Cyclic hydroxamic acids derived from α-amino acids 1. Regioselective synthesis, structure, NO-donor and antimetastatic activities of spirobicyclic hydroxamic acids derived from glycine and DL-alanine

Autor: Yu. V. Nelyubina, Fedorov Boris S, E. N. Berseneva, Nina P. Konovalova, T. E. Sashenkova, Konstantin A. Lyssenko, V. N. Varfolomeev, Remir G. Kostyanovsky, I. V. Vystorop
Rok vydání: 2010
Předmět:
Zdroj: Russian Chemical Bulletin. 59:127-135
ISSN: 1573-9171
1066-5285
DOI: 10.1007/s11172-010-0055-x
Popis: The reactions of glycine hydroxamic and DL-alanine hydroxamic acids with triacetonamine are chemoselective and afford 1-hydroxy-7,7,9,9-tetramethyl-1,4,8-triazaspiro[4.5]decan-2-one (3) and (±)-1-hydroxy-3,7,7,9,9-pentamethyl-1,4,8-triazaspiro[4.5]decan-2-one (4), respectively. The X-ray diffraction study showed that compound 3 crystallizes as a solvate with MeCN (1: 1). As shown by ESR measurements, spiro hydroxamic acids 3 and 4 are NO donors in in vitro biological systems. The NO-donor activity of compounds 3 and 4 was found to be substantially higher in the presence of DMSO. Homologue 4 is a stronger NO donor than 3. Compound 4 also exhibits high antimetastatic activity (81%) on the B16-melanoma model.
Databáze: OpenAIRE
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