Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli

A computer-assisted approach was used to model and study privileged heterocyclic scaffolds containing dihydropyrazole, pyrimidin-2-amine, and thiazolidin-4-one moieties (hybrid pharmacophores) to obtain novel and promising antimicrobial prototype molecules. Main bioavailability descriptors were d...

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Autor principal:	Fabián Orozco-López, Liliana Rocío Guerrero Villalobos , Paola Andrea Cuervo Prado
Formato:	article
Lenguaje:	EN ES
Publicado:	Pontificia Universidad Javeriana 2021
Materias:	pbp-3 inhibitors; hybrid pharmacophores; in silico screening; dihydropyrazoles; pyrimidin-2-amines; thiazolidin-4-ones. Science (General) Q1-390
Acceso en línea:	https://doaj.org/article/7bae2324ad9548a98c2a4823fc69d2b4
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spelling	oai:doaj.org-article:7bae2324ad9548a98c2a4823fc69d2b42021-11-17T21:33:32ZComputer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia colidoi.org/10.11144/Javeriana.SC26-1.cads0122-74832027-1352https://doaj.org/article/7bae2324ad9548a98c2a4823fc69d2b42021-07-01T00:00:00Zhttps://revistas.javeriana.edu.co/index.php/scientarium/article/view/28124https://doaj.org/toc/0122-7483https://doaj.org/toc/2027-1352A computer-assisted approach was used to model and study privileged heterocyclic scaffolds containing dihydropyrazole, pyrimidin-2-amine, and thiazolidin-4-one moieties (hybrid pharmacophores) to obtain novel and promising antimicrobial prototype molecules. Main bioavailability descriptors were determined in order to assess the drug-likeness of the designed compounds and to pre-filter eleven compounds exhibiting the best profiles, thus passing to molecular docking study against a key penicillin-binding protein type-3 from enterotoxygenic E. coli. Seven structures were chosen by their energies of affinity and docking interactions with key residues in the active site of the receptor. Seven compounds with the highest docking scores belonging to the series of chalcones, dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones were prepared via condensation or cyclocondensation reactions. The structural elucidation of the final products was carried out by infrared spectra analysis and NMR experiments. Such molecular hybrids considered as potential hits in the search for new antibacterial compounds will be tested in vitro in further studies.Fabián Orozco-López, Liliana Rocío Guerrero Villalobos , Paola Andrea Cuervo PradoPontificia Universidad Javerianaarticlepbp-3 inhibitors; hybrid pharmacophores; in silico screening; dihydropyrazoles; pyrimidin-2-amines; thiazolidin-4-ones.Science (General)Q1-390ENESUniversitas Scientiarum, Vol 26, Iss 1, Pp 17-35 (2021)
institution	DOAJ
collection	DOAJ
language	EN ES
topic	pbp-3 inhibitors; hybrid pharmacophores; in silico screening; dihydropyrazoles; pyrimidin-2-amines; thiazolidin-4-ones. Science (General) Q1-390
spellingShingle	pbp-3 inhibitors; hybrid pharmacophores; in silico screening; dihydropyrazoles; pyrimidin-2-amines; thiazolidin-4-ones. Science (General) Q1-390 Fabián Orozco-López, Liliana Rocío Guerrero Villalobos , Paola Andrea Cuervo Prado Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli
description	A computer-assisted approach was used to model and study privileged heterocyclic scaffolds containing dihydropyrazole, pyrimidin-2-amine, and thiazolidin-4-one moieties (hybrid pharmacophores) to obtain novel and promising antimicrobial prototype molecules. Main bioavailability descriptors were determined in order to assess the drug-likeness of the designed compounds and to pre-filter eleven compounds exhibiting the best profiles, thus passing to molecular docking study against a key penicillin-binding protein type-3 from enterotoxygenic E. coli. Seven structures were chosen by their energies of affinity and docking interactions with key residues in the active site of the receptor. Seven compounds with the highest docking scores belonging to the series of chalcones, dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones were prepared via condensation or cyclocondensation reactions. The structural elucidation of the final products was carried out by infrared spectra analysis and NMR experiments. Such molecular hybrids considered as potential hits in the search for new antibacterial compounds will be tested in vitro in further studies.
format	article
author	Fabián Orozco-López, Liliana Rocío Guerrero Villalobos , Paola Andrea Cuervo Prado
author_facet	Fabián Orozco-López, Liliana Rocío Guerrero Villalobos , Paola Andrea Cuervo Prado
author_sort	Fabián Orozco-López, Liliana Rocío Guerrero Villalobos , Paola Andrea Cuervo Prado
title	Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli
title_short	Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli
title_full	Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli
title_fullStr	Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli
title_full_unstemmed	Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli
title_sort	computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (pbp-3) of escherichia coli
publisher	Pontificia Universidad Javeriana
publishDate	2021
url	https://doaj.org/article/7bae2324ad9548a98c2a4823fc69d2b4
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Computer-aided design, synthesis, and characterization of molecular hybrids of dihydropyrazoles, aminopyrimidines, and thiazolidin-4-ones as potential inhibitors of the penicillin-binding protein 3 (PBP-3) of Escherichia coli

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