Abstract
3-(p-Chlorophenyl)-1-(2'-naphthyl)-2,3-epoxypropanone (2) is an important intermediate for the synthesis of a variety of different heterocyclic compounds with novel cyclic system. Compound 2 reacted with hydrazine hydrate, phenyl hydrazine, hydroxylamine hydrochloride as nitrogen nucleophiles to afford compounds 3-5, and with carbon disulfide and phenylisocyanate as a carbon electrophile to afford compounds 6 and 7. Furthermore, 6-(4-chlorophenyl) -2-hydrazino -4- naphthaline- 2-yl- 1,6- dihydro - pyrimidin-5-one(8) reacted with p-chlorobenzaldehyde to give Schiff base9 which on cyclocondensation with thioglycolic acid affording compound 10. The new compounds 11-13 were synthesizedby the reaction of compound 8 with carbon disulfide, malononitrile and phenyl isothiocyanate. Also compound 8 reacted with aliphatic acid namely: acetic and formic acids and with sodium nitrite to give triazolopyrimidinones14, 15 and tetrazolopyrimidinone16. A novel series of acyclicnucleosides17a, b were synthesized by utilizing compound 8. Most of the tested compounds showed potent cytotoxic activity. However two compounds, 6 and 16, showed cytotoxic activity very close to that of the Doxorubicin as a reference drug against breast carcinoma cell line MCF-7. Also some synthesized compounds were screened for their antimicrobial activity. Among the assayed compounds derivatives 9 and 17a showed the highest antimicrobial activity.