Cargando…
Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives
A series of novel 4-anilinoquinazoline derivatives were designed and synthesized from benzoic acid through ring closure, chlorination or nucleophilic substitution. The structures of compounds were characterized by IR, (1)H-NMR and mass spectroscopy. All synthesized derivatives were screened for thei...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Medknow Publications & Media Pvt Ltd
2017
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5615873/ https://www.ncbi.nlm.nih.gov/pubmed/28974981 http://dx.doi.org/10.4103/1735-5362.213988 |
_version_ | 1783266680659509248 |
---|---|
author | Nasab, Rezvan Rezaee Hassanzadeh, Farshid Khodarahmi, Ghadam Ali Rostami, Mahboubeh Mirzaei, Mahmoud Jahanian-Najafabadi, Ali Mansourian, Mahboubeh |
author_facet | Nasab, Rezvan Rezaee Hassanzadeh, Farshid Khodarahmi, Ghadam Ali Rostami, Mahboubeh Mirzaei, Mahmoud Jahanian-Najafabadi, Ali Mansourian, Mahboubeh |
author_sort | Nasab, Rezvan Rezaee |
collection | PubMed |
description | A series of novel 4-anilinoquinazoline derivatives were designed and synthesized from benzoic acid through ring closure, chlorination or nucleophilic substitution. The structures of compounds were characterized by IR, (1)H-NMR and mass spectroscopy. All synthesized derivatives were screened for their antimicrobial activities against Gram-positive (Staphylococcus aurous, Bacillus subtilis, Listeria monocitogenes) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Salmonella entritidis) bacteria and also for antifungal activities against Candida albicans using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially compound 4c having highest activities against E. coli at 32 μg/mL concentration while the tested compounds did not exhibited remarkable antifungal activities. The potential DNA gyrase inhibitory activity of these compounds was investigated in silico using molecular docking simulation method. All compounds showed good results especially compound 4c which showed the lowest ΔG(bind) results (-8.16 Kcal/mol). |
format | Online Article Text |
id | pubmed-5615873 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Medknow Publications & Media Pvt Ltd |
record_format | MEDLINE/PubMed |
spelling | pubmed-56158732017-10-04 Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives Nasab, Rezvan Rezaee Hassanzadeh, Farshid Khodarahmi, Ghadam Ali Rostami, Mahboubeh Mirzaei, Mahmoud Jahanian-Najafabadi, Ali Mansourian, Mahboubeh Res Pharm Sci Original Article A series of novel 4-anilinoquinazoline derivatives were designed and synthesized from benzoic acid through ring closure, chlorination or nucleophilic substitution. The structures of compounds were characterized by IR, (1)H-NMR and mass spectroscopy. All synthesized derivatives were screened for their antimicrobial activities against Gram-positive (Staphylococcus aurous, Bacillus subtilis, Listeria monocitogenes) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Salmonella entritidis) bacteria and also for antifungal activities against Candida albicans using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially compound 4c having highest activities against E. coli at 32 μg/mL concentration while the tested compounds did not exhibited remarkable antifungal activities. The potential DNA gyrase inhibitory activity of these compounds was investigated in silico using molecular docking simulation method. All compounds showed good results especially compound 4c which showed the lowest ΔG(bind) results (-8.16 Kcal/mol). Medknow Publications & Media Pvt Ltd 2017-10 /pmc/articles/PMC5615873/ /pubmed/28974981 http://dx.doi.org/10.4103/1735-5362.213988 Text en Copyright: © 2017 Research in Pharmaceutical Sciences http://creativecommons.org/licenses/by-nc-sa/3.0 This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 License, which allows others to remix, tweak, and build upon the work non-commercially, as long as the author is credited and the new creations are licensed under the identical terms. |
spellingShingle | Original Article Nasab, Rezvan Rezaee Hassanzadeh, Farshid Khodarahmi, Ghadam Ali Rostami, Mahboubeh Mirzaei, Mahmoud Jahanian-Najafabadi, Ali Mansourian, Mahboubeh Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
title | Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
title_full | Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
title_fullStr | Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
title_full_unstemmed | Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
title_short | Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
title_sort | docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5615873/ https://www.ncbi.nlm.nih.gov/pubmed/28974981 http://dx.doi.org/10.4103/1735-5362.213988 |
work_keys_str_mv | AT nasabrezvanrezaee dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives AT hassanzadehfarshid dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives AT khodarahmighadamali dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives AT rostamimahboubeh dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives AT mirzaeimahmoud dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives AT jahaniannajafabadiali dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives AT mansourianmahboubeh dockingstudysynthesisandantimicrobialevaluationofsomenovel4anilinoquinazolinederivatives |