Synthesis and Leishmanicidal Evaluation of Novel 4-Substituted-2,2-Dimethyl-7-(prop-2-ynyloxy)Chromenes

Authors

BABAK H. ALIZADEH
ALIREZA FOROUMADI
SUSAN K. ARDESTANI
FATEMEH POORRAJAB
ABASS SHAFIEE

DOI

10.3906/kim-0810-34

Abstract

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%.

Keywords

Synthesis, chromene, leishmanicidal activity

First Page

47

Last Page

58

Recommended Citation

ALIZADEH, BABAK H.; FOROUMADI, ALIREZA; ARDESTANI, SUSAN K.; POORRAJAB, FATEMEH; and SHAFIEE, ABASS (2009) "Synthesis and Leishmanicidal Evaluation of Novel 4-Substituted-2,2-Dimethyl-7-(prop-2-ynyloxy)Chromenes," Turkish Journal of Chemistry: Vol. 33: No. 1, Article 5. https://doi.org/10.3906/kim-0810-34
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss1/5