Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors
Abstract In this study, 18 novel quinoline-based-benzo[d]imidazole derivatives were synthesized and screened for their α-glucosidase inhibitory potential. All compounds in the series except 9q showed a significant α-glucosidase inhibition with IC50 values in the range of 3.2 ± 0.3–185.0 ± 0.3 µM, as...
| Main Authors: | , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2022-08-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-022-18455-7 |
| _version_ | 1798038988444925952 |
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| author | Milad Noori Ali Davoodi Aida Iraji Navid Dastyafteh Minoo Khalili Mehdi Asadi Maryam Mohammadi Khanaposhtani Somayeh Mojtabavi Mehdi Dianatpour Mohammad Ali Faramarzi Bagher Larijani Massoud Amanlou Mohammad Mahdavi |
| author_facet | Milad Noori Ali Davoodi Aida Iraji Navid Dastyafteh Minoo Khalili Mehdi Asadi Maryam Mohammadi Khanaposhtani Somayeh Mojtabavi Mehdi Dianatpour Mohammad Ali Faramarzi Bagher Larijani Massoud Amanlou Mohammad Mahdavi |
| author_sort | Milad Noori |
| collection | DOAJ |
| description | Abstract In this study, 18 novel quinoline-based-benzo[d]imidazole derivatives were synthesized and screened for their α-glucosidase inhibitory potential. All compounds in the series except 9q showed a significant α-glucosidase inhibition with IC50 values in the range of 3.2 ± 0.3–185.0 ± 0.3 µM, as compared to the standard drug acarbose (IC50 = 750.0 ± 5.0 µM). A kinetic study indicated that compound 9d as the most potent derivative against α-glucosidase was a competitive type inhibitor. Furthermore, the molecular docking study revealed the effective binding interactions of 9d with the active site of the α-glucosidase enzyme. The results indicate that the designed compounds have the potential to be further studied as new anti-diabetic agents. |
| first_indexed | 2024-04-11T21:47:44Z |
| format | Article |
| id | doaj.art-4cf577f26bc7424996e47b7050a16d03 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-04-11T21:47:44Z |
| publishDate | 2022-08-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-4cf577f26bc7424996e47b7050a16d032022-12-22T04:01:22ZengNature PortfolioScientific Reports2045-23222022-08-0112111310.1038/s41598-022-18455-7Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitorsMilad Noori0Ali Davoodi1Aida Iraji2Navid Dastyafteh3Minoo Khalili4Mehdi Asadi5Maryam Mohammadi Khanaposhtani6Somayeh Mojtabavi7Mehdi Dianatpour8Mohammad Ali Faramarzi9Bagher Larijani10Massoud Amanlou11Mohammad Mahdavi12Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical SciencesStem Cells Technology Research Center, Shiraz University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical SciencesCellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical SciencesDepartment of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical SciencesStem Cells Technology Research Center, Shiraz University of Medical SciencesDepartment of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesDepartment of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical SciencesAbstract In this study, 18 novel quinoline-based-benzo[d]imidazole derivatives were synthesized and screened for their α-glucosidase inhibitory potential. All compounds in the series except 9q showed a significant α-glucosidase inhibition with IC50 values in the range of 3.2 ± 0.3–185.0 ± 0.3 µM, as compared to the standard drug acarbose (IC50 = 750.0 ± 5.0 µM). A kinetic study indicated that compound 9d as the most potent derivative against α-glucosidase was a competitive type inhibitor. Furthermore, the molecular docking study revealed the effective binding interactions of 9d with the active site of the α-glucosidase enzyme. The results indicate that the designed compounds have the potential to be further studied as new anti-diabetic agents.https://doi.org/10.1038/s41598-022-18455-7 |
| spellingShingle | Milad Noori Ali Davoodi Aida Iraji Navid Dastyafteh Minoo Khalili Mehdi Asadi Maryam Mohammadi Khanaposhtani Somayeh Mojtabavi Mehdi Dianatpour Mohammad Ali Faramarzi Bagher Larijani Massoud Amanlou Mohammad Mahdavi Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors Scientific Reports |
| title | Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors |
| title_full | Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors |
| title_fullStr | Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors |
| title_full_unstemmed | Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors |
| title_short | Design, synthesis, and in silico studies of quinoline-based-benzo[d]imidazole bearing different acetamide derivatives as potent α-glucosidase inhibitors |
| title_sort | design synthesis and in silico studies of quinoline based benzo d imidazole bearing different acetamide derivatives as potent α glucosidase inhibitors |
| url | https://doi.org/10.1038/s41598-022-18455-7 |
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