title: 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.
authors.affiliation: a Faculty of Chemistry , "Alexandru Ioan Cuza" University of Iasi , Iasi , Romania.
authors.forename: Dorina
authors.initials: D
authors.lastname: Mantu
authors.affiliation: a Faculty of Chemistry , "Alexandru Ioan Cuza" University of Iasi , Iasi , Romania.
authors.forename: Vasilichia
authors.initials: V
authors.lastname: Antoci
authors.affiliation: a Faculty of Chemistry , "Alexandru Ioan Cuza" University of Iasi , Iasi , Romania.
authors.forename: Costel
authors.initials: C
authors.lastname: Moldoveanu
authors.affiliation: a Faculty of Chemistry , "Alexandru Ioan Cuza" University of Iasi , Iasi , Romania.
authors.forename: Gheorghita
authors.initials: G
authors.lastname: Zbancioc
authors.affiliation: a Faculty of Chemistry , "Alexandru Ioan Cuza" University of Iasi , Iasi , Romania.
authors.forename: Ionel I
authors.initials: II
authors.lastname: Mangalagiu
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012995:Solubility; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D001562:Benzimidazoles; D011804:Quinolines; C031000:benzimidazole; C037219:quinoline
keywords: Anticancer; antimycobacterial; hybrid imidazole (benzimidazole)/pyridine (quinoline); synthesis