ABSTRACT
A number of 5-oxo-1-phenyl-4-(substituted methyl) pyrrolidine-3-carboxylic acid derivatives bearing pyrrolidine ring and methylamino residues in their structure were synthesized as potential antibacterial drugs. The chemical structures of all the compounds were established by their UV-Vis absorption spectroscopy, IR, 1H, 13C NMR and mass spectroscopy. The in vitro antibacterial screening of all novel compounds was done against gram-positive Staphylococcus aureus, Bacillus subtilis and gram-negative Pseudomonas aeruginosa. The results revealed that compounds 5d, e, f and g showed moderate to good activity against the tested microbes.
Subject(s)
Anti-Bacterial Agents/pharmacology , Carboxylic Acids/chemistry , Pyrrolidines/chemistry , Anti-Bacterial Agents/chemistry , Bacillus subtilis/drug effects , Mass Spectrometry , Microbial Sensitivity Tests , Molecular Structure , Proton Magnetic Resonance Spectroscopy , Pseudomonas aeruginosa/drug effects , Staphylococcus aureus/drug effects , Structure-Activity RelationshipABSTRACT
The synthesized compound (2Z,4Z)-2,4-bis(4-chlorobenzylidene)-5-oxo-1-phenylpyrrolidine-3-carboxylic acid (BCOPCA) was characterised by Ultraviolet, FT-Infra Red, 1H, 13C Nuclear Magnetic Resonance and mass spectroscopy. The compound was further subjected to quantum chemical calculations at the level of density functional theory (DFT) using 6-31G (d,p) basis sets method with B3LYP and CAM-B3LYP hybrid functionals. The intramolecular interactions, polarizability, hyperpolarizability and nonlinear optical properties of the title compound were also incorporated in the study. The total first static hyperpolarizability (ß0 = 19.477 × 10-30 and 16.924 × 10-30 esu) value was also computed and indicated the title molecule as an interesting forthcoming NLO material. The other thermodynamic properties (entropy, heat capacity and zero vibrational energy) were also discussed. The study also includes NBO computations, complete vibrational assignments, Mulliken charges, UV-Visible spectral analysis and HOMO-LUMO energies. The regions of low and high electron density were obtained from MESP and ESP maps. The calculated parameters for BCOPCA using aforementioned functions are harmonious with the experimental findings. The in-vitro antimicrobial activity and molecular docking studies of BCOPCA were also done and showed a good correlation.
