Decomposition of 1-(ω-aminoalkanoyl)guanidines under alkaline conditions |
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Authors: | Albert Brennauer |
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Affiliation: | University of Regensburg, Institute of Pharmacy, Universitätsstr. 31, D-93040 Regensburg, Germany |
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Abstract: | The decomposition of some NG-(ω-aminoalkanoyl)argininamides, which are key intermediates for the preparation of radiolabeled and fluorescent neuropeptide Y receptor ligands, prompted us to synthesize a small series of simple 1-(ω-aminoalkanoyl)guanidines, and to investigate these model compounds for stability in alkaline buffers. The degradation of acylguanidines was monitored by time resolved UV spectroscopy. The most labile compound, 1-(5-aminopentanoyl)guanidine, decomposed with a half life of 19 s to yield piperidin-2-one (pH 10.4 at 25 °C). In contrast the half life of 1-(6-aminohexanoyl)guanidine is 7.7 h, which is comparable to the hydrolysis of acetylguanidine (t1/2 = 9.6 h) in alkaline solution. |
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Keywords: | Acylguanidines Lactam formation Degradation rate UV spectroscopy |
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