engleski

Spirobipyridopyrans, Spirobinaphthopyrans, Indolinospiropyridopyrans, Indolinospironaphthopyrans and Indolinospironaphtho-1, 4-oxazines: Synthesis, Study of X-Ray Crystal Structure and Antitumor Activities

The novel racemic indolinospirobenzopyrans (5- 7), indolinospironaphthopyrans (11-14) and indolinospironaphtho-1, 4-oxazine (17) were synthesized by an aldol type of condensation of 1', 3', 3' -trimethyl-2' -methyleneindoline and its 5-substituted derivatives with an appropriately substituted hydroxybenzaldehyde, hydroxynaphthaldehyde or nitrosonaphthol. An unequivocal proof of the stereostructures of 9 and 17 was obtained by their single-crystal X- ray diffraction method. A substituted indoline ring and the benzopyran ring in 9 and the naphtho-1, 4-oxazine moiety in 17 are interconnected via the common chiral atom and disposed almost perpendicularly to each other. The five-membered 2, 3-dihydropyrrolo moiety of the indoline ring adopts an envelope conformation in both structures. Among all compounds in the series, indolinospirobenzopyran (9), containing a methoxy group at the position 6 of the benzopyran ring, exhibited best inhibitory effects on the growth of human CEM (0.68 ug/ml) and Molt4/C8 (0.71 ug/ml) cell lines. Spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) cells but not the growth of normal fibroblasts (WI38).

spiropyrans ; 1H and 13C NMR spectra ; single crystal X-ray analysis ; cytostatic activities

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