Cytokinins: Synthesis of 2-, 8-, and 2,8-substituted 6-(3-methyl-2-butenylamino)purines and their relative activities in promoting cell growth |
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Authors: | Laurence G. Dammann Nelson J. Leonard Ruth Y.Schmitz Folke Skoog |
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Affiliation: | School of Chemical Sciences, University of Illinois, Urbana, IL 61801, U.S.A.;Institute of Plant Development, Birge Hall, University of Wisconsin, Madison, WI 53706, U.S.A. |
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Abstract: | We have synthesized 2- and 8-monosubstituted and 2,8-disubstituted derivatives of the cytokinin 6-(3-methyl-2-butenylamino)purine (N6-isopentenyladenine) and have shown the dependence of growth-promoting activity in the tobacco bioassay upon the position, number, and type of substituent. The representative substituent groups were MeS, Me, MeSO2, C6H5CH2S, HS and Cl. The 8-methyl derivative was exceptional in being more active than the unsubstituted parent compound. In general, substitution in the 8-position decreases activity less than substitution in the 2-position, with the exception of the electron-attracting methylsulfonyl. Substitution in both the 2- and 8-positions lowers the activity more than substitution at either single position on the adenine nucleus, with the exception of the 2,8-dimethyl derivative. The chloro and methylthio derivatives show activity in the same range as the methyl derivatives, and the mercapto compounds, which exist mainly as CS tautomers, show somewhat less activity than the corresponding methylthio compounds. Bulky (C6H5CH2S and MeSO2) and strongly electron-attracting (MeSO2) substituents cause relatively great reduction in cytokinin activity. |
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Keywords: | Cytokins 2-, 8- and 2,8-substituted 6-(3-methyl-2-butenylamine) purines relative activity growth activities. |
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