69570-99-6Relevant articles and documents
Design, synthesis, mechanistic studies and in silico ADME predictions of benzimidazole derivatives as novel antifungal agents
Abdel-Aziz, Mohamed,Abdel-Rahman, Hamdy M.,Abdelhafez, El Shimaa M. N.,Abou El-Ella, Dalal A.,Ibrahem, Reham A.,Morcoss, Martha M.
, (2020)
Herein, novel three series of benzimidazole scaffold bearing hydrazone, 1,2,4-triazole and 1,3,4-oxadiazole moieties 1-3, 4a-j, 6a-c and 7 derivatives were designed, synthesized and evaluated for their antimicrobial activity. The structures of the prepared compounds were assigned using different spectroscopic techniques such as IR, 1H NMR, 13C NMR and elemental analyses. Compounds 3, 4a, 4e and 4f exhibited remarkable antifungal activity against C. albicans and C. neoformans var. grubii with MIC values ranging from 4 to 16 μg/mL. Furthermore, they were not cytotoxic against red blood cells and human embryonic kidney cells at concentration up to 32 μg/mL. The study was expanded to forecast the mechanism of action of the prepared compounds and determine sterol quantitation method (SQM) by spectrophotometric assay. On the other hand, compound 4e showed the highest inhibitory activity against lanosterol 14α-demethylase (CYP51) with IC50 value = 0.19 μg/mL compared to fluconazole as reference IC50 value = 0.62 μg/mL. Also, compounds 4d and 4f exhibited mild to moderate antibacterial activity. Moreover, molecular docking of the active target compound 4e in active site of lanosterol 14α-demethylase (CYP51) revealed that docking scores and binding mode are comparable to that of co-crystallized ligand confirming their antifungal activity. In silico ADME prediction investigations also forecasting the drug-like characters of these compounds.
Novel clarithromycin analogs with C-4′′ 2-arylbenzimidazolyl bishydrazide side chain: Synthesis and antibacterial evaluation
Qi, Yunkun,Ma, Ruixin,Li, Xin,Hu, Yue,Ma, Siti,Cong, Chao,Ma, Xiaodong,Cui, Wenping,Ma, Shutao
experimental part, p. 966 - 971 (2012/07/01)
A series of novel 4′′-O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4′′-O-2- arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4′′ bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.
Very fast and efficient synthesis of some novel substituted 2-arylbenzimidazoles in water using ZrOCl2?nH2O on montmorillonite K10 as catalyst
Rostamizadeh, Shahnaz,Amani, Ali Mohammad,Aryan, Reza,Ghaieni, Hamid Reza,Norouzi, Leila
experimental part, p. 547 - 552 (2010/06/16)
A simple and eco-friendly protocol for the synthesis of some novel substituted 2-arylbenzimidazoles was developed. In this process, these compounds were prepared in water as the solvent using ZrOCl2?nH 2O supported on montmorillonite K10 as an efficient water tolerating Lewis acid. The reaction was performed under mild conditions with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct.
