4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies
Abstract A series of novel 4-thiazolidinone inhibitors SKYa–SKYg, containing coumarin as a core structure were synthesized via facile and efficient method. The structures of the synthesized compounds were established by extensive spectroscopic studies (FT IR, 1D NMR, 2D NMR, LC–MS) and elemental ana...
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doaj-cc9c1969588740af9f327f8291f4ac462021-08-02T16:50:08ZengBMCChemistry Central Journal1752-153X2018-06-0112111610.1186/s13065-018-0435-04-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studiesSamina Khan Yusufzai0Hasnah Osman1Mohammad Shaheen Khan2Basma M. Abd Razik3Mohammed Oday Ezzat4Suriyati Mohamad5Othman Sulaiman6Jualang Azlan Gansau7Thaigarajan Parumasivam8School of Chemical Sciences, Universiti Sains MalaysiaSchool of Chemical Sciences, Universiti Sains MalaysiaIndustrial Chemistry Programme, Faculty of Science and Natural Resources, Universiti Malaysia SabahCollege of Pharmacy, Al-Mustansiriyah UniversityCollege of Education for Women, University of AnbarSchool of Biological Sciences, Universiti Sains MalaysiaSchool of Industrial Technology, Universiti Sains MalaysiaBiotechnology Programme, Faculty of Science and Natural Resources, Universiti Malaysia SabahSchool of Pharmaceutical Sciences, Universiti Sains MalaysiaAbstract A series of novel 4-thiazolidinone inhibitors SKYa–SKYg, containing coumarin as a core structure were synthesized via facile and efficient method. The structures of the synthesized compounds were established by extensive spectroscopic studies (FT IR, 1D NMR, 2D NMR, LC–MS) and elemental analysis. All the synthesized hybrids were further evaluated for their potential as anti-tubercular agents against Mycobacterium tuberculosis H37Rv ATCC 25618, and anti-bacterial agents against Escherichia coli, Enterobacter aerogenes, Salmonella typhi, Streptococcus pneumoniae and Staphylococcus aureus. Interestingly, the hybrids displayed potent bioactivity. However, compounds SKYc, SKYd, and SKYe appeared to be more effective against the tested bacterial strains, among which compound SKYb showed the highest inhibition against all the bacterial strains ranging from 41 to 165 μg/mL, as compared to the standards, streptomycin, kanamycin and vancomycin. Moreover, derivative SKYa was found to be the strongest against M. tuberculosis (83 μg/mL). Additionally, the anti-dengue potential of the coumarin hybrids as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors was calculated using computational molecular docking approach, with reference to the standards 4-hydroxypanduratin, panduratin and ethyl 3-(4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy)propanoate with DS of − 3.379, − 3.189 and − 3.381, respectively. The docking results revealed that the synthesized hybrids exhibited potent anti-dengue activity among which compounds SKYf, SKYd, SKYc and SKYe were found to be the best ones with docking scores of − 4.014, − 3.964, − 3.905 and − 3.889. In summary, we discovered 4-thiazolidinone coumarin derivatives as a new scaffold that may eventually yield useful compounds in the treatment of bacterial and viral infections.http://link.springer.com/article/10.1186/s13065-018-0435-0Molecular dockingAnti-bacterialAnti-tuberculosisAnti-viralAnti-dengueCoumarin thiazolidinone |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Samina Khan Yusufzai Hasnah Osman Mohammad Shaheen Khan Basma M. Abd Razik Mohammed Oday Ezzat Suriyati Mohamad Othman Sulaiman Jualang Azlan Gansau Thaigarajan Parumasivam |
spellingShingle |
Samina Khan Yusufzai Hasnah Osman Mohammad Shaheen Khan Basma M. Abd Razik Mohammed Oday Ezzat Suriyati Mohamad Othman Sulaiman Jualang Azlan Gansau Thaigarajan Parumasivam 4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies Chemistry Central Journal Molecular docking Anti-bacterial Anti-tuberculosis Anti-viral Anti-dengue Coumarin thiazolidinone |
author_facet |
Samina Khan Yusufzai Hasnah Osman Mohammad Shaheen Khan Basma M. Abd Razik Mohammed Oday Ezzat Suriyati Mohamad Othman Sulaiman Jualang Azlan Gansau Thaigarajan Parumasivam |
author_sort |
Samina Khan Yusufzai |
title |
4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies |
title_short |
4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies |
title_full |
4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies |
title_fullStr |
4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies |
title_full_unstemmed |
4-Thiazolidinone coumarin derivatives as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies |
title_sort |
4-thiazolidinone coumarin derivatives as two-component ns2b/ns3 denv flavivirus serine protease inhibitors: synthesis, molecular docking, biological evaluation and structure–activity relationship studies |
publisher |
BMC |
series |
Chemistry Central Journal |
issn |
1752-153X |
publishDate |
2018-06-01 |
description |
Abstract A series of novel 4-thiazolidinone inhibitors SKYa–SKYg, containing coumarin as a core structure were synthesized via facile and efficient method. The structures of the synthesized compounds were established by extensive spectroscopic studies (FT IR, 1D NMR, 2D NMR, LC–MS) and elemental analysis. All the synthesized hybrids were further evaluated for their potential as anti-tubercular agents against Mycobacterium tuberculosis H37Rv ATCC 25618, and anti-bacterial agents against Escherichia coli, Enterobacter aerogenes, Salmonella typhi, Streptococcus pneumoniae and Staphylococcus aureus. Interestingly, the hybrids displayed potent bioactivity. However, compounds SKYc, SKYd, and SKYe appeared to be more effective against the tested bacterial strains, among which compound SKYb showed the highest inhibition against all the bacterial strains ranging from 41 to 165 μg/mL, as compared to the standards, streptomycin, kanamycin and vancomycin. Moreover, derivative SKYa was found to be the strongest against M. tuberculosis (83 μg/mL). Additionally, the anti-dengue potential of the coumarin hybrids as two-component NS2B/NS3 DENV flavivirus serine protease inhibitors was calculated using computational molecular docking approach, with reference to the standards 4-hydroxypanduratin, panduratin and ethyl 3-(4-(hydroxymethyl)-2-methoxy-5-nitrophenoxy)propanoate with DS of − 3.379, − 3.189 and − 3.381, respectively. The docking results revealed that the synthesized hybrids exhibited potent anti-dengue activity among which compounds SKYf, SKYd, SKYc and SKYe were found to be the best ones with docking scores of − 4.014, − 3.964, − 3.905 and − 3.889. In summary, we discovered 4-thiazolidinone coumarin derivatives as a new scaffold that may eventually yield useful compounds in the treatment of bacterial and viral infections. |
topic |
Molecular docking Anti-bacterial Anti-tuberculosis Anti-viral Anti-dengue Coumarin thiazolidinone |
url |
http://link.springer.com/article/10.1186/s13065-018-0435-0 |
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