Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids
Sulphonamide and 1,3,4-oxadiazole moieties are present as integral structural parts of many drugs and pharmaceuticals. Taking into account the significance of these moieties, we herein present the synthesis, single-crystal X-ray analysis, DFT studies, and α-amylase inhibition of probenecid derived t...
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Taylor & Francis Group
2022-12-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | https://www.tandfonline.com/doi/10.1080/14756366.2022.2078969 |
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| author | Bilal Ahmad Khan Syeda Shamila Hamdani Muhammad Naeem Ahmed Shahid Hameed Muhammad Ashfaq Ahmed M. Shawky Mahmoud A. A. Ibrahim Peter A. Sidhom |
| author_facet | Bilal Ahmad Khan Syeda Shamila Hamdani Muhammad Naeem Ahmed Shahid Hameed Muhammad Ashfaq Ahmed M. Shawky Mahmoud A. A. Ibrahim Peter A. Sidhom |
| author_sort | Bilal Ahmad Khan |
| collection | DOAJ |
| description | Sulphonamide and 1,3,4-oxadiazole moieties are present as integral structural parts of many drugs and pharmaceuticals. Taking into account the significance of these moieties, we herein present the synthesis, single-crystal X-ray analysis, DFT studies, and α-amylase inhibition of probenecid derived two S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids. The synthesis has been accomplished in high yields. The final structures of both hybrids have been established completely with the help of different spectro-analytical techniques, including NMR, FTIR, HR-MS, and single-crystal X-ray diffraction analyses. In an effort to confirm the experimental findings, versatile quantum mechanical calculations and Hirshfeld Surface analysis have been performed. α-Amylase inhibition assay has been executed to investigate the enzyme inhibitory potential of both hybrids. The low IC50 value (76.92 ± 0.19 μg/mL) of hybrid 2 shows the good α-amylase inhibition potential of the respective compound. Ultimately, the binding affinities and features of the two hybrids are elucidated utilising a molecular docking technique against the α-amylase enzyme. |
| format | Article |
| id | doaj-art-0c30a4906dfd440bae3f0be210e1fa42 |
| institution | DOAJ |
| issn | 1475-6366 1475-6374 |
| language | English |
| publishDate | 2022-12-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj-art-0c30a4906dfd440bae3f0be210e1fa422025-08-20T03:22:15ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742022-12-013711464147810.1080/14756366.2022.2078969Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybridsBilal Ahmad Khan0Syeda Shamila Hamdani1Muhammad Naeem Ahmed2Shahid Hameed3Muhammad Ashfaq4Ahmed M. Shawky5Mahmoud A. A. Ibrahim6Peter A. Sidhom7Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad, PakistanDepartment of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad, PakistanDepartment of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad, PakistanDepartment of Physics, University of Sargodha, Sargodha, PakistanScience and Technology Unit (STU), Umm Al-Qura University, Makkah, Saudi ArabiaComputational Chemistry Laboratory, Chemistry Department, Faculty of Science, Minia University, Minia, EgyptDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta, EgyptSulphonamide and 1,3,4-oxadiazole moieties are present as integral structural parts of many drugs and pharmaceuticals. Taking into account the significance of these moieties, we herein present the synthesis, single-crystal X-ray analysis, DFT studies, and α-amylase inhibition of probenecid derived two S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids. The synthesis has been accomplished in high yields. The final structures of both hybrids have been established completely with the help of different spectro-analytical techniques, including NMR, FTIR, HR-MS, and single-crystal X-ray diffraction analyses. In an effort to confirm the experimental findings, versatile quantum mechanical calculations and Hirshfeld Surface analysis have been performed. α-Amylase inhibition assay has been executed to investigate the enzyme inhibitory potential of both hybrids. The low IC50 value (76.92 ± 0.19 μg/mL) of hybrid 2 shows the good α-amylase inhibition potential of the respective compound. Ultimately, the binding affinities and features of the two hybrids are elucidated utilising a molecular docking technique against the α-amylase enzyme.https://www.tandfonline.com/doi/10.1080/14756366.2022.2078969OxadiazoleprobenecidX-ray diffractionenzyme inhibitionmolecular modelling |
| spellingShingle | Bilal Ahmad Khan Syeda Shamila Hamdani Muhammad Naeem Ahmed Shahid Hameed Muhammad Ashfaq Ahmed M. Shawky Mahmoud A. A. Ibrahim Peter A. Sidhom Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids Journal of Enzyme Inhibition and Medicinal Chemistry Oxadiazole probenecid X-ray diffraction enzyme inhibition molecular modelling |
| title | Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids |
| title_full | Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids |
| title_fullStr | Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids |
| title_full_unstemmed | Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids |
| title_short | Synthesis, X-ray diffraction analysis, quantum chemical studies and α-amylase inhibition of probenecid derived S-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids |
| title_sort | synthesis x ray diffraction analysis quantum chemical studies and α amylase inhibition of probenecid derived s alkylphthalimide oxadiazole benzenesulfonamide hybrids |
| topic | Oxadiazole probenecid X-ray diffraction enzyme inhibition molecular modelling |
| url | https://www.tandfonline.com/doi/10.1080/14756366.2022.2078969 |
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