6-N-(2',4'-Dichlorbenzyl)aminopurin | 20366-84-1

• 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-N-(2',4'-Dichlorbenzyl)aminopurin
• 英文别名: (2,4-dichloro-benzyl)-(7(9)H-purin-6-yl)-amine；N-[(2,4-Dichlorophenyl)methyl]-9H-purin-6-amine；N-[(2,4-dichlorophenyl)methyl]-7H-purin-6-amine
• CAS: 20366-84-1
• 化学式: C₁₂H₉Cl₂N₅
• 分子量: 294.143
• InChiKey: AVABYJXKHLOFKV-UHFFFAOYSA-N

物化性质

• 熔点：
  >230 °C
• 沸点：
  441.1±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 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：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲胺 、 6-氯嘌呤 以 二甲基亚砜 为溶剂， 生成 6-N-(2',4'-Dichlorbenzyl)aminopurin
  参考文献：
  名称：

  Specific Interaction of Cytokinins and Their Analogs with Rotenone-sensitive Internal NADH Dehydrogenase in Potato Tuber Mitochondria

  摘要：

  在新鲜土豆块茎（Solarium tuberosum）的线粒体中，研究了细胞分裂素对鱼藤酮敏感的NADH脱氢酶的影响，考虑到先前研究中未充分解释的外部和鱼藤酮不敏感的内部NADH脱氢酶的作用。在亚线粒体颗粒（smp）中，玉米素仅微弱活跃，而玉米素核苷（ZR）则不活跃。异戊烯腺嘌呤（iP）和异戊烯腺苷（iPA）在400 μM时的抑制率分别为45%和30%，而BA（BA）的抑制率为64%。在完整的线粒体中，iP和BA的抑制显著增加，I50分别为50和250 μM，而玉米素和iPA的抑制则降低。结构-活性研究表明，疏水性和立体因素对活性很重要。细胞分裂素通过天然醌抑制电子流动的强度大于通过合成醌的抑制。这些结果表明，在细胞分裂素中，调节电子传输的种类是iP而不是其核苷或玉米素。

  DOI：

  10.1271/bbb.61.1806

文献信息

• Specific Interaction of Cytokinins and Their Analogs with Rotenone-sensitive Internal NADH Dehydrogenase in Potato Tuber Mitochondria
  作者：Masayuki Sue、Hideto Miyoshi、Hajime Iwamura

  DOI：10.1271/bbb.61.1806

  日期：1997.1

  Effects of cytokinins were studied on rotenone-sensitive NADH dehydrogenase in mitochondria from fresh potato tubers (Solarium tuberosum), in consideration of the operation of external and rotenone-insensitive internal NADH dehydrogenases that has not been fully accounted for in previous studies. In submitochondrial particles (smp), zeatin was only weakly active, and zeatin riboside (ZR) was inactive. Inhibition rates at 400 μM of isopentenyladenine (iP) and isopentenyladenosine (iPA) were 45% and 30%, respectively, and that of BA (BA) was 64%. In intact mitochondria, the inhibition by iP and BA significantly increased, I50 being 50 and 250 μM, respectively, but that by zeatin and iPA decreased. A structure–activity study showed that hydrophobic and steric factors are important for the activity. Cytokinins inhibited the electron flow via natural quinone more strongly than that via synthetic quinone. These results suggest that among the cytokinins the species that can regulate the electron transport is iP rather than its riboside or zeatin.

  在新鲜土豆块茎（Solarium tuberosum）的线粒体中，研究了细胞分裂素对鱼藤酮敏感的NADH脱氢酶的影响，考虑到先前研究中未充分解释的外部和鱼藤酮不敏感的内部NADH脱氢酶的作用。在亚线粒体颗粒（smp）中，玉米素仅微弱活跃，而玉米素核苷（ZR）则不活跃。异戊烯腺嘌呤（iP）和异戊烯腺苷（iPA）在400 μM时的抑制率分别为45%和30%，而BA（BA）的抑制率为64%。在完整的线粒体中，iP和BA的抑制显著增加，I50分别为50和250 μM，而玉米素和iPA的抑制则降低。结构-活性研究表明，疏水性和立体因素对活性很重要。细胞分裂素通过天然醌抑制电子流动的强度大于通过合成醌的抑制。这些结果表明，在细胞分裂素中，调节电子传输的种类是iP而不是其核苷或玉米素。
• 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。
• HETEROCYCLIC COMPOUNDS 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：Popa Igor

  公开号：US20080014227A1

  公开（公告）日：2008-01-17

  Novel heterocyclic derivatives based on N 6 -substituted adenine, having anticancer, mitotic, immunosuppressive and antisenescent properties 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-取代腺嘌呤的新型杂环衍生物，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，以及它们的制备方法。还包括含有这些衍生物作为活性化合物的制药组合物、化妆品制剂和生长调节剂，以及使用这些衍生物制备药物、化妆品制剂、生物技术过程、化妆品和农业的方法。
• SUBSTITUTION DERIVATIVES OF N6-BENZYLADENOSINE-5´-MONOPHOSPHATE, METHODS OF PREPARATION THEREOF, USE THEREOF AS MEDICAMENTS, AND THERAPEUTIC PREPARATION CONTAINING THESE COMPOUNDS
  申请人：Univerzita Palackého v Olomouci

  公开号：EP2563801B1

  公开（公告）日：2014-09-24
• HETEROCYCLIC COMPOUND BASED ON N sp 6 /sp −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
  申请人：Ustav Experimentalni Botaniky Akademie ved Ceské Republiky

  公开号：EP1419157A2

  公开（公告）日：2004-05-19