Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles.
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.
Starcević
Kristina
K
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, PO Box 177, HR-10000 Zagreb, Croatia.
Kralj
Marijeta
M
Ester
Katja
K
Sabol
Ivan
I
Grce
Magdalena
M
Pavelić
Kresimir
K
Karminski-Zamola
Grace
G
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
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D001562:Benzimidazoles