Synthesis, crystal structure and antiproliferative evaluation of some new substituted benzothiazoles and styrylbenzothiazoles.
The multistep synthesis of a series of new substituted-benzothiazoles as hydrochloride or quaternary salts is described. 6-Amidino substituted 2-aminobenzothiazoles (5, 6), N-methyl-2-(4-cyanostyryl)benzothiazolium iodide (8), cyano-substituted-2-styrylbenzothiazoles (9-11) and amidino and bis-amidino-substituted 2-styrylbenzothiazoles (12-17) were prepared. The crystal structure of amidino derivative (6) was determined by single crystal X-ray analysis. All new prepared compounds were tested on the cytostatic activities against malignant cell lines: (SW620, colon carcinoma; Hep2, laryngeal carcinoma; HBL, melanoma; HeLa, cervical carcinoma and WI38, human normal fibroblasts). The compounds exerted a different inhibitory effect, depended on concentration and type of the cells. The best inhibitory effect was achieved with compounds (12-15), with slight differences among them. All of them inhibited the growth of examined tumor cell lines and also normal fibroblasts. Other examined compounds exhibited a moderate inhibitory effect, depending on type of the cells. Majority of them inhibited the growth of HeLa cells and WI38.
Caleta
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I
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, P. O. Box 177, HR-10000 Zagreb, Croatia.
Grdisa
M
M
Mrvos-Sermek
D
D
Cetina
M
M
Tralić-Kulenović
V
V
Pavelić
K
K
Karminski-Zamola
G
G
D052160:Benzothiazoles; D002455:Cell Division / Q000187:drug effects / Q000502:physiology; D002460:Cell Line; D045744:Cell Line, Tumor; D003460:Crystallization; D018360:Crystallography, X-Ray / Q000379:methods; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical / Q000379:methods; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D006131:Growth Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006367:HeLa Cells; D006801:Humans; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D052160:Benzothiazoles; D006131:Growth Inhibitors; D013844:Thiazoles; C005465:benzothiazole