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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 th...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7382033/ https://www.ncbi.nlm.nih.gov/pubmed/32724899 http://dx.doi.org/10.1186/s13065-020-00697-z |
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author | Marinescu, Maria Cinteză, Ludmila Otilia Marton, George Iuliu Chifiriuc, Mariana-Carmen Popa, Marcela Stănculescu, Ioana Zălaru, Christina-Marie Stavarache, Cristina-Elena |
author_facet | Marinescu, Maria Cinteză, Ludmila Otilia Marton, George Iuliu Chifiriuc, Mariana-Carmen Popa, Marcela Stănculescu, Ioana Zălaru, Christina-Marie Stavarache, Cristina-Elena |
author_sort | Marinescu, Maria |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-7382033 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-73820332020-07-27 Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases Marinescu, Maria Cinteză, Ludmila Otilia Marton, George Iuliu Chifiriuc, Mariana-Carmen Popa, Marcela Stănculescu, Ioana Zălaru, Christina-Marie Stavarache, Cristina-Elena BMC Chem Research Article 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. Springer International Publishing 2020-07-25 /pmc/articles/PMC7382033/ /pubmed/32724899 http://dx.doi.org/10.1186/s13065-020-00697-z Text en © The Author(s) 2020 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated in a credit line to the data. |
spellingShingle | Research Article Marinescu, Maria Cinteză, Ludmila Otilia Marton, George Iuliu Chifiriuc, Mariana-Carmen Popa, Marcela Stănculescu, Ioana Zălaru, Christina-Marie Stavarache, Cristina-Elena Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases |
title | Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases |
title_full | Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases |
title_fullStr | Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases |
title_full_unstemmed | Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases |
title_short | Synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole Mannich bases |
title_sort | synthesis, density functional theory study and in vitro antimicrobial evaluation of new benzimidazole mannich bases |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7382033/ https://www.ncbi.nlm.nih.gov/pubmed/32724899 http://dx.doi.org/10.1186/s13065-020-00697-z |
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