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 remarkable selectivity towards breast cancer cell line MCF-7. The most distinct and selective antiviral activity towards Coxackieviruses 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.

Synthesis and SAR Study of Novel Amidino 2-substituted Benzimidazoles as Potential Antibacterial Agents

“…[19,20] The positively charged amidine groups are attracted by electrostatic interactions to negatively charged DNA thus enabling selective binding. [21] In view of the afore-mentioned findings and in a continuation of our research on biologically active heterocycles, [22][23][24][25] we hereby describe the synthesis of a new 2,5(6)-disubstituted benzimidazole derivatives and their evaluation as antibacterial agents. The structure activity relationship of their antibacterial activities was also examinate.…”

Novel biologically active nitro and amino substituted benzimidazo[1,2-a]quinolines

“…The growth inhibition activity was assessed as described previously [ 7,8,15,16,20 ]. The panel cell lines were inoculated onto a series of standard 96-well microtiter plates on day 0, at 1×10 4 to 3×10 4 cells/mL, depending on the doubling times of a specific cell line.…”

“…2,3,4 The benzimidazole unit which has a structural similarity with purine, is also the key building block for a variety of derivatives that are known to play crucial roles in the functions of a number of biologically important molecules. Besides, benzimidazoles represent the major backbone of numerous of synthetic medical and biochemical agents possessing different chemical and pharmacological features which impart them diverse biological properties like anticancer, 5,6,7 antiviral, 8,9 antibacterial, 10,11 antifungal, 12 antihistaminic 13 and anticonvulsant activity. 14 As a part of our continuing search for potential anticancer agents related to benzimidazole derivatives, we have recently reported on the synthesis, cytostatic evaluation, DNA/RNA interaction study and proteomic profiling of a series of amidino-substituted heterocyclic benzimidazoles and benzimidazo [1,2-a]quinolines.…”

A novel approach to synthesis of flibanserin

“…A variety of benzimidazoles are in used, like Thiabendazole, Flubendazole (antihelminthic), Omeprazole, Lansoprazole (anti-ulcerative) and Astemizole (anti-histaminic). The chemistry and pharmacology of benzimidazoles have been of great interest to medicinal chemistry [7,8] , because of its derivatives possessed various biological activities such as anti-oxidant [9,10], anti-microbial [11][12][13][14][15][16] , antihelmentic [17][18][19], anti-cancer [20], anti-hypertensive [21], anti-neoplastic [22], anti-inflammatory [23,24], analgesic [25], anti-protozoal [26,27], anti hepatitis activities [28] and also shows anti-depressant activity [29].…”