Cargando…
Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents
A novel one-pot two step tandem reaction for the synthesis of indolizine-1-carbonitrile derivatives (5a-i) was identified. The route comprises 1,3-dipolar cycloaddition reaction of aromatic aldehyde derivatives (1a-i), malononitrile (2) and 1-(2-(4-bromophenyl)-2-oxoethyl)-2-chloropyridin-1-ium (4)...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Shaheed Beheshti University of Medical Sciences
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6094435/ https://www.ncbi.nlm.nih.gov/pubmed/30127812 |
_version_ | 1783347815071612928 |
---|---|
author | Faghih-Mirzaei, Ehsan Seifi, Mohammad Abaszadeh, Mehdi Zomorodian, Kamiar Helali, Helia |
author_facet | Faghih-Mirzaei, Ehsan Seifi, Mohammad Abaszadeh, Mehdi Zomorodian, Kamiar Helali, Helia |
author_sort | Faghih-Mirzaei, Ehsan |
collection | PubMed |
description | A novel one-pot two step tandem reaction for the synthesis of indolizine-1-carbonitrile derivatives (5a-i) was identified. The route comprises 1,3-dipolar cycloaddition reaction of aromatic aldehyde derivatives (1a-i), malononitrile (2) and 1-(2-(4-bromophenyl)-2-oxoethyl)-2-chloropyridin-1-ium (4) under ultrasound irradiation at room temperature in the presence of triethylamine at acetonitrile. The product compounds were tested against bacteria and fungi. It was revealed that compound 5b had the most antifungal activity (range MICs = 8–32 µg/mL) and compound 5g had the most antibacterial activity (range MICs = 16–256 µg/mL). Molecular docking of compounds (5a-i) into fungal 14α-demethylase and bacterial protein tyrosine phosphatase active sites were also performed and probable binding mode of compounds 5b and 5g were determined. |
format | Online Article Text |
id | pubmed-6094435 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Shaheed Beheshti University of Medical Sciences |
record_format | MEDLINE/PubMed |
spelling | pubmed-60944352018-08-20 Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents Faghih-Mirzaei, Ehsan Seifi, Mohammad Abaszadeh, Mehdi Zomorodian, Kamiar Helali, Helia Iran J Pharm Res Original Article A novel one-pot two step tandem reaction for the synthesis of indolizine-1-carbonitrile derivatives (5a-i) was identified. The route comprises 1,3-dipolar cycloaddition reaction of aromatic aldehyde derivatives (1a-i), malononitrile (2) and 1-(2-(4-bromophenyl)-2-oxoethyl)-2-chloropyridin-1-ium (4) under ultrasound irradiation at room temperature in the presence of triethylamine at acetonitrile. The product compounds were tested against bacteria and fungi. It was revealed that compound 5b had the most antifungal activity (range MICs = 8–32 µg/mL) and compound 5g had the most antibacterial activity (range MICs = 16–256 µg/mL). Molecular docking of compounds (5a-i) into fungal 14α-demethylase and bacterial protein tyrosine phosphatase active sites were also performed and probable binding mode of compounds 5b and 5g were determined. Shaheed Beheshti University of Medical Sciences 2018 /pmc/articles/PMC6094435/ /pubmed/30127812 Text en This is an Open Access article distributed under the terms of the Creative Commons Attribution License, (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Original Article Faghih-Mirzaei, Ehsan Seifi, Mohammad Abaszadeh, Mehdi Zomorodian, Kamiar Helali, Helia Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents |
title | Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents |
title_full | Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents |
title_fullStr | Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents |
title_full_unstemmed | Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents |
title_short | Design, Synthesis, Biological Evaluation and Molecular Modeling Study of Novel Indolizine-1-Carbonitrile Derivatives as Potential Anti-Microbial Agents |
title_sort | design, synthesis, biological evaluation and molecular modeling study of novel indolizine-1-carbonitrile derivatives as potential anti-microbial agents |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6094435/ https://www.ncbi.nlm.nih.gov/pubmed/30127812 |
work_keys_str_mv | AT faghihmirzaeiehsan designsynthesisbiologicalevaluationandmolecularmodelingstudyofnovelindolizine1carbonitrilederivativesaspotentialantimicrobialagents AT seifimohammad designsynthesisbiologicalevaluationandmolecularmodelingstudyofnovelindolizine1carbonitrilederivativesaspotentialantimicrobialagents AT abaszadehmehdi designsynthesisbiologicalevaluationandmolecularmodelingstudyofnovelindolizine1carbonitrilederivativesaspotentialantimicrobialagents AT zomorodiankamiar designsynthesisbiologicalevaluationandmolecularmodelingstudyofnovelindolizine1carbonitrilederivativesaspotentialantimicrobialagents AT helalihelia designsynthesisbiologicalevaluationandmolecularmodelingstudyofnovelindolizine1carbonitrilederivativesaspotentialantimicrobialagents |