Cargando…
Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives
Nitro-containing heteroaromatic derivatives structurally related to nitroimidazole (Metronidazole) are being extensively evaluated against Helicobacter pylori isolates. On the other hand, 1,3,4-thiadiazole derivatives have also demonstrated promising antibacterial potential. In present study, we eva...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Shaheed Beheshti University of Medical Sciences
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813270/ https://www.ncbi.nlm.nih.gov/pubmed/24250634 |
_version_ | 1782289087183454208 |
---|---|
author | Asadipour, Ali Edraki, Najmeh Nakhjiri, Maryam Yahya-Meymandi, Azadeh Alipour, Eskandar Saniee, Parastoo Siavoshi, Farideh Shafiee, Abbas Foroumadi, Alireza |
author_facet | Asadipour, Ali Edraki, Najmeh Nakhjiri, Maryam Yahya-Meymandi, Azadeh Alipour, Eskandar Saniee, Parastoo Siavoshi, Farideh Shafiee, Abbas Foroumadi, Alireza |
author_sort | Asadipour, Ali |
collection | PubMed |
description | Nitro-containing heteroaromatic derivatives structurally related to nitroimidazole (Metronidazole) are being extensively evaluated against Helicobacter pylori isolates. On the other hand, 1,3,4-thiadiazole derivatives have also demonstrated promising antibacterial potential. In present study, we evaluated anti-H. pylori activity of novel hybrid molecules bearing nitroaryl and 1,3,4-thiadiazole moieties. Anti-H. pylori activity of novel 5-(5-nitroaryl)-1,3,4-thiadiazole derivatives bearing different bulky alkylthio side chains at C-2 position of thiadiazole ring, were assessed against three different metronidazole resistant H. pylori isolates by paper disk diffusion method. Most of the compounds demonstrated moderate to strong inhibitory response especially at 25 μg/disk. The structure-activity relationship study of the compounds demonstrated that introduction of different alkylthio moieties at C-2 position of thiadiazole ring; alter the inhibitory activity which is mainly dependent on the type of C-5 attached nitrohetercyclic ring. The promising compound of this scaffold, bearing 1-methyl-5-nitroimidazole moiety at C-5 and α-methylbenzylthio side chain at C-2 position of thiadiazole ring, showed strong inhibitory response against metronidazole resistant H. pylori isolates at 12.5 μg/disk (the inhibition zone diameter at all evaluated concentrations (12.5- 100 μg/disk) is >50 mm). Novel 5-(5-nitroaryl)-1,3,4-thiadiazole scaffold bearing different C-2 attached thio-pendant moieties with promising anti-H. pylori potential were identified. Among different nitroheterocycles, 5-nitrofuran and 5-nitroimidazole moieties were preferable for the substitution at C-5 position of 1,3,4-thiadiazole ring. Introduction of different alkylthio side chains at C-2 position of central ring alter the inhibitory activity which is mainly dependent on the type of C-5 attached nitrohetercyclic ring. |
format | Online Article Text |
id | pubmed-3813270 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Shaheed Beheshti University of Medical Sciences |
record_format | MEDLINE/PubMed |
spelling | pubmed-38132702013-11-18 Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives Asadipour, Ali Edraki, Najmeh Nakhjiri, Maryam Yahya-Meymandi, Azadeh Alipour, Eskandar Saniee, Parastoo Siavoshi, Farideh Shafiee, Abbas Foroumadi, Alireza Iran J Pharm Res Original Article Nitro-containing heteroaromatic derivatives structurally related to nitroimidazole (Metronidazole) are being extensively evaluated against Helicobacter pylori isolates. On the other hand, 1,3,4-thiadiazole derivatives have also demonstrated promising antibacterial potential. In present study, we evaluated anti-H. pylori activity of novel hybrid molecules bearing nitroaryl and 1,3,4-thiadiazole moieties. Anti-H. pylori activity of novel 5-(5-nitroaryl)-1,3,4-thiadiazole derivatives bearing different bulky alkylthio side chains at C-2 position of thiadiazole ring, were assessed against three different metronidazole resistant H. pylori isolates by paper disk diffusion method. Most of the compounds demonstrated moderate to strong inhibitory response especially at 25 μg/disk. The structure-activity relationship study of the compounds demonstrated that introduction of different alkylthio moieties at C-2 position of thiadiazole ring; alter the inhibitory activity which is mainly dependent on the type of C-5 attached nitrohetercyclic ring. The promising compound of this scaffold, bearing 1-methyl-5-nitroimidazole moiety at C-5 and α-methylbenzylthio side chain at C-2 position of thiadiazole ring, showed strong inhibitory response against metronidazole resistant H. pylori isolates at 12.5 μg/disk (the inhibition zone diameter at all evaluated concentrations (12.5- 100 μg/disk) is >50 mm). Novel 5-(5-nitroaryl)-1,3,4-thiadiazole scaffold bearing different C-2 attached thio-pendant moieties with promising anti-H. pylori potential were identified. Among different nitroheterocycles, 5-nitrofuran and 5-nitroimidazole moieties were preferable for the substitution at C-5 position of 1,3,4-thiadiazole ring. Introduction of different alkylthio side chains at C-2 position of central ring alter the inhibitory activity which is mainly dependent on the type of C-5 attached nitrohetercyclic ring. Shaheed Beheshti University of Medical Sciences 2013 /pmc/articles/PMC3813270/ /pubmed/24250634 Text en © 2013 by School of Pharmacy, Shaheed Beheshti University of Medical Sciences and Health Services 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 Asadipour, Ali Edraki, Najmeh Nakhjiri, Maryam Yahya-Meymandi, Azadeh Alipour, Eskandar Saniee, Parastoo Siavoshi, Farideh Shafiee, Abbas Foroumadi, Alireza Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives |
title | Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives |
title_full | Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives |
title_fullStr | Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives |
title_full_unstemmed | Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives |
title_short | Anti-Helicobacter pylori activity and Structure-Activity Relationship study of 2-Alkylthio-5-(nitroaryl)-1,3,4-thiadiazole Derivatives |
title_sort | anti-helicobacter pylori activity and structure-activity relationship study of 2-alkylthio-5-(nitroaryl)-1,3,4-thiadiazole derivatives |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3813270/ https://www.ncbi.nlm.nih.gov/pubmed/24250634 |
work_keys_str_mv | AT asadipourali antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT edrakinajmeh antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT nakhjirimaryam antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT yahyameymandiazadeh antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT alipoureskandar antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT sanieeparastoo antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT siavoshifarideh antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT shafieeabbas antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives AT foroumadialireza antihelicobacterpyloriactivityandstructureactivityrelationshipstudyof2alkylthio5nitroaryl134thiadiazolederivatives |