Naslov
Novel substituted derivatives of amidino-benzo[b]thieno[2, 3-c]quinolones: synthesis and antitumor evaluation

Autori
Jarak, Ivana ; Frković, Danijel ; Šuman, Lidija ; Kralj, Marijeta ; Pavelić, Krešimir ; Karminski-Zamola, Grace

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, ostalo

Izvornik
XVIII International Symposium on Medicinal Chemistry / Prous, J.R. - Kopenhagen : Prous Science, 2004, 390-390

Skup
XVIII International Symposium on Medicinal Chemistry

Mjesto i datum
Kopenhagen, Danska, 15.08.2004. - 19.08.2004

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
quinolone; amidine; antitumor

Sažetak
Novel substituted derivatives of amidino-benzo[b]thieno[2, 3-c] quinolones: synthesis and antitumor evaluation Ivana Jarak1, Danijela Frković2, Lidija Šuman2, Marijeta Kralj2, Krešimir Pavelić2 and Grace Karminski-Zamola 1Department of Organic Chemistry, Faculty of Chemical Eng. and Technology, University of Zagreb, Marulićev trg 20, 10000 Zagreb, Croatia, 2Department of Moleculare Medicine "Rudjer Bošković" Institute, Bijenička cesta 54, 10002 Zagreb, Croatia Novel substituted derivatives of amidino-benzo[b]thieno[2, 3-c]quinolones as hydrochloride salts, were synthesized in multistep synthesis. Starting from substituted cinnamic acids, in the reaction with thionyl chloride, were prepared corresponding benzo[b]thieno carbonyl chlorides which reacted with 4-amino-benzonitrile, or 4-substituted aminobenzenes to give the corresponding anilides. Obtained anilides were photochemically cyclized into corresponding benzo[b]thieno[2, 3c] quinolones. Application of Pinner reaction afforded the amidino compounds. Antitumor evaluation were carried out on 6 human cell lines, 5 of which were derived from 5 cancer types and one normal, fibroblast cell line. The following cell lines were used: HeLa (cervical carcinoma), MCF-7 (breast carcinoma), SW 620 (colon carcinoma), MiaPaCa-2 (pancreatic carcinoma), Hep-2 (laryngeal carcinoma) and WI 38 (diploid fibroblasts). The cell growth rate was evaluated by performing the MTT assay. All compounds showed certain antiproliferative effect on these cell lines. However, compounds from the group I manifested markedly differential growth inhibition and/or cytotoxicity and selectivity towards tumor cells, while in the group II only methoxycarbonyl substituted compound showed differential growth inhibition. [1] Dogan Koružnjak J. Grdiša M. Slade N. Zamola B. Pavelić K. Karminski-Zamola G. Novel derivatives of benzo[b]thieno[2, 3-c]quinolones: Synthesis Photochemical synthesis and Antitumor Evaluation. J Med Chem 2003 ; 46:4516-4524. [2] Dogan Koružnjak J. Slade N. Zamola B. Pavelić K. Karminski-Zamola G. Synthesis, Photochemical synthesis and Antitumor Evaluation of Novel derivatives of Thieno[3', 2' :4, 5]thieno[2, 3-c]quinolones. Chem Pharm Bull 2002 ; 50: 656-660. [3] Tanious F. Wilson WD. Wang L. Kumar A. Boykin DW. Marty C. Baldeyrou B. Bailly C. Cooperative dimerization of a heterocyclic diamidine determines sequence-specific DNA recognition. Biochemistry 2003 ; 42(46):13576-13584.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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