(Isocoumarin-3-yl)phenoxyacetic acids in the amino acid derivatives synthesis. Structure and activity

Title(Isocoumarin-3-yl)phenoxyacetic acids in the amino acid derivatives synthesis. Structure and activity
Publication TypeJournal Article
Year of Publication2017
AuthorsShilin, SV, Shablykina, OV, Ishchenko, VV, Khylia, VP
Abbreviated Key TitleDopov. Nac. akad. nauk Ukr.
DOI10.15407/dopovidi2017.01.082
Issue1
SectionChemistry
Pagination82-87
Date Published1/2017
LanguageUkrainian
Abstract

The relative reactivities of (isocoumarin-3-yl)- and (3,4-dihydroisocoumarin-3-yl)phenoxyacetic acids in the synthesis of amino acid derivatives, which includes the activated N-hydroxysuccinimide esters producing, are studied. It is found that, for the compounds with unsaturated isocoumarin cycle, the rate of activated ester formation is significantly reduced, when a substituent (regardless of size) in the ortho position to the oxyacetic acid fragment appears. While the slowing interaction of their saturated analogues with N-hydroxysuccinimide is not observed due to the presence of the ortho substituent.

Keywords(3, (isocoumarin-3-yl)phenoxyacetic acids, 4-dihydroisocoumarin-3-yl)phenoxyacetic acids, activated ester method, amino acid derivatives, N-hydroxysuccinimide
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