Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis
Antimicrobial resistance (AMR) compelled scientists in general while pharmacists, chemists and biologists in specific to believe that we could always remain ahead of the pathogens. The pipeline of new drugs is running gasping and the inducements to develop new antimicrobials to address the global pr...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2019-11-01
|
| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844019364722 |
| _version_ | 1818057438019977216 |
|---|---|
| author | Mumtaz Hussain Tahir Qadri Zahid Hussain Aamer Saeed Pervaiz Ali Channar Syeda Aaliya Shehzadi Mubashir Hassan Fayaz Ali Larik Tarique Mahmood Arif Malik |
| author_facet | Mumtaz Hussain Tahir Qadri Zahid Hussain Aamer Saeed Pervaiz Ali Channar Syeda Aaliya Shehzadi Mubashir Hassan Fayaz Ali Larik Tarique Mahmood Arif Malik |
| author_sort | Mumtaz Hussain |
| collection | DOAJ |
| description | Antimicrobial resistance (AMR) compelled scientists in general while pharmacists, chemists and biologists in specific to believe that we could always remain ahead of the pathogens. The pipeline of new drugs is running gasping and the inducements to develop new antimicrobials to address the global problems of drug resistance are weak. In this pursuit, effective endeavours to prepare new anti-bacterial entities is highly wished. The present study demonstrates successful synthesis of a library of 1,4-disbustituted 1,2,3-triazoles (3a-3k) using Click-chemistry concept and anti-their bacterial potential. In this 1,3-dipolar cycloaddition, the 3-methoxy-4-(prop-2-yn-1-yloxy)benzaldehyde (1) was used as alkyne partner which was synthesized from vanillin and propargyl bromide and further reacted with differently substituted arylpropoxy azides (2a-k) to furnish series of mono and bis1,4-disubstituted-1,2,3-triazoles. All the synthesized compounds were characterized spectroscopically and were evaluated for their initial antimicrobial activity. Preliminary results of antibacterial screening revealed that the synthesized compounds have the highest inhibitory effects compare to the control ciprofloxacin. The compounds 3b and 3g were found to be the most active (MIC: 5 μg/mL, MIC: 10 μg/mL respectively) against various strains of gram-positive and gram-negative bacteria. The molecular docking study against 4GQQ protein with synthesized ligands was performed to see the necessary interactions responsible for anti-bacterial activity. The docking analysis of the most potent compound 3g supported the antibacterial activity exhibiting high inhibition constant and binding energy. |
| first_indexed | 2024-12-10T12:44:44Z |
| format | Article |
| id | doaj.art-a6bd8ad4099c4dc5b28833bf5efab0b1 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-10T12:44:44Z |
| publishDate | 2019-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-a6bd8ad4099c4dc5b28833bf5efab0b12022-12-22T01:48:26ZengElsevierHeliyon2405-84402019-11-01511e02812Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesisMumtaz Hussain0Tahir Qadri1Zahid Hussain2Aamer Saeed3Pervaiz Ali Channar4Syeda Aaliya Shehzadi5Mubashir Hassan6Fayaz Ali Larik7Tarique Mahmood8Arif Malik9Department of Chemistry, University of Karachi, 75270, Karachi, PakistanDepartment of Chemistry, University of Karachi, 75270, Karachi, PakistanDepartment of Chemistry, University of Karachi, 75270, Karachi, PakistanDepartment of Chemistry, Quaid-i-Azam University, 45320, Islamabad, Pakistan; Corresponding author.Department of Chemistry, Quaid-i-Azam University, 45320, Islamabad, PakistanSulaiman Bin Abdullah Aba Al-Khail-Centre for Interdisciplinary Research in Basic Sciences (SA-CIRBS), International Islamic University, 44000, Islamabad, Pakistan; Corresponding author.Institute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road Campus, Lahore, PakistanDepartment of Chemistry, Quaid-i-Azam University, 45320, Islamabad, PakistanDepartment of Chemistry, University of Karachi, 75270, Karachi, PakistanInstitute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road Campus, Lahore, PakistanAntimicrobial resistance (AMR) compelled scientists in general while pharmacists, chemists and biologists in specific to believe that we could always remain ahead of the pathogens. The pipeline of new drugs is running gasping and the inducements to develop new antimicrobials to address the global problems of drug resistance are weak. In this pursuit, effective endeavours to prepare new anti-bacterial entities is highly wished. The present study demonstrates successful synthesis of a library of 1,4-disbustituted 1,2,3-triazoles (3a-3k) using Click-chemistry concept and anti-their bacterial potential. In this 1,3-dipolar cycloaddition, the 3-methoxy-4-(prop-2-yn-1-yloxy)benzaldehyde (1) was used as alkyne partner which was synthesized from vanillin and propargyl bromide and further reacted with differently substituted arylpropoxy azides (2a-k) to furnish series of mono and bis1,4-disubstituted-1,2,3-triazoles. All the synthesized compounds were characterized spectroscopically and were evaluated for their initial antimicrobial activity. Preliminary results of antibacterial screening revealed that the synthesized compounds have the highest inhibitory effects compare to the control ciprofloxacin. The compounds 3b and 3g were found to be the most active (MIC: 5 μg/mL, MIC: 10 μg/mL respectively) against various strains of gram-positive and gram-negative bacteria. The molecular docking study against 4GQQ protein with synthesized ligands was performed to see the necessary interactions responsible for anti-bacterial activity. The docking analysis of the most potent compound 3g supported the antibacterial activity exhibiting high inhibition constant and binding energy.http://www.sciencedirect.com/science/article/pii/S2405844019364722Organic chemistryPharmaceutical chemistryClick chemistry1,4-Disubstituted 1,2,3-triazolesAntibacterial agentsMolecular docking |
| spellingShingle | Mumtaz Hussain Tahir Qadri Zahid Hussain Aamer Saeed Pervaiz Ali Channar Syeda Aaliya Shehzadi Mubashir Hassan Fayaz Ali Larik Tarique Mahmood Arif Malik Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis Heliyon Organic chemistry Pharmaceutical chemistry Click chemistry 1,4-Disubstituted 1,2,3-triazoles Antibacterial agents Molecular docking |
| title | Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis |
| title_full | Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis |
| title_fullStr | Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis |
| title_full_unstemmed | Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis |
| title_short | Synthesis, antibacterial activity and molecular docking study of vanillin derived 1,4-disubstituted 1,2,3-triazoles as inhibitors of bacterial DNA synthesis |
| title_sort | synthesis antibacterial activity and molecular docking study of vanillin derived 1 4 disubstituted 1 2 3 triazoles as inhibitors of bacterial dna synthesis |
| topic | Organic chemistry Pharmaceutical chemistry Click chemistry 1,4-Disubstituted 1,2,3-triazoles Antibacterial agents Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S2405844019364722 |
| work_keys_str_mv | AT mumtazhussain synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT tahirqadri synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT zahidhussain synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT aamersaeed synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT pervaizalichannar synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT syedaaaliyashehzadi synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT mubashirhassan synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT fayazalilarik synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT tariquemahmood synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis AT arifmalik synthesisantibacterialactivityandmoleculardockingstudyofvanillinderived14disubstituted123triazolesasinhibitorsofbacterialdnasynthesis |