Organic Chemistry: Current Research
Open Access

Abstract

3',5'-Dibromo-2',4'-dihydroxy Substituted Chalcones: Synthesis and in vitro Trypanocidal Evaluation

K. L. Ameta, Nitu S. Rathore, Biresh Kumar, Edith S. Maalaga M, Manuela Veraastegui and Robert H. Gilman

A new series of 3′, 5′-dibromo-2′, 4′-dihydroxy substituted chalcones was synthesized by the classical Claisen- Schmidt condensation of 3, 5-dibromo-2, 4-dihydroxyacetophenone and variously substituted aromatic aldehydes via conventional as well as non-conventional inorganic solid supported microwave irradiation methods. The non- conventional methodology, has the advantages of being rapid, eco-friendly, easy to handle, requiring shorter reaction time, and quite general. All newly synthesized compounds were evaluated for their inhibitory effect against Trypanosoma cruzi (Chagas disease). Compounds 3c, 3g and 3m showed 85.53, 85.03 and 83.34 in-vitro percentage growth of inhibition respectively; while compounds 3b, 3e, 3i and 3l showed 71.23, 71.95, 67.53 and 68.88 percentage growth of inhibition respectively with nifurtimox and benznidazole as reference drugs. 3l was the compound with a good anti-trypanocidal activity, the lower cytotoxicity, higher therapeutic index 14.5, and was the best candidate in comparison with the others. The structures of the newly synthesized compounds (3a-t) were determined by elemental analysis, FTIR, 1H-NMR, 13C-NMR and mass spectroscopic studies.