Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide

Abstract

In the present study, N-(thiophen-2-ylmethyl)thiophene-2-carboxamide, C10H9NOS2, (I), was obtained by the reaction of thiophene-2-carbonyl chloride and thiophen-2-ylmethanamine. Characterization of (I) was carried out using X-ray diffraction, spectroscopic techniques and elemental analyses. The DFT/B3LYP/6-311++G(d,p) theoretical level was successfully applied to calculate the optimized geometry and the local and global chemical activity parameters. The results obtained show good agreement between the experimental and theoretical geometrical parameters. The local and global chemical activity parameters were examined to determine the electrophilic and nucleophilic sites in (I). The natural bond orbital (NBO) analysis of (I) gives an efficient methodology for investigating the inter- and intramolecular bonding, as well as giving a convenient basis for investigating charge transfer or conjugative interactions in molecular systems. Also, the antimicrobial activity of (I) was investigated against eight microorganisms using the microdilution method and it is found to have an effective antibacterial activity. In addition, molecular docking studies were calculated in order to understand the nature of the binding of (I) with a lung cancer protein (PDB entry 1x2j).

New Insights on Glutathione’s Supramolecular Arrangement and Its In Silico Analysis as an Angiotensin-Converting Enzyme Inhibitor

“…The red convex area above the glutamic acid correlates with the hydrogen bond interactions N 1 -H The fingerprint plots (Figure 10) allow us to analyze the differences in the intermolecular patterns of the contacts and quantitatively evaluate the contributions among atoms [41]. The contacts involving H• • • O accumulated a percentage of 50% and are viewed as a distinct pair of spikes, evidence that the H-bonds are dominant in the crystalline environment [42]. The H• • • H contacts, close to 34%, with a decrease of 0.8% for GSHB, contribute to the overall crystal packing.…”

Synthesis, DFT investigations, antioxidant, antibacterial activity and SAR-study of novel thiophene-2-carboxamide derivatives

“…Additionally, thiophene-2-carboxamide was considered to be a lead compound for drug discovery [ 31 , 32 ]; for example; nitro thiophene-2-carboxamide 4 was used as a narrow spectrum antibacterial lead compound [ 33 ] and thiophene-2-carboxamide 5 was used as IKK-2 potent lead inhibitor [ 34 ]. Previous DFT-study for thiophene-2-carboxamide derivatives showed that N -(thiophen-2-ylmethyl)thiophene-2-carboxamide displays close experimental and theoretical structure parameters with (ΔE H-L ) 5.031 eV [ 35 ]. While thiophene-thiadiazole hybrid derivatives (FMOs) shows close values between 3.83 and 4.18 eV [ 36 ].…”