6-(2,3-dihydroxybenzylamino)-9-(tetrahydropyran-2-yl)purine | 1144854-45-4

• 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-(2,3-dihydroxybenzylamino)-9-(tetrahydropyran-2-yl)purine
• 英文别名: 3-[[[9-(oxan-2-yl)purin-6-yl]amino]methyl]benzene-1,2-diol
• CAS: 1144854-45-4
• 化学式: C₁₇H₁₉N₅O₃
• 分子量: 341.37
• InChiKey: VJXDPFWAUJYGFM-UHFFFAOYSA-N

物化性质

• 沸点：
  635.3±65.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 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：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-氨基甲基邻苯二酚 、 6-氯-9-(四氢-2-吡喃基)嘌呤 在 三乙胺 作用下， 以 丙醇 、 正丁醇 为溶剂， 反应 3.0h， 以60%的产率得到6-(2,3-dihydroxybenzylamino)-9-(tetrahydropyran-2-yl)purine
  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

• 6,9-Disubstituted Purine Derivatives and Their Use as Cosmetics and Cosmetic Compositions
  申请人：Szucova Lucie

  公开号：US20090170879A1

  公开（公告）日：2009-07-02

  Certain 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are provided. These 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are useful in compositions for treating mammalian cells, and especially human skin cells, in order to ameliorate the adverse effects of aging, treat skin disease states, treat immunological responses resulting from or associated with inflammation, and the like.

  提供了某些6,9-二取代嘌呤衍生物及其药学上可接受的盐。这些6,9-二取代嘌呤衍生物及其药学上可接受的盐在组合物中对于治疗哺乳动物细胞，尤其是人类皮肤细胞，以缓解衰老的不良影响，治疗皮肤疾病状态，治疗由炎症引起或与之相关的免疫反应等方面非常有用。
• 6,9-disubstituted purine derivatives and their use as cosmetics and cosmetic compositions
  申请人：Institute of Experimental Botany, Academy of Sciences of the Czech Republic

  公开号：US07960397B2

  公开（公告）日：2011-06-14

  Certain 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts of the following general formula are provided wherein R6 and R9 are as defined in the specification. These 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are useful in compositions for application to mammalian cells, and especially human skin cells, in order to improve the cosmetic appearance of the mammalian cells, especially human skin.

  本发明提供了以下一般式的某些6,9-二取代嘌呤衍生物及其药学上可接受的盐，其中R6和R9如规范中定义。这些6,9-二取代嘌呤衍生物及其药学上可接受的盐在组合物中对哺乳动物细胞，尤其是人类皮肤细胞的应用中非常有用，以改善哺乳动物细胞，尤其是人类皮肤的美容外观。
• 6, 9-Disubstituted Purine Derivatives and Their Use as Cosmetics and Cosmetic Compositions
  申请人：Szucova Lucie

  公开号：US20110230503A1

  公开（公告）日：2011-09-22

  Certain 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are provided. These 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are useful in compositions for treating mammalian cells, and especially human skin cells, in order to ameliorate the adverse effects of aging, treat skin disease states, treat immunological responses resulting from or associated with inflammation, and the like.

  提供了某些6,9-二取代嘌呤衍生物及其药学上可接受的盐。这些6,9-二取代嘌呤衍生物及其药学上可接受的盐在组合物中用于治疗哺乳动物细胞，特别是人类皮肤细胞，以改善衰老的不良影响，治疗皮肤疾病状态，治疗由炎症引起或与之相关的免疫反应等。
• 6, 9-disubstituted purine derivatives and their use as cosmetics and cosmetic compositions
  申请人：Szucova Lucie

  公开号：US08575182B2

  公开（公告）日：2013-11-05

  Certain 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts of the general formula are provided wherein R6 and R9 are as defined in the specification. These 6,9-disubstituted purine derivatives and their pharmaceutically acceptable salts are useful in compositions for treating mammalian cells, and especially human skin cells, in order to ameliorate the adverse effects of aging, treat skin disease states, treat immunological responses resulting from or associated with inflammation, and the like.

  提供了一些6,9-二取代嘌呤衍生物及其药学上可接受的盐的普遍公式，其中R6和R9如规范中所定义。这些6,9-二取代嘌呤衍生物及其药学上可接受的盐在组合物中用于治疗哺乳动物细胞，特别是人类皮肤细胞，以改善衰老的不良影响，治疗皮肤疾病状态，治疗由炎症引起或与之相关的免疫反应等。
• 6,9-DISUBSTITUTED PURINE DERIVATIVES AND THEIR USE AS COSMETICS AND COSMETIC COMPOSITIONS
  申请人：Institute of Experimental Botany, Academy of Sciences of the Czech Republic

  公开号：EP2245031B1

  公开（公告）日：2014-02-26