Keywords
calixresorcinols
click reaction
condensation
cytotoxicity
diastereoisomers
methanesulfonate
triazole
Abstract
Acid-catalyzed condensation of resorcinol, 2-methylresorcinol, and pyrogallol with 2-(4-formylphenoxy)ethyl methanesulfonate in a CHCl3/CF3CO2H or MeOH/HClconc medium led to new rccc and rctt calix[4]resorcinol diastereomers bearing methanesulfonate fragments in high yields, with diasteromeric ratio depending on the nature of the solvent and acid used, as well as their proportions. The obtained compounds can be easily O-alkylated with propargyl bromide, and the subsequent click reaction with BnN3 afforded new multi-functionalized triazole-containing derivatives. Screening against some cancerous and normal cell lines revealed a leading compound, rccc pyrogallol derivative, which exhibited cytotoxic activity against M-HeLa cancer cells at the level of the reference drug Sorafenib.
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