ABSTRACT
Some naphtho[1,2-b]furan, furo[2,3-f], furo[2,3-g] and furo[3,2-g]quinoline derivatives have been submitted to in vitro cytotoxic tests towards L 1210, MDA-MB 231 and PC3 cell lines. Among them, the furoquinone structures exhibited the most interesting IC50 values.
Subject(s)
Antineoplastic Agents/chemical synthesis , Furans/chemical synthesis , Naphthalenes/chemical synthesis , Quinolones/chemical synthesis , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , Furans/pharmacology , Humans , Naphthalenes/pharmacology , Quinolones/pharmacology , Tumor Cells, CulturedABSTRACT
The synthesis of dihydro furonaphth[1,3]oxazine derivatives 3 was performed through a Mannich-type condensation between 2-cyano-5-hydroxy-3-methylnaphtho[1,2]furan 2a, 1.5 eq of a primary amine and 3 eq of formaldehyde. Similarly, 2-cyano-5-hydroxy-3-methylfuro[2,3-f]quinoline 2b gave the dihydro furo[1,3]oxazino-quinoline compounds 4. Heating a mixture of the naphthofuran 2a, tert-butylamine and formaldehyde at toluene reflux led to the furonaphthoxazine 3e, which decomposes to afford an o-quinonemethide intermediate 5. The latter was trapped with 1-morpholinopropene to give a dihydro furonaphthopyran derivative 6. All compounds 2, 3, 4 and 6 were assayed for in vitro cytotoxic activity toward L 1210, MDA-MB 231 and PC tumor cells. Among them, furonaphth[1,3]oxazines 3b, 3c, and furo[1,3]oxazinoquinolines 4c, 4d showed significant activity against L 1210 cells, while furoquinoline 2b was the most cytotoxic compound towards all three cell lines.
