Hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives and evaluation of their anticancer and antimycobacterial activity

Abstract

The design, synthesis, structure, and in vitro anticancer and antimycobacterial activity of new hybrid imidazole (benzimidazole)/pyridine (quinoline) derivatives are described. The strategy adopted for synthesis is straight and efficient, involving a three-step setup procedure: N-acylation, N-alkylation, and quaternization of nitrogen heterocycle. The solubility in microbiological medium and anticancer and antimycobacterial activity of a selection of new synthesized compounds were evaluated. The hybrid derivatives have an excellent solubility in microbiological medium, which make them promising from the pharmacological properties point of view. One of the hybrid compounds, 9 (with a benzimidazole and 8-aminoquinoline skeleton), exhibits a very good and selective antitumor activity against Renal Cancer A498 and Breast Cancer MDA-MB-468. Moreover, the anticancer assay suggests that the hybrid Imz (Bimz)/2-AP (8-AQ) compounds present a specific affinity to Renal Cancer A498. Concerning the antimycobacterial activity, only the hybrid compound, 9, has a significant activity. SAR correlations have been performed.

Microwave Assisted Reactions of Azaheterocycles Formedicinal Chemistry Applications

“…Five membered ring azaheterocycles, especially pyrroles, pyrazoles, imidazoles, triazoles, tetrazoles and their fused derivatives, are multitarget pharmacophores with a large variety of biological activities such as antibacterial, antifungal, antitubercular, antihelmintic, antiplasmodial, anticancer, anti-inflammatory, cardiotonic, antihypertensive, antithrombotic, antihistaminic, antiulcer, analgesic, neuroleptic, etc. [16][17][18][19][20][21][22][23][24]. Having these considerations in view, a lot of attention was paid by researchers for obtaining new compounds with such skeleton, using both conventional TH and MW technology.…”

“…Compounds containing pyridine, pyridazine, pyrimidine, pyrazine, -and their fused derivatives-, are described to possess a wide range of biological activities, with these including antiviral, anti-HIV, antituberculosis, antimalarial, antileishmanial, antibacterial, antifungal, anti-inflammatory, anticancer, antihypertensive, diuretics, antiaggregative, antiplatelet, cardiotonics, antineurodegenerative, antidepressant, anxiolytics, anticonvulsivant, analgesic, sedatives, antiallergic, etc. [16,21,[40][41][42][43][44][45][46][47][48][49][50][51][52][53]. A large variety of syntheses are described for these compounds, with some of them using MW technology.…”

Synthesis and antitumor activity of new isolated and fused heterobicyclic nitrogen systems containing 1,3,4-thiadiazole moiety derived from N1,N2-diaryl hydrazine compound

“…The design and synthesis of heterocyclic molecules from different small groups of heterocycles with influence on biological, pharmaceutical and therapeutic area, have been reported to control the high resistance of microbes towards the used antibiotics [1][2][3][4][5]. Cancer chemotherapy is complex, expensive and often rather inefficient because of toxicity levels and non-specificity of drugs and the emergence of drug resistance and multi-drug-resistant (MDR) strains [6][7][8]. A lot ofheterocyclic nitrogen systems have exhibitednoticeableantitumor activity especially 1,2,4-triazine derivatives as cyclin-dependent kinase (CDK2) inhibitors for the tumor cells (DNA damage repair) [9][10].…”

Pyridine-Imidazlolium Salts: Oxidatively Cleavage of N-C Bond via Nitration

“…In the past decades five and six member ring azaheterocycles compounds, especially imidazole and (di)azine, became invaluable scaffolds in drug designing because of their large variety of biological activities, such as anticancer, antimicrobial (antibacterial, antifungal, antitubercular), antimalarial, anti-inflammatory, antidepressant, analgesic, antihypertensive etc. [1][2][3][4][5][6][7].…”