected from non-transformed cells, e.g. for the preparation of genetically transformed plants not containing as a selection marker a non-native nucleotide sequence coding for toxin, antibiotic or herbicide resistance; as well as novel glucuronide compounds, including cytokinin glucuronide compounds, for use in the method.

  一种从经遗传转化的细胞群体中选择已引入所需核苷酸序列的细胞的方法，其中在转化的细胞中，所需核苷酸序列或共同引入的核苷酸序列诱导或增加化合物或营养物对细胞群体的正效应，从而允许识别或选择转化的细胞，例如用于制备不含有非天然核苷酸序列编码毒素、抗生素或除草剂抗性的选择标记的遗传转化植物；以及用于该方法的新型葡萄糖醛酸化合物，包括细胞分裂素葡萄糖醛酸化合物。
• [EN] NITROGEN HETEROCYCLIC CYTOKININ DERIVATIVES, COMPOSITIONS CONTAINING THESE DERIVATIVES AND USE THEREOF<br/>[FR] DÉRIVÉS DE CYTOKININE HÉTÉROCYCLIQUES AZOTÉS, COMPOSITIONS CONTENANT CES DÉRIVÉS ET UTILISATION ASSOCIÉES
  申请人：UNIV PALACKEHO

  公开号：WO2022012702A1

  公开（公告）日：2022-01-20

  The invention relates to N2,N6-disubstituted-9-(2-oxacycloalkyl)-9H-purine-2,6-diamine derivatives and their use as prodrugs and in agriculture and biotechnology. The compounds of the present invention exhibit a number of biological activities associated with stress inhibition, especially senescence, growth regulation and yiled formation biological activities. The invention also relates to agricultural and biotechnological compositions containing such derivatives as active agents.

  本发明涉及N2，N6-二取代-9-(2-氧杂环烷基)-9H-嘌呤-2,6-二胺衍生物及其用作前药、农业和生物技术的用途。本发明的化合物表现出许多与抑制应激有关的生物活性，特别是衰老、生长调节和产量形成生物活性。本发明还涉及含有这些衍生物作为活性剂的农业和生物技术组合物。