Raic-Malic, Silvana and Tomaskovic, Linda and Mrvos-Sermek, Draginja and Prugovecki, Biserka and Cetina, Mario and Grdisa, Mira and Pavelic, Krešimir and Mannschreck, Albrecht and Balzarini, Jan and De Clercq, Erik and Mintas, Mladen (2004) Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation. BIOORGANIC & MEDICINAL CHEMISTRY, 12 (5). pp. 1037-1045. ISSN 0968-0896, 1464-3391
Full text not available from this repository. (Request a copy)Abstract
The novel racemic indolinospiroberizopyrans (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 stereo structures 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, spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) (IC50: 0.9 muM) cells but not the growth of normal fibroblasts (WI38). Indolinospirobenzopyrans (8-10) showed significant cytostatic activities against all tumor cell lines. However, these compounds also exhibited a cytotoxic effect on normal human fibroblasts. 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 1.0-12.6 muM). (C) 2003 Elsevier Ltd. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOCHROMISM; spiropyrans; H-1 and C-13 NMR spectra; single crystal X-ray analysis; cytostatic activities; antiviral activities |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Prof.Dr. Mannschreck |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 22 Jul 2021 09:59 |
| Last Modified: | 22 Jul 2021 09:59 |
| URI: | https://pred.uni-regensburg.de/id/eprint/37899 |
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