Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases

The tri-component synthesis of novel chiral benzimidazole Mannich bases, by reaction between benzimidazole, aqueous 30% formaldehyde and an amine, the biological evaluation and DFT studies of the new compounds are reported here. The 1 H-NMR, 13 C-NMR, FTIR spectra and elemental analysis confirm the...

Full description

Saved in:
Bibliographic Details
Published in:BMC chemistry 2020-07, Vol.14 (1), p.45-45, Article 45
Main Authors: Marinescu, Maria, Cinteză, Ludmila Otilia, Marton, George Iuliu, Chifiriuc, Mariana-Carmen, Popa, Marcela, Stănculescu, Ioana, Zălaru, Christina-Marie, Stavarache, Cristina-Elena
Format: Article
Language:English
Subjects:
Antimicrobial activity
Antimicrobial agents
Benzimidazole
Biofilm
Biological activity
Chemical analysis
Chemical bonds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Density functional theory
DFT study
In vitro methods and tests
Mannich base
Molecular orbitals
Morpholine
NMR
Nuclear magnetic resonance
Organic Chemistry
Research Article
Synthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The tri-component synthesis of novel chiral benzimidazole Mannich bases, by reaction between benzimidazole, aqueous 30% formaldehyde and an amine, the biological evaluation and DFT studies of the new compounds are reported here. The 1 H-NMR, 13 C-NMR, FTIR spectra and elemental analysis confirm the structures of the new compounds. All synthesized compounds were screened by qualitative and quantitative methods for their in vitro antibacterial activity against 4 bacterial strains. DFT studies were accomplished using GAMESS 2012 software and HOMO–LUMO analysis allowed the calculation of electronic and structural parameters of the chiral Mannich bases. The geometry of 1-methylpiperazine, the cumulated Mullikan atomic charges of the two heteroatoms and of the methyl, and the value of the global electrophilicity index (ω = 0.0527) of the M-1 molecule is correlated with its good antimicrobial activity. It was found that the presence of saturated heterocycles from the amine molecule, 1-methyl piperazine and morpholine, respectively, contributes to an increased biological activity, compared to aromatic amino analogs, diphenylamino-, 4-nitroamino- and 4-aminobenzoic acid. The planarity of the molecules, specific bond lengths and localization of HOMO–LUMO orbitals is responsible for the best biological activities of the compounds.
ISSN:2661-801X
2661-801X
DOI:10.1186/s13065-020-00697-z