9-(1-乙氧基乙基-1)-6-氯嘌呤 | 33441-77-9

• 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: 9-(1-乙氧基乙基-1)-6-氯嘌呤
• 英文名称: 9-(1-Ethoxyethyl-1)-6-chloropurine
• 英文别名: 6-chloro-9-(1-ethoxyethyl)purine；6-chloro-9-(1-ethoxy-ethyl)-9H-purine；6-Chloro-9-(1-ethoxyethyl)purin
• CAS: 33441-77-9
• 化学式: C₉H₁₁ClN₄O
• 分子量: 226.666
• InChiKey: IUVULVSXWWAKTG-UHFFFAOYSA-N

物化性质

• 熔点：
  49 °C
• 沸点：
  344.3±52.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(1-乙氧基乙基-1)-6-氯嘌呤 以 盐酸 、 水 为溶剂， 生成 6-氯嘌呤
  参考文献：
  名称：

  6-取代的9-（2-脱氧-β-d-异戊-呋喃呋喃糖基）嘌呤及其9-（1-烷氧乙基）对应部分的酸性水解：动力学和机理。1个

  摘要：

  已经在不同浓度的氧离子下测量了几种6-取代的9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤和9-（1-烷氧基乙基）嘌呤的水解速率常数。解释了改变烷氧基极性性质对未取代的9-（1-烷氧基乙基）嘌呤水解的影响，这表明该反应是通过质子化碱部分的限速离去并伴随形成一个烷氧基乙基氧碳鎓离子。通过比较6-取代基对这些化合物及其9-（1-烷氧基乙基）反应剂的反应性的影响，将相同的机理应用于9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤的水解。 -部分。当2'-脱氧腺苷水解后进行1 H NMR光谱。

  DOI：

  10.1016/s0040-4020(01)90052-3
• 作为产物：
  描述：

  乙烯基乙醚 、 6-氯嘌呤 在 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 9-(1-乙氧基乙基-1)-6-氯嘌呤
  参考文献：
  名称：

  N9取代的N 6 -[（3-甲基丁-2-烯-1-基）氨基]嘌呤衍生物及其在某些细胞分裂素生物测定中的生物学活性

  摘要：

  合理的设计是评估信号分子（例如细胞分裂素衍生物）特定活性的最新方法之一。一系列N 6 -[（3-甲基丁-2-烯-1-基）氨基]嘌呤（iP）衍生物，在嘌呤部分的N9原子上被四氢吡喃-2-基，乙氧基乙基和C2-C4烷基特异性取代制备了由各种官能团终止的链。这种合理设计的原因是揭示iP嘌呤部分N9原子处的特异性取代与所制备化合物的细胞分裂素活性之间的关系。合成可以通过最初由6-氯嘌呤制备的6-氯-9-取代的中间体进行，也可以通过将N 6的N9原子直接烷基化来进行-[（3-甲基丁-2-烯-1-基）氨基]嘌呤。在制备化合物N 6 -[（3-甲基丁-2-烯-1-基）氨基] -9-（2-氨基乙基-氨基）嘌呤（12）时，进行选择性还原反应。在温和的条件下，用锌粉还原了-2-（-2--1--1-基）氨基] -9-（2-叠氮基乙基）嘌呤（7）。通过C，H，N元素分析，薄层色谱（TLC），高效液相色谱（HPLC），熔点测定（mp），CI

  DOI：

  10.1016/j.bmc.2011.09.052

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：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。
• Loennberg, Harri; Lehikoinen, Pertti; Neuvonen, Kari, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 10, p. 707 - 712
  作者：Loennberg, Harri、Lehikoinen, Pertti、Neuvonen, Kari

  DOI：——

  日期：——
• N9-substituted derivatives of kinetin: Effective anti-senescence agents
  作者：Václav Mik、Lucie Szüčová、Mária Šmehilová、Marek Zatloukal、Karel Doležal、Jaroslav Nisler、Jiří Grúz、Petr Galuszka、Miroslav Strnad、Lukáš Spíchal

  DOI：10.1016/j.phytochem.2011.02.002

  日期：2011.6

  The first isolated cytokinin, 6-furfurylaminopurine (kinetin or Kin), was identified almost 55 years ago. Its biological effects on plant cells and tissues include influences on such processes as gene expression, cell cycle, chloroplast development, chlorophyll biosynthesis, stimulation of vascular development, delay of senescence, and mobilization of nutrients. In the present study we prepared a series of eight N9-substituted Kin derivatives, and characterized them with available physicochemical methods such as Cl+ mass spectrometry and H-1 NMR spectroscopy. All compounds were tested in three classical cytokinin bioassays: a tobacco callus assay, an Amaranthus assay, and a senescence assay with excised wheat leaves. The ability of the compounds to interact with Arabidopsis cytokinin receptors CRE1/AHK4 and AHK3 was tested in a bacterial receptor assay. Prepared derivatives with certain substitutions of the N9-atom of the purine moiety enhanced the cytokinin activity of the parent compound in the bioassays to a remarkable degree but negatively affected its perception by CRE1/AHK4 and AHK3. The ability of compounds to delay the senescence of excised wheat leaves in both dark and light conditions, was highly correlated with their ability to influence membrane lipid peroxidation, which is a typical symptom of senescence. Our results were corroborated by gene expression profiling of those genes involved in cytokinin metabolism and perception, plant senescence, and the stress response, and suggest that prepared kinetin derivatives might be used as potent anti-senescence agents. (C) 2011 Elsevier Ltd. All rights reserved.
• Purinenucleoside analogs. 2. 9-(1-Alkoxyethyl-1)-6-substituted purines
  作者：M. A. Madre、R. A. Zhuk、M. Yu. Lidak

  DOI：10.1007/bf00515005

  日期：1986.3