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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...

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Autores principales: Malhi, Dharambeer S., Sohal, Harvinder S., Singh, Kishanpal, Almarhoon, Zainab M., Bacha, Abir Ben, Al-Zaben, Maha I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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.
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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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