A novel series of hydroxy and non-hydroxy long chain substituted 1,3,4-oxadiazole moiety bearing 2-methyl-1H-benzimidazoles 15(a-d) have been synthesized from cyclization reaction of 2-(2-methyl-1H-benzimidazol-1-yl) acetohydrazide (13) with different unsaturated hydroxy and non-hydroxy fatty esters in the presence of phosphorus oxychloride and product obtained in appreciable yield. Compound (13) was synthesized from the corresponding ethyl (2-methyl-1H-benzimidazol-1-yl) acetate (12) and 2-methyl-1H-benzimidazole (11). All the synthesized compounds were characterized with the help of IR, 1 H NMR, 13 C NMR, and mass spectral studies. These compounds were tested for cytotoxic (or antiproliferative) activity against normal human blood cells (PBMCs), Hep3B (human hepatocellular carcinoma), MCF 7 (human breast adenocarcinoma), and HeLa (human cervical carcinoma) cell lines.
In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, H NMR,C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8'R)-8' hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2'R)(2'-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8'R)-8'-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
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