Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies
We synthesized a series of compounds bearing pharmacologically important 1,3,4-oxadiazole and piperidine moieties. Spectral data analysis by 1H-NMR, 13C-NMR, IR and EI-MS was used to elucidate the structures of the synthesized molecules. Docking studies explained the different types of interaction o...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Universidade de São Paulo
2020-12-01
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| Series: | Brazilian Journal of Pharmaceutical Sciences |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S1984-82502020000100596&tlng=en |
| _version_ | 1818367801889390592 |
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| author | Javed Iqbal Aziz-ur- Rehman Muhammad Athar Abbasi Sabahat Zahra Siddiqui Shahid Rasool Muhammad Ashraf Ambar Iqbal Sujhla Hamid Tahir Ali Chohan Hira Khalid Sabina Jhaumeer Laulloo Syed Adnan Ali Shah |
| author_facet | Javed Iqbal Aziz-ur- Rehman Muhammad Athar Abbasi Sabahat Zahra Siddiqui Shahid Rasool Muhammad Ashraf Ambar Iqbal Sujhla Hamid Tahir Ali Chohan Hira Khalid Sabina Jhaumeer Laulloo Syed Adnan Ali Shah |
| author_sort | Javed Iqbal |
| collection | DOAJ |
| description | We synthesized a series of compounds bearing pharmacologically important 1,3,4-oxadiazole and piperidine moieties. Spectral data analysis by 1H-NMR, 13C-NMR, IR and EI-MS was used to elucidate the structures of the synthesized molecules. Docking studies explained the different types of interaction of the compounds with amino acids, while bovine serum albumin (BSA) binding interactions showed their pharmacological effectiveness. Antibacterial screening of these compounds demonstrated moderate to strong activity against Salmonella typhi and Bacillus subtilis but only weak to moderate activity against the other three bacterial strains tested. Seven compounds were the most active members as acetyl cholinesterase inhibitors. All the compounds presented displayed strong inhibitory activity against urease. Compounds 7l, 7m, 7n, 7o, 7p, 7r, 7u, 7v, 7x and 7v were highly active, with respective IC50 values of 2.14±0.003, 0.63±0.001, 2.17±0.006, 1.13±0.003, 1.21±0.005, 6.28±0.003, 2.39±0.005, 2.15±0.002, 2.26±0.003 and 2.14±0.002 µM, compared to thiourea, used as the reference standard (IC50 = 21.25±0.15 µM). These new urease inhibitors could replace existing drugs after their evaluation in comprehensive in vivo studies. |
| first_indexed | 2024-12-13T22:57:50Z |
| format | Article |
| id | doaj.art-1cfa670315a84bd18614836253adea14 |
| institution | Directory Open Access Journal |
| issn | 2175-9790 |
| language | English |
| last_indexed | 2024-12-13T22:57:50Z |
| publishDate | 2020-12-01 |
| publisher | Universidade de São Paulo |
| record_format | Article |
| series | Brazilian Journal of Pharmaceutical Sciences |
| spelling | doaj.art-1cfa670315a84bd18614836253adea142022-12-21T23:28:28ZengUniversidade de São PauloBrazilian Journal of Pharmaceutical Sciences2175-97902020-12-015610.1590/s2175-97902020000118092Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studiesJaved IqbalAziz-ur- Rehmanhttps://orcid.org/0000-0002-0262-7726Muhammad Athar AbbasiSabahat Zahra SiddiquiShahid RasoolMuhammad AshrafAmbar IqbalSujhla HamidTahir Ali ChohanHira KhalidSabina Jhaumeer LaullooSyed Adnan Ali ShahWe synthesized a series of compounds bearing pharmacologically important 1,3,4-oxadiazole and piperidine moieties. Spectral data analysis by 1H-NMR, 13C-NMR, IR and EI-MS was used to elucidate the structures of the synthesized molecules. Docking studies explained the different types of interaction of the compounds with amino acids, while bovine serum albumin (BSA) binding interactions showed their pharmacological effectiveness. Antibacterial screening of these compounds demonstrated moderate to strong activity against Salmonella typhi and Bacillus subtilis but only weak to moderate activity against the other three bacterial strains tested. Seven compounds were the most active members as acetyl cholinesterase inhibitors. All the compounds presented displayed strong inhibitory activity against urease. Compounds 7l, 7m, 7n, 7o, 7p, 7r, 7u, 7v, 7x and 7v were highly active, with respective IC50 values of 2.14±0.003, 0.63±0.001, 2.17±0.006, 1.13±0.003, 1.21±0.005, 6.28±0.003, 2.39±0.005, 2.15±0.002, 2.26±0.003 and 2.14±0.002 µM, compared to thiourea, used as the reference standard (IC50 = 21.25±0.15 µM). These new urease inhibitors could replace existing drugs after their evaluation in comprehensive in vivo studies.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S1984-82502020000100596&tlng=en1,3,4-OxadiazoleAcetylcholinesterase (AChE) inhibitionAntibacterial activityPiperidineSulfonamideUrease inhibition |
| spellingShingle | Javed Iqbal Aziz-ur- Rehman Muhammad Athar Abbasi Sabahat Zahra Siddiqui Shahid Rasool Muhammad Ashraf Ambar Iqbal Sujhla Hamid Tahir Ali Chohan Hira Khalid Sabina Jhaumeer Laulloo Syed Adnan Ali Shah Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies Brazilian Journal of Pharmaceutical Sciences 1,3,4-Oxadiazole Acetylcholinesterase (AChE) inhibition Antibacterial activity Piperidine Sulfonamide Urease inhibition |
| title | Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies |
| title_full | Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies |
| title_fullStr | Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies |
| title_full_unstemmed | Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies |
| title_short | Biological activity of synthesized 5-{1-[(4-chlorophenyl)sulfonyl]piperidin-4-yl}-2-mercapto-1,3,4-oxadiazole derivatives demonstrated by in silico and BSA binding studies |
| title_sort | biological activity of synthesized 5 1 4 chlorophenyl sulfonyl piperidin 4 yl 2 mercapto 1 3 4 oxadiazole derivatives demonstrated by in silico and bsa binding studies |
| topic | 1,3,4-Oxadiazole Acetylcholinesterase (AChE) inhibition Antibacterial activity Piperidine Sulfonamide Urease inhibition |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S1984-82502020000100596&tlng=en |
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