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Novel Derivatives of Benzo[b]thieno[2,3-c]quinolones:  Synthesis, Photochemical Synthesis, and Antitumor Evaluation (CROSBI ID 100770)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Dogan Koružnjak, Jasna ; Grdiša, Mira ; Slade, Neda ; Zamola, Branimir ; Pavelić, Krešimir ; Karminski-Zamola, Grace Novel Derivatives of Benzo[b]thieno[2,3-c]quinolones:  Synthesis, Photochemical Synthesis, and Antitumor Evaluation // Journal of medicinal chemistry, 46 (2003), 21; 4516-4524. doi: 10.1021/jm0210966

Podaci o odgovornosti

Dogan Koružnjak, Jasna ; Grdiša, Mira ; Slade, Neda ; Zamola, Branimir ; Pavelić, Krešimir ; Karminski-Zamola, Grace

engleski

Novel Derivatives of Benzo[b]thieno[2,3-c]quinolones:  Synthesis, Photochemical Synthesis, and Antitumor Evaluation

Novel derivatives of benzo(b)thieno(2, 3-c)quinolones 3a-j were synthesized in a multistep synthesis starting from substituted benzo(b)thiophene-2-carbonyl chlorides, to their corresponding benzo(b)thiophene-2-carboxamides, which were photochemically dehydrohalogenated to their corresponding substituted benzo(b)thieno(2, 3-c)quinolones. Compound 4 was prepared from 3i by alkylation with 3-dimethylaminopropyl chloride in the presence of NaH. Compounds 7a, b were prepared from 3g in the multistep synthesis from compounds 5 and 6. Compounds 3b, 3c-f, 3h, 7a, and 7b were found to exert cytostatic activity against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cervical carcinoma (HeLa), laryngeal carcinoma (Hep2), colon carcinoma (CaCo-2), melanoma (HBL), human fibroblast cell lines (WI-38). The compounds that bear a 3-dimethylaminopropyl substituent on the quinolone nitrogen (3b, 3c-f, 3h) showed higher antitumor activity than compounds bearing the same substituent on the amidic nitrogen (7a and 7b). The compound 3h, which has a 3-dimethylaminopropyl substituent on the quinolone nitrogen and a methoxycarbonyl substituent at position 9, had marked antitumor activity. Because of strong cytotoxic effect of compound 4 on melanoma cells (HBL, ME 67.3 and ME 67.1) a potential mechanism of action was examined. Analysis of DNA and Annexin-V-FLUOS staining indicated that compound 4 causes cell death by apoptosis.

derivatives of benzo((b)thieno(2, 3-c)quinolones ; antitumor effect ; synthesis

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Podaci o izdanju

46 (21)

2003.

4516-4524

objavljeno

0022-2623

1520-4804

10.1021/jm0210966

Povezanost rada

Kemija, Temeljne medicinske znanosti

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