Physical Sciences and Mathematics Commons^™

Synthesis And Leishmanicidal Evaluation Of Novel 4-Substituted-2,2-Dimethyl-7-(Prop-2-Ynyloxy)Chromenes, Babak H. Alizadeh, Alireza Foroumadi, Susan K. Ardestani, Fatemeh Poorrajab, Abass Shafiee

Turkish Journal of Chemistry

Substituted 4-chromenes were synthesized via the Grignard coupling reaction of various substituted phenyl- and benzylmagnesium chlorides with 2,2-dimethyl-7-(prop-2-ynyloxy)chroman-4-one (1) in relatively good yield (60%-85%). The benzylic-substituted derivatives were a mixture of 2 exo and endo regioisomers, and the exo compounds were a mixture of E and Z isomers. Structural analysis of the exo and endo isomers, as well as E and Z of exo isomers were based on H-NMR, ^{13}C-NMR, and NOESY experiments. The synthetic compounds were examined for in vitro activity against Leishmania major and compound 9 (a, b) was the most active, with inhibitory activity of 36%.