In this study, a series of phenyl, furyl and 1H-1,2,4-triazole substituted benzyl and alkyl ethers were synthesized, characterized by all spectral analysis, and evaluated for their antibacterial and antifungal activities against Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, Candida albicans and Candida krusei. From phenyl substituted series, compound 1-(2-(3,4-dichlorobenzyloxy)-2phenylethyl)-1H-1,2,4-triazole (7 i) exhibited the most potent antibacterial activity with lowest MIC value of 6.25 μg/mL against MRSA and from furyl substituted series, most of the compounds exhibited the most potent antifungal activity with lowest MIC value of 6.25 μg/mL against Candida Krusei. Furthermore, the absorption, distribution, metabolism, and excretion (ADME) and drug-likeness characteristic of the compounds were calculated, and it was observed that all compounds met majority the criteria of five different drug filters. Finally, docking simulations revealed that some compounds showed high affinity to an CYP51 antifungal target structure (PDB: 3L4D).
The asymmetric unit of the title compound, C21H17Cl2N3O, contains two crystallographically independent molecules with similar conformations. The benzotriazole ring is oriented at dihedral angles of 30.61 (5) and 43.36 (5)°, respectively, to the phenyl and dichlorophenyl rings in one molecule, and 32.25 (5) and 41.04 (5)° in the other. The dihedral angles between the phenyl and dichlorophenyl rings are 66.38 (7) and 66.14 (6)° in the two molecules. An intramolecular O—H⋯N hydrogen bond links the benzotriazole ring and phenylpropanol unit in each molecule. In the crystal, weak intermolecular C—H⋯N hydrogen bonds link the molecules into chains along the a axis. π–π stacking between the dichlorophenyl rings [centroid–centroid distances = 3.809 (1) and 3.735 (1) Å] may further stabilize the crystal structure.
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