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Lookup NU author(s): Emeritus Professor Bernard Golding, Professor William Clegg, Dr Mark Elsegood, Professor Roger Griffin
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Methods are described for the preparation of derivatives of the polyamines 1,4-diaminobutane (putrescine), and N′-(3-amihopropyl)-l,4-diaminobutane (spermidine) in which a particular amino group is modified with, e.g., a guanidino function. Specific amino groups in these polyamines were protected as ;V-trifluoroacetyl, and yV-4-azidobenzyloxycarbonyl derivatives, which were unmasked chemoselectively using methanolic ammonia, and dithiothreitol-triethylamine, respectively. Guanidino functions were introduced by an improved procedure in which an amino group was treated with 3,5-dimethyl-Ar-nitro-!//-pyrazole-l-carboximidamide in methanol to give a nitroguanidine derivative, from which the nitro group was removed by catalytic transfer hydrogénation. The methodology is exemplified by the development of efficient preparative routes to agmatine, and hirudonine. The integrity of the sequence of protection/deprotection leading to hirudonine was confirmed by a crystal-structure analysis of its sulfate. The effect of selected compounds on the uptake of putrescine into rat lung cells was determined, and showed that N4-(4-azidobenzyloxycarbonyl)spermidine was the best inhibitor (Ki = 3.4 μM).
Author(s): Golding BT, Mitchinson A, Clegg W, Elsegood MRJ, Griffin RJ
Publication type: Article
Publication status: Published
Journal: Journal of the Chemical Society - Perkin Transactions 1
Year: 1999
Issue: 3
Pages: 349-356
Print publication date: 01/01/1999
ISSN (print): 0300-922X
ISSN (electronic): 1364-5463
Publisher: Royal Society of Chemistry
URL: http://dx.doi.org/10.1039/a806355i
DOI: 10.1039/a806355i
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