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Pregled bibliografske jedinice broj: 146386

Časopis

Autori: Raić-Malić, Silvana; Tomašković, Linda; Mrvoš-Sermek, Draginja; Prugovečki, Biserka; Cetina, Mario; Grdiša, Mira; Pavelić, Krešimir; Mannschreck, Albrecht; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen
Naslov: Spirobipyridopyrans, Spirobinaphthopyrans, Indolinospiropyridopyrans, Indolinospironaphthopyrans and Indolinospironaphtho-1, 4-oxazines: Synthesis, Study of X-Ray Crystal Structure and Biological, Antitumoral and Antiviral Evaluation
Izvornik: Bioorganic & Medicinal Chemistry (0968-0896) 12 (2004), 5; 1037-1045
Vrsta rada: članak
Ključne riječi: spiropyrans; 1H and 13C NMR spectra; single crystal X-ray analysis; cytostatic activities; antiviral activities
Sažetak:
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 the 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 positioned almost perpendicularly to each other. The five-membered 2, 3-dihydropyrrolo moiety of the indoline ring adopts an envelope conformation in both structures. Of all the compounds of this series, indolinospirobenzopyran (9), containing a methoxy group at the position 6 of the benzopyran ring, exhibited the most pronounced inhibitory effects on the growth of human CEM (IC50: 0.68 mg/ml) and Molt4/C8 (IC50: 0.71 mg/ml) cells. Spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) (IC50: 0.9 mM) cells but not the growth of normal fibroblasts (WI38). The best cytostatic activity was achieved with the compounds 8, 9 and 10, from the class of indolinospirobenzopyrans. The indolinospirobenzopyrans 4, 6-8, 10 and the indolinospironaphtho-1, 4-oxazine 16 showed, albeit modest, selectivity as antiviral agents against varicella-zoster virus (VZV) and/or cytomegalovirus (CMV) (EC50 within the concentration range of 0.4-4 µ ; ; ; g/ml).
Projekt / tema: 0098093, 0125003, 0119632
Izvorni jezik: ENG
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bazama podataka:
Current Contents Connect (CCC)
MEDLINE
Scopus
SCI-EXP, SSCI i/ili A&HCI
Science Citation Index Expanded (SCI-EXP) (sastavni dio Web of Science Core Collectiona)
Kategorija: Znanstveni
Znanstvena područja:
Kemija
URL cjelovitog teksta:
Google Scholar: Spirobipyridopyrans, Spirobinaphthopyrans, Indolinospiropyridopyrans, Indolinospironaphthopyrans and Indolinospironaphtho-1, 4-oxazines: Synthesis, Study of X-Ray Crystal Structure and Biological, Antitumoral and Antiviral Evaluation



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