Cyclic hydroxamic acids derived from α-amino acids 1. Regioselective synthesis, structure, NO-donor and antimetastatic activities of spirobicyclic hydroxamic acids derived ... View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2010-01

AUTHORS

I. V. Vystorop, N. P. Konovalova, Yu. V. Nelyubina, V. N. Varfolomeev, B. S. Fedorov, T. E. Sashenkova, E. N. Berseneva, K. A. Lyssenko, R. G. Kostyanovsky

ABSTRACT

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. More... »

PAGES

127-135

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-010-0055-x

DOI

http://dx.doi.org/10.1007/s11172-010-0055-x

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1039716005


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