Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones
Abstract To find new anti-browning and whitening agents in this study, new series of isopropylquinazolinone derivatives were designed and synthesized. All derivatives were evaluated as possible tyrosinase inhibitors and compound 9q bearing 4-fluorobenzyl moieties at the R position exhibited the best...
| Main Authors: | , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
BMC
2023-06-01
|
| Series: | BMC Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.1186/s13065-023-00978-3 |
| _version_ | 1827917202031902720 |
|---|---|
| author | Arshia Hashemi Milad Noori Navid Dastyafteh Seyed Esmaeil Sadat-Ebrahimi Negin Fazelzadeh Haghighi Katayoun Mehrpour Elahe Sattarinezhad Fatemeh Jalali Zafrei Cambyz Irajie Mohammad Ali Daneshmehr Majid Heydari Bagher Larijani Aida Iraji Mohammad Mahdavi |
| author_facet | Arshia Hashemi Milad Noori Navid Dastyafteh Seyed Esmaeil Sadat-Ebrahimi Negin Fazelzadeh Haghighi Katayoun Mehrpour Elahe Sattarinezhad Fatemeh Jalali Zafrei Cambyz Irajie Mohammad Ali Daneshmehr Majid Heydari Bagher Larijani Aida Iraji Mohammad Mahdavi |
| author_sort | Arshia Hashemi |
| collection | DOAJ |
| description | Abstract To find new anti-browning and whitening agents in this study, new series of isopropylquinazolinone derivatives were designed and synthesized. All derivatives were evaluated as possible tyrosinase inhibitors and compound 9q bearing 4-fluorobenzyl moieties at the R position exhibited the best potencies with an IC50 value of 34.67 ± 3.68 µM. The kinetic evaluations of 9q as the most potent derivatives recorded mix-type inhibition. Compounds 9o and 9q also exhibited potent antioxidant capacity with IC50 values of 38.81 and 40.73 µM, respectively confirming their antioxidant potential. Molecular docking studies of 9q as the most potent derivative were exacuated and it was shown that quinazolinone and acetamide moieties of compound 9q participated in interaction with critical His residues of the binding site. The obtained results demonstrated that the 9q can be considered a suitable pharmacophore to develop potent tyrosinase inhibitors. |
| first_indexed | 2024-03-13T03:24:26Z |
| format | Article |
| id | doaj.art-a24627d932c144e285bc18cb67be1ce7 |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-03-13T03:24:26Z |
| publishDate | 2023-06-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-a24627d932c144e285bc18cb67be1ce72023-06-25T11:07:56ZengBMCBMC Chemistry2661-801X2023-06-0117111110.1186/s13065-023-00978-3Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinonesArshia Hashemi0Milad Noori1Navid Dastyafteh2Seyed Esmaeil Sadat-Ebrahimi3Negin Fazelzadeh Haghighi4Katayoun Mehrpour5Elahe Sattarinezhad6Fatemeh Jalali Zafrei7Cambyz Irajie8Mohammad Ali Daneshmehr9Majid Heydari10Bagher Larijani11Aida Iraji12Mohammad Mahdavi13Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran 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 and Pharmaceutical Sciences Research Center, Tehran University of Medical SciencesMolecular Dermatology Research Center and Department of Dermatology, Shiraz University of Medical SciencesStem Cells Technology Research Center, Shiraz University of Medical SciencesDepartment of Pharmacology, School of Medicine, Shiraz University of Medical SciencesCardiovascular Diseases Research Center, Department of Cardiology, Heshmat Hospital, School of Medicine, Guilan University of Medical SciencesDepartment of Medical Biotechnology, School of Advanced Medical Sciences and Technologies, Shiraz University of Medical SciencesDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical SciencesStudent Research Committee, Shiraz University of Medical SciencesEndocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, 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 SciencesAbstract To find new anti-browning and whitening agents in this study, new series of isopropylquinazolinone derivatives were designed and synthesized. All derivatives were evaluated as possible tyrosinase inhibitors and compound 9q bearing 4-fluorobenzyl moieties at the R position exhibited the best potencies with an IC50 value of 34.67 ± 3.68 µM. The kinetic evaluations of 9q as the most potent derivatives recorded mix-type inhibition. Compounds 9o and 9q also exhibited potent antioxidant capacity with IC50 values of 38.81 and 40.73 µM, respectively confirming their antioxidant potential. Molecular docking studies of 9q as the most potent derivative were exacuated and it was shown that quinazolinone and acetamide moieties of compound 9q participated in interaction with critical His residues of the binding site. The obtained results demonstrated that the 9q can be considered a suitable pharmacophore to develop potent tyrosinase inhibitors.https://doi.org/10.1186/s13065-023-00978-3IsopropylquinazolinoneSynthesiseTyrosinaseEnzyme inhibitionKinetic evaluationIn silico studies |
| spellingShingle | Arshia Hashemi Milad Noori Navid Dastyafteh Seyed Esmaeil Sadat-Ebrahimi Negin Fazelzadeh Haghighi Katayoun Mehrpour Elahe Sattarinezhad Fatemeh Jalali Zafrei Cambyz Irajie Mohammad Ali Daneshmehr Majid Heydari Bagher Larijani Aida Iraji Mohammad Mahdavi Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones BMC Chemistry Isopropylquinazolinone Synthesise Tyrosinase Enzyme inhibition Kinetic evaluation In silico studies |
| title | Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones |
| title_full | Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones |
| title_fullStr | Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones |
| title_full_unstemmed | Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones |
| title_short | Synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones |
| title_sort | synthesis and tyrosinase inhibitory activities of novel isopropylquinazolinones |
| topic | Isopropylquinazolinone Synthesise Tyrosinase Enzyme inhibition Kinetic evaluation In silico studies |
| url | https://doi.org/10.1186/s13065-023-00978-3 |
| work_keys_str_mv | AT arshiahashemi synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT miladnoori synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT naviddastyafteh synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT seyedesmaeilsadatebrahimi synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT neginfazelzadehhaghighi synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT katayounmehrpour synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT elahesattarinezhad synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT fatemehjalalizafrei synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT cambyzirajie synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT mohammadalidaneshmehr synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT majidheydari synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT bagherlarijani synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT aidairaji synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones AT mohammadmahdavi synthesisandtyrosinaseinhibitoryactivitiesofnovelisopropylquinazolinones |