In this work, 3-benzothazol-2-yl-phenylamine(1)was synthesized through the reaction of 2-aminothiophenol and 3-
aminobenzoic acid using polyphosphoric acid as dehydrating agent, and used as start for the preparation of the
target compounds IV and V. Benzothiazolyl-phenylamine1was reacted with ethoxymethylene diethyl malonate ester
(EMME) to afford compound II which was thermally cyclized in diphenyl ether to give 7-benzothizol-2-ylquinolone
III. Benzaothiazolylquinolone IV was synthesized from the reflux of 7-benzothizol-2-ylquinolone III with POCl5. The
nucleophillic substitution of chloride anion of 7-benzothizol-2-ylchloroquinolone IVwith p-toluidine was preceded
by using anhydrous potassium carbonate in DMF. Compounds IV and V were screened for antitumor activity
against breast carcinoma cell line (MCF-7). The IC 50% of compounds IV and V were 0.066 and 0.056 umol/mL
respectively and showed high activity in comparison to 0.065 umol/mL standard A . The structure of the compounds
IV and V was confirmed using IR, NMR, mass spectroscopy and elemental analysis. |
