title: Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles.
abstract: We have prepared a set of heterocyclic benzimidazole derivatives bearing amidino substituents at C-5 of benzimidazole ring, by introducing various heterocyclic nuclei (pyridine, N-methyl-pyrrole or imidazole) at C-2, and evaluated their antitumor and antiviral activities. The most pronounced antiproliferative activity was shown with compounds 6 and 9, having imidazolinylamidino-substituent. Interestingly, all compounds show noticeable selectivity toward breast cancer cell line MCF-7. The most distinct and selective antiviral activity toward coxsackieviruses and echoviruses was observed with compounds having pyridine ring at C-2. Especially interesting was fairly strong activity of 4 and 8 toward adenoviruses, which could be considered as leads against adenoviral replication.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, PO Box 177, HR-10000 Zagreb, Croatia.
authors.forename: Kristina
authors.initials: K
authors.lastname: Starcević
authors.forename: Marijeta
authors.initials: M
authors.lastname: Kralj
authors.forename: Katja
authors.initials: K
authors.lastname: Ester
authors.forename: Ivan
authors.initials: I
authors.lastname: Sabol
authors.forename: Magdalena
authors.initials: M
authors.lastname: Grce
authors.forename: Kresimir
authors.initials: K
authors.lastname: Pavelić
authors.forename: Grace
authors.initials: G
authors.lastname: Karminski-Zamola
mesh_terms: D000256:Adenoviridae / Q000187:drug effects; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004770:Enterovirus / Q000187:drug effects; D005347:Fibroblasts; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000998:Antiviral Agents; D001562:Benzimidazoles