Synthesis of novel tetrahydronaphthalen-2-yl thiazoles of expected anticancer activity

ABSTRACT

In the present investigation. a variety of tetrahydronaphthyl thiazole derivatives were prepared. The parent compound 4-[5,6,7,8-tetrahydro-2-naphthyl]-2-aminothiazole [l] was allowed to react with isocyanates and isothiocyanates to give substituted ureas or thioureas Ila-f with acid anhydrides to give thiazolyl-pyrrolidinedione IIIa-c. with alkylhalides or aryl sulphonyl chlorides to give the N-substituted derivatives lVa-d with urethane to give N-substituted urea V. with carbon disulphide to give isothiocyanate derivatives VI, with alpha-halocarbonyl compounds to give Vlla-d and with malononitrile to give VIII. Moreover, compound VIId was allowed to react with potassium thiocymatc to give thiamlidinone derivatives X, with semicarbazidc and thiosemicarhztzidc to give Xla,b. with thioglycolic acid to give thiomorpholincdione derivative XII. with malononitrilc to give pyrrole carbonitrilc XIII and with different secondary amines to give acetamido derivatives XlVa-d. Also compound llc reacted with chloroacetic acid. malonic acid and or phenacyl bromide to give the corresponding derivatives XV, XVI and XVII respectivly. Compounds lVa, Vllb and X are effective on both liver carcinoma cell line HePG2 and brain carcinoma cell line U25I while compounds llc, Vlld and VIII are effective on HePG2 only