55198-39-5Relevant articles and documents
Synthesis and cytotoxicity of some d-mannose click conjugates with aminobenzoic acid derivatives
Hradilová, Ludmila,Poláková, Monika,Dvo?áková, Barbora,Hajdúch, Marián,Petru?, Ladislav
, p. 1 - 6 (2013/01/15)
Two sets of new conjugates obtained from d-mannose derivatives and o-, m-, and p-substituted benzoic acid esters interconnected through a triazole ring were synthesized by Cu(I) catalyzed azide-alkyne cycloaddition. All synthesized compounds were tested for their in vitro cytotoxic activity against seven cancer cell lines with/without multidrug resistance phenotype as well as non-tumor MRC-5 and BJ fibroblasts. Butyl ester of 4-aminobenzoic acid 6c showed the highest activity among all tested compounds, however, it was active only against K562 myeloid leukemia cells. N-Glycosyltriazole conjugates, both acetylated and nonacetylated at mannose moiety, were almost completely inactive. In contrast, some of the acetylated O-glycosyl conjugates showed cytotoxic activity which was cell line dependent and strongly affected by position of benzoic acid substitution as well as a length of its ester alkyl chain; the most potent compound was acetylated mannoside conjugated with octyl ester of m-substituted benzoic acid. However, deacetylation resulting in hydrophilicity increase of the glycosides almost completely abolished their cytotoxic potency.
CONVENIENT SYNTHESIS OF ESTERS OF 2-PYRROLECARBOXYLIC ACID AND OF PYRIDINECARBOXYLIC ACIDS BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT ADDED SOLVENT
Barry, Jean,Bram, Georges,Petit, Alain
, p. 875 - 880 (2007/10/02)
By reaction of aromatic K-carboxylates having nucleophilic N-atom in solid-liquid phase transfer catalysis (PTC) conditions without added solvent (catalyst : tetraalkylammonium halide) with alkylating reagents, the corresponding esters are prepared.By a judicious choice of experimental conditions, the amounts of N-alkylated products can be lowered.From 2-pyrrolecarboxylic acid, the three isomers of pyridinecarboxylic acid and o-aminobenzoic acid, corresponding esters of ethyl, benzyl, n-octyl and n-cetyl, generally are obtained with good yields.