Synthesis of some F-heterocyclic compounds of potential anticancer activity using 8-fluoro-1- benzosuberone as a synthon

ABSTRACT

8-fluoro-1-benzosuberone I condensed with aromatic aldehydes in the presence of potassium hydroxide to yield the arylmethylene derrivatives II, which condensed with phenylhydrazinc and thiourea to give the corresponding pyrazol and pyrimidine derivatives III and IV, respectively Compound IV reacted with chloroctic acid, alpha - bromopropionic acid or beta-bromopropionic acid to afford the thiazolopy-rimidine, methylthiazolopyrimia and thiazinopyrimidine derivatives V, VI and VII, respectively. Compound V condensed with aromatic aldehydes to afford the arylmethycine derivativcs VIII. Also, the pyrano and pyridino-fluorobenzosubcronc derivatives IX and X were synthesized. The obtained products were preliminarily tested as anticancer agents and it was found that the products IIa, IIb, IXa, IXb and X showed promising activity against non-small cell lung cancer