6-furfurylamino-9-(2-chloroethyl)purine | 120593-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 6-furfurylamino-9-(2-chloroethyl)purine
• 英文别名: 9-(2-chloroethyl)-N-(furan-2-ylmethyl)purin-6-amine
• CAS: 120593-23-9
• 化学式: C₁₂H₁₂ClN₅O
• 分子量: 277.713
• InChiKey: VHLJKGNGSIBAPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-溴-2-氯乙烷 、 6-糠氨基嘌呤 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以80%的产率得到6-furfurylamino-9-(2-chloroethyl)purine
  参考文献：
  名称：

  [EN] USE OF 6 - SUBSTITUTED 9 - HALOGENALKYL PURINES FOR REGULATION OF GROWTH AND DEVELOPMENT OF WHOLE PLANTS, PLANT CELLS AND PLANT ORGANS; NOVEL 6 - SUBSTITUTED 9 -HALOGENALKYL PURINES
  [FR] UTILISATION DE PURINES 9-HALOGÉNOALKYLE SUBSTITUÉES EN POSITION 6 DESTINÉES POUR RÉGULER LA CROISSANCE ET LE DÉVELOPPEMENT DE PLANTES ENTIÈRES, DE CELLULES VÉGÉTALES ET D'ORGANES VÉGÉTAUX, NOUVELLES PURINES 9-HALOGÉNOALKYLE SUBSTITUÉES EN POSITION 6

  摘要：

  本发明涉及一般式I的6-取代9-卤代烷基嘌呤衍生物，其中R6选自羟基呋喃基，-NH-(4-羟基-3-甲基丁-2-烯-1-基)，-NH-(3-甲基丁-2-烯-1-基)，-NH-(4-羟基-3-甲基丁基)，-NH-(4-羟基-1,3-二甲基丁-2-烯-1-基)，-NH-(4-羟基-1,3-二甲基丁基)，-NH-苄基，-NH-苯基，其中苄基，呋喃基和苯基可以未取代或选自羟基，卤素，甲基和甲氧基中的1至3个取代基，R9选自C1-C3烷基或C1-C3烯基，其中每个基都取代一个或多个卤素原子，用于调节植物细胞、器官和/或整个植物的生长和发育。本发明还涉及含有这些衍生物的制剂以及新的6-取代9-卤代烷基嘌呤。

  公开号：

  WO2012031574A1

文献信息

• USE OF 6- SUBSTITUTED 9 - HALOGENALKYL PURINES FOR REGULATION OF GROWTH AND DEVELOPMENT OF WHOLE PLANTS, PLANT CELLS AND PLANT ORGANS; NOVEL 6 - SUBSTITUTED 9 - HALOGENALKYL PURINES
  申请人：Mik Vaclav

  公开号：US20130210632A1

  公开（公告）日：2013-08-15

  The invention relates to 6-substituted 9-halogenalkyl purine derivatives of the general formula I wherein R6 is selected from the group comprising —NH-furfuryl, —NH-(4-hydroxy-3-methylbut-2-en-1-yl), —NH-(3-methylbut-2-en-1-yl), —NH-(4-hydroxy-3-methylbutyl), —NH-(4-hydroxy-1,3-dimethylbut-2-en-1-yl), —NH-(4-hydroxy-1,3-dimethylbutyl), —NH-benzyl, —NH-phenyl, wherein benzyl, furfuryl and phenyl can be unsubstituted or optionally substituted with 1 to 3 substituents selected from the group comprising hydroxy, halogen, methyl and methoxy, and R9 is selected from the group comprising C 1 -C 3 alkyl or C 1 -C 3 alkenyl wherein each of the groups is substituted with one or more halogen atoms, for use in the regulation of growth and development of plant cells, organs and/or whole plants. The invention also relates to preparations containing these derivatives and to novel to 6-substituted 9-halogenalkyl purines.

  本发明涉及一般式I的6-取代的9-卤代烷基嘌呤衍生物，其中R6选自包括—NH-呋喃基，—NH-(4-羟基-3-甲基丁-2-烯-1-基)，—NH-(3-甲基丁-2-烯-1-基)，—NH-(4-羟基-3-甲基丁基)，—NH-(4-羟基-1,3-二甲基丁-2-烯-1-基)，—NH-(4-羟基-1,3-二甲基丁基)，—NH-苄基，—NH-苯基，其中苄基，呋喃基和苯基可以是未取代的或可选地取代的，取代基选自羟基、卤素、甲基和甲氧基，R9选自包括C1-C3烷基或C1-C3烯基，其中每个基都取代有一个或多个卤素原子，用于调节植物细胞、器官和/或整个植物的生长和发育。本发明还涉及含有这些衍生物的制剂以及新的6-取代的9-卤代烷基嘌呤。
• Use of 6-substituted 9-halogenalkyl purines for regulation of growth and development of whole plants, plant cells and plant organs; novel 6-substituted 9-halogenalkyl purines
  申请人：Mik Vaclav

  公开号：US09220269B2

  公开（公告）日：2015-12-29

  The invention relates to 6-substituted 9-halogenalkyl purine derivatives of the general formula I wherein R6 is selected from the group comprising —NH-furfuryl, —NH-(4-hydroxy-3-methylbut-2-en-1-yl), —NH-(3-methylbut-2-en-1-yl), —NH-(4-hydroxy-3-methylbutyl), —NH-(4-hydroxy-1,3-dimethylbut-2-en-1-yl), —NH-(4-hydroxy-1,3-dimethylbutyl), —NH-benzyl, —NH-phenyl, wherein benzyl, furfuryl and phenyl can be unsubstituted or optionally substituted with 1 to 3 substituents selected from the group comprising hydroxy, halogen, methyl and methoxy, and R9 is selected from the group comprising C1-C3 alkyl or C1-C3 alkenyl wherein each of the groups is substituted with one or more halogen atoms, for use in the regulation of growth and development of plant cells, organs and/or whole plants. The invention also relates to preparations containing these derivatives and to novel to 6-substituted 9-halogenalkyl purines.

  本发明涉及一般式I的6-取代9-卤代烷基嘌呤衍生物，其中R6选自包括—NH-呋喃基，—NH-（4-羟基-3-甲基丁-2-烯-1-基），—NH-（3-甲基丁-2-烯-1-基），—NH-（4-羟基-3-甲基丁基），—NH-（4-羟基-1,3-二甲基丁-2-烯-1-基），—NH-（4-羟基-1,3-二甲基丁基），—NH-苄基，—NH-苯基，其中苄基、呋喃基和苯基可以未取代或选择性地取代1至3个取代基，所述取代基选自羟基、卤素、甲基和甲氧基，R9选自包括C1-C3烷基或C1-C3烯基，其中每个基都取代有一个或多个卤素原子，用于调节植物细胞、器官和/或整个植物的生长和发育。本发明还涉及含有这些衍生物的制剂和新的6-取代9-卤代烷基嘌呤。
• 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.
• Ramzaeva, N. P.; Lidak, M. Yu.; Gol'dberg, Yu. Sh., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 5, p. 984 - 987
  作者：Ramzaeva, N. P.、Lidak, M. Yu.、Gol'dberg, Yu. Sh.、Shimanskaya, M. V.

  DOI：——

  日期：——
• USE OF 6 - SUBSTITUTED 9 - HALOGENALKYL PURINES FOR REGULATION OF GROWTH AND DEVELOPMENT OF WHOLE PLANTS, PLANT CELLS AND PLANT ORGANS; NOVEL 6 - SUBSTITUTED 9 -HALOGENALKYL PURINES
  申请人：Univerzita Palackého v Olomouci

  公开号：EP2613631A1

  公开（公告）日：2013-07-17