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6195404 
Journal Article 
Synthesis of Furnaphth[1, 3]oxazine and Furo[1, 3]oxazinoquinoline Derivatives as Precursors for an o-Quinonemethide Structure and Potential Antitumor Agents 
Bartoli, MH; Benameur, L; Boitard, M; Bouaziz, Z; Fillion, H; Nebois, P 
1996 
Yes 
Chemical and Pharmaceutical Bulletin
ISSN: 0009-2363
EISSN: 1347-5223 
44 
3 
605 
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-b]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]oxazinoquinoline compounds 4. Heating a mixture of the naphthofuran 2a, tert-bytylamine 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 PC3 tumor cells. Among them, furonaphth[1, 3]oxazines 3b, 3c, and furo[1, 3]oxazinoquinolines 4c, 4b showed significant activity against L 1210 cells, while furoquinoline 2b was the most cytotoxic compound towards all three cell lines. 
Pharmacy And Pharmacology