Decomposition of 1-(ω-aminoalkanoyl)guanidines under alkaline conditions

被引：15
作者：
Brennauer, Albert [1 ]
Keller, Max [1 ]
Freund, Matthias [1 ]
Bernhardt, Guenther [1 ]
Buschauer, Armin [1 ]
机构：
[1] Univ Regensburg, Inst Pharm, D-93040 Regensburg, Germany
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 39期
关键词：
acylguanidines; lactam formation; degradation rate; UV spectroscopy;
D O I：
10.1016/j.tetlet.2007.07.147
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The decomposition of some N-G-(omega)-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-(omega)-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 degrees C). In contrast the half life of 1-(6-aminohexanoyl)guanidine is 7.7 h, which is comparable to the hydrolysis of acetylguanidine (t(1/2) = 9.6 h) in alkaline solution. (c) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：6996 / 6999
页数：4
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