Pyran derivatives. XX. 2-Aminochromone benzo-fused derivatives with antiproliferative properties
Roma, G.; Di Braccio, M.; Grossi, G.; Marzano, C.; Simonato, M.; Bordin, F.
Farmaco 53(7): 494-503
1998
ISSN/ISBN: 0014-827X PMID: 9836462 Document Number: 494595
The N-substituted 2-aminochromones 1 and their benzo-fused derivatives 24 described herein were mostly prepared by treating the corresponding (methylthio) derivatives 10-13 with an excess of the proper amines. Only the morpholino derivatives 3d and 4c were obtained from the reaction of the ethyl 3-morpholino-3-oxopropanoate/POCl3 reagent with 1-naphthol or 1-methyl-2-naphthol, respectively. The amino derivatives 14, as well as their methylthio analogues 10-13, were tested in vitro for their inhibitory activity on the infectivity of T2 bacteriophage, on the macromolecular synthesis in Ehrlich cells and on the clonal growth capacity of HeLa cells. Several of the angular or linear aminonaphthopyranones 2 and 3 or 4, respectively, and the (methylthio) derivatives 10, 11 and 13 induced a significant inhibition of DNA synthesis, but usually a clearly lower inhibition of clonal growth. Only the linear 2-amino- 10-methyl-4H-naphtho (2,3-b) pyran-4-ones 4a and 4b significantly inhibited the clonal growth in HeLa cells and T2 bacteriophage infectivity, respectively.