Babak H. ALIZADEH, Alireza FOROUMADI, Sussan K. ARDESTANI

8091

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

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, 13C-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%.
Anahtar Kelimeler:

Synthesis, chromene, leishmanicidal activity

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

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, 13C-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,

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Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
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