Brennauer, Albert and Keller, Max and Freund, Matthias and Bernhardt, Guenther and Buschauer, Armin (2007) Decomposition of 1-(omega-aminoalkanoyl)guanidines under alkaline conditions. TETRAHEDRON LETTERS, 48 (39). pp. 6996-6999. ISSN 0040-4039,
Full text not available from this repository. (Request a copy)Abstract
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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | INHIBITORS; ACYLGUANIDINES; GUANIDINIUM; BINDING; DESIGN; POTENT; acylguanidines; lactam formation; degradation rate; UV spectroscopy |
| Subjects: | 600 Technology > 615 Pharmacy |
| Divisions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Dec 2020 11:29 |
| Last Modified: | 01 Dec 2020 11:29 |
| URI: | https://pred.uni-regensburg.de/id/eprint/32199 |
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