Synthesis and Bioevaluation Study of Benzofuran Linked Tetralones as Antimitotic Agent
Chemical Science Transactions
A series of new benzofuran linked tetralones (5a-h) have been prepared by chalcone route of Claisen-Schmidt condensation reaction in the presence of sodium hydroxide, 1-(benzofuran-6-yl)ethanone (1) reacts with substituted benzaldehyde (2a-h) followed by cyclopropanation of 1-(benzofuran-6-yl)-3-phenylprop-2-en-1-one (3a-h) with trimethylsulfoxonium iodide (TMSOI) in the presence of sodium hydride and Friedel-Craft's intramolecular cyclization reaction of
... enylcyclopropyl)methanone (4a-h) in the presence of anhyd. stannic chloride and acetic anhydride. The target molecules were characterized by spectral and elemental analysis and also screened for their antimitotic activity by onion root method. Taken together, our results indicated that among the entire synthesized analogues, the two new compounds 5e and 5f bearing electron donating methoxy group on para and 3,4,5-position of the phenyl moiety respectively exhibits even good antimitotic activity than other compounds. etopophos which are more potent antitumor agents than 4'-o-demethylepipodophyllotoxin. These have been approved for many years for clinical use in the treatment of various types of cancers (breast, testicular, small cell lung cancer, lymphomas, Kaposi's sarcoma, nonlymphocytic leukemia) 10-13 . On the other hand heterocyclic rings and in particular, the benzofuran is an important moiety for the synthesis of pharmaceutical compounds with different activities and good safety profiles. Benzofurans have been drawn as promising structural units in the field of medicinal chemistry. Benzofuran derivatives are a class of most important heterocyclic moieties, which have drawn considerable attention over past year. Benzofuran is known to possess important biological properties and potential applications 14 . Natural and synthetic compounds containing benzofuran fragment displaying a broad range of biological activities such as antimicrobials, anti-inflammatory and analgesic 15 , anticancer 16 , antioxidant agents 17 , antitumor 18 , antitubercular 19,20 and anti-inflammatory 21 .