2000年6月
Synthesis and cytokinin activity of fluorescent 7-phenylethynylimidazo[4,5-b]pyridine and its riboside
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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- 巻
- 48
- 号
- 6
- 開始ページ
- 2559
- 終了ページ
- 2564
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jf0000225
- 出版者・発行元
- AMER CHEMICAL SOC
7-Phenylethynylimidazo[4,5-b]pyridine and its riboside have been newly developed as fluorescent carbon-substituted cytokinin analogues. Palladium-catalyzed coupling of 7-iodo-3-(tri-O-acetyl-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine with phenylacetylene followed by ammonolysis afforded the 7-phenylethynyl riboside via its tri-O-acetate. Acid hydrolysis of the riboside provided its free base, which showed a marked enhancement in fluorescence intensity in an aqueous alkaline solution. The free base and its riboside were more active than the corresponding 6-phenylethynylpurine and its riboside, respectively, in Amaranthus betacyanin and tobacco callus bioassays. Surprisingly, the imidazo[4,5-b]pyridine base exhibited strong cytokinin activity comparable to that of NG-benzyladenine in the tobacco callus bioassay. This compound would be useful for studying localization and transport of cytokinins in cells or tissues of plants.
- リンク情報
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- DOI
- https://doi.org/10.1021/jf0000225
- CiNii Articles
- http://ci.nii.ac.jp/naid/80011839211
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/10888584
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000087782500099&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/jf0000225
- ISSN : 0021-8561
- CiNii Articles ID : 80011839211
- PubMed ID : 10888584
- Web of Science ID : WOS:000087782500099