| Project/Area Number |
13660106
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Mie University |
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Principal Investigator |
NISHIKAWA Shiro Mie University, Faculty of Bioresources, Professor, 生物資源学部, 教授 (50024592)
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| Co-Investigator(Kenkyū-buntansha) |
INAGAKI Minoru Mie University, Faculty of Bioresources, Associate Professor, 生物資源学部, 助教授 (20242935)
柏村 直樹 三重大学, 生物資源学部, 教授 (20026412)
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| Project Period (FY) |
2001 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2003: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2002: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2001: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | cytokinin / carbon-substituted analog / 1-dezapurine / Tobacco culls / Amaranthus seedling / Pd coupling / betacyanin / structure-activity-relationship / サイトカイン / 1-デアザプリン / ヒモゲイトウ試験 / ノーデアザプリン / 炭素置換デアザプリン |
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| Research Abstract |
As novel candidates of highly active cytokinins, 1-deazapurine derivatives were designed carefully and synthesized in preparative scale. To compare with the derivatives which have been prepared, some 7-arylethynyl- and 7-alkylethynyl-substituted 1-deazapurines were designed and synthesized. The important intermediate, 7-iodo-l-imidazo[4,5-b]pyrimidine-triacetyl riboside vas subjected to the Sonogashira Coupling with terminal alkynes with various substituents using Pd and Cu as catalysts to yield 7-alkynyl triacetyl-riboside derivatives of 1-deazapurines. The obtained 7-alkynyl triacetyl-ribosides were deprotected by hydrolysis with methanolic ammonia to remove acetyl protective groups. The deprotected ribosides were further hydrolyzed with 1NHC1 to obtain free bases of 7-alkynyl-l-deazapurine derivatives. Six ribosides, and six free bases were finally prepared as novel cytokinin analogs. The obtained 7-alkynykl-riboseides were also subjected to the reaction with sodium methylmercaptane
… More
to yield the Z and E geometrical isomers of 7-alkenyl-l-deazapurine ribosides. Four of five cases of this addition, Z isomers were predominant to the corresponding E isomer; the 1-Naphthyl derivative of alkenyl-ribosides gave an only Z isomer because of the bulkiness of naphthyl substituent. Nine novel derivatives were prepared for this type of 7-alkenyl-derivatives.
The biological activities of the obtained cytokinin analogs were estimated by Tobacco Culls propagation test and Betacyanine formation test with Seedling of Amaranthus Among the compounds with aliphatic substituents on 7-position of 1-deazapurine, the 4-methylpentinyl derivative showed a moderate cytokinin activity. On the other hand, compounds with aromatic substituents showed strong activity in case of 3-methothypenylethynyl and 3-fluorophenylethynyl derivatives. The 3-methothyphenylethynyl derivative was one of the most effective cytokinin analogs, and was almost equivalent and/or more better than the traditional N^6substituted cytokinin, Benzyladenine (BA). Therefore, the introduction of 3-methoxyphenylethynyl substituent at the 7-position of 1-deazapurine ring was revealed as quite effective drug-design for strong cytokinin analogs. Moreover, because the compound has a moderate fluorescence activity, the 3-methoxyphenyleth.tnyl derivative will be useful for mechanistic studies for the incorporation, distribution and degradation of cytokinin within the living plant cell. Less
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