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Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity
[Image: see text] 1,4-Dihydropyridines (1,4-DHPs) hold a top-notch position in the pharmaceutical world due to a broader spectrum of applications, whereas the carboxylic moiety has been an integral part of the physiological world, effective food preservatives, and antimicrobial agents. Seeking the e...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9097205/ https://www.ncbi.nlm.nih.gov/pubmed/35571772 http://dx.doi.org/10.1021/acsomega.2c01316 |
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author | Malhi, Dharambeer S. Sohal, Harvinder S. Singh, Kishanpal Almarhoon, Zainab M. Bacha, Abir Ben Al-Zaben, Maha I. |
author_facet | Malhi, Dharambeer S. Sohal, Harvinder S. Singh, Kishanpal Almarhoon, Zainab M. Bacha, Abir Ben Al-Zaben, Maha I. |
author_sort | Malhi, Dharambeer S. |
collection | PubMed |
description | [Image: see text] 1,4-Dihydropyridines (1,4-DHPs) hold a top-notch position in the pharmaceutical world due to a broader spectrum of applications, whereas the carboxylic moiety has been an integral part of the physiological world, effective food preservatives, and antimicrobial agents. Seeking the enormous potential and applications of these two classes, we worked to combine these to synthesize 2,2′-[3,5-bis(ethoxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]diacetic acid the novel dicarboxylic derivatives of 1,4-DHP (9a–k) achieved via the electro-carboxylation of tetrasubstituted-1,4-dihydropyridines (8a–k) derivatives using Mg–Pt electrodes in an undivided cell. The targeted compounds were established by (1)H, (13)C NMR, IR, and ESI-MS. Further, the synthesized compounds show excellent resistance against various microbes and the activity increased 2–3 folds after the introduction of acid groups. Compound 9b (against E. coli, S. aureus, B. subtilis, A. niger, and P. glabrum), 9d (against E. coli, K. pneumonia, S. aureus, A. janus, and F. oxysporum), 9f (against E. coli and P. fluorescens), and 9k (against F. oxysporum and P. glabrum) were found to be highly active at 4 μg/mL with reference to standard amoxicillin and fluconazole. Further, the present synthetic protocol would open new gates for other researchers to develop new molecules by bioisosteres of these substrates. |
format | Online Article Text |
id | pubmed-9097205 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-90972052022-05-13 Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity Malhi, Dharambeer S. Sohal, Harvinder S. Singh, Kishanpal Almarhoon, Zainab M. Bacha, Abir Ben Al-Zaben, Maha I. ACS Omega [Image: see text] 1,4-Dihydropyridines (1,4-DHPs) hold a top-notch position in the pharmaceutical world due to a broader spectrum of applications, whereas the carboxylic moiety has been an integral part of the physiological world, effective food preservatives, and antimicrobial agents. Seeking the enormous potential and applications of these two classes, we worked to combine these to synthesize 2,2′-[3,5-bis(ethoxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]diacetic acid the novel dicarboxylic derivatives of 1,4-DHP (9a–k) achieved via the electro-carboxylation of tetrasubstituted-1,4-dihydropyridines (8a–k) derivatives using Mg–Pt electrodes in an undivided cell. The targeted compounds were established by (1)H, (13)C NMR, IR, and ESI-MS. Further, the synthesized compounds show excellent resistance against various microbes and the activity increased 2–3 folds after the introduction of acid groups. Compound 9b (against E. coli, S. aureus, B. subtilis, A. niger, and P. glabrum), 9d (against E. coli, K. pneumonia, S. aureus, A. janus, and F. oxysporum), 9f (against E. coli and P. fluorescens), and 9k (against F. oxysporum and P. glabrum) were found to be highly active at 4 μg/mL with reference to standard amoxicillin and fluconazole. Further, the present synthetic protocol would open new gates for other researchers to develop new molecules by bioisosteres of these substrates. American Chemical Society 2022-04-28 /pmc/articles/PMC9097205/ /pubmed/35571772 http://dx.doi.org/10.1021/acsomega.2c01316 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Malhi, Dharambeer S. Sohal, Harvinder S. Singh, Kishanpal Almarhoon, Zainab M. Bacha, Abir Ben Al-Zaben, Maha I. Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity |
title | Highly Efficient Electrocarboxylation Method to Synthesize
Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their
Antimicrobial Activity |
title_full | Highly Efficient Electrocarboxylation Method to Synthesize
Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their
Antimicrobial Activity |
title_fullStr | Highly Efficient Electrocarboxylation Method to Synthesize
Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their
Antimicrobial Activity |
title_full_unstemmed | Highly Efficient Electrocarboxylation Method to Synthesize
Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their
Antimicrobial Activity |
title_short | Highly Efficient Electrocarboxylation Method to Synthesize
Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their
Antimicrobial Activity |
title_sort | highly efficient electrocarboxylation method to synthesize
novel acid derivatives of 1,4-dihydropyridines and to study their
antimicrobial activity |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9097205/ https://www.ncbi.nlm.nih.gov/pubmed/35571772 http://dx.doi.org/10.1021/acsomega.2c01316 |
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