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


ABSTRACT: 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 1H-NMR, 13C-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 (??=?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.

SUBMITTER: Marinescu M 

PROVIDER: S-EPMC7382033 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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

Marinescu Maria M   Cinteză Ludmila Otilia LO   Marton George Iuliu GI   Chifiriuc Mariana-Carmen MC   Popa Marcela M   Stănculescu Ioana I   Zălaru Christina-Marie CM   Stavarache Cristina-Elena CE  

BMC chemistry 20200725 1


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 <sup>1</sup>H-NMR, <sup>13</sup>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 strai  ...[more]

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