Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine
The tyrosinase enzyme plays an essential role in the pigmentation of human skin, fruits, and vegetables. It has been tied with several human skin diseases and post-harvest problems. Hence, the tyrosinase enzyme becomes an excellent therapeutic target to overcome these issues. This study aimed to scr...
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| Format: | Article |
| Language: | English |
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Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University
2022-05-01
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| Series: | Jurnal Kimia Sains dan Aplikasi |
| Subjects: | |
| Online Access: | https://ejournal.undip.ac.id/index.php/ksa/article/view/42713 |
| _version_ | 1797862271307743232 |
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| author | Nelly Oscifiani Noval Herfindo Rahayu Rahayu Neni Frimayanti Adel Zamri |
| author_facet | Nelly Oscifiani Noval Herfindo Rahayu Rahayu Neni Frimayanti Adel Zamri |
| author_sort | Nelly Oscifiani |
| collection | DOAJ |
| description | The tyrosinase enzyme plays an essential role in the pigmentation of human skin, fruits, and vegetables. It has been tied with several human skin diseases and post-harvest problems. Hence, the tyrosinase enzyme becomes an excellent therapeutic target to overcome these issues. This study aimed to screen tyrosinase inhibitors by synthesizing halogen-substituted pyrazolopyridine derivatives. The pyrazolopyridine compound was obtained through two stages of synthesis. First, the intermediate compound, a derivative of 3,5-bis(arylidene)-4-piperidone, was synthesized through the Cleisen-Schmidt condensation reaction of 4-piperidone and benzaldehyde derivatives. Furthermore, the intermediate compound was reacted with phenylhydrazine through a cyclocondensation reaction to produce the titled compound with an 11% yield. The chemical structure of the target compound was identified through the interpretation of UV, FTIR, NMR, and HRMS spectra. Then an in vitro assay was conducted on the tyrosinase enzyme of the fungus Agaricus bisporus by detecting the presence of dopachrome at a wavelength of 492 nm. As a result, the in vitro assay showed that the titled compound had a weak inhibitory activity, and the IC50 value was > 500 µM. Thus, the synthesized compound is considered inactive. |
| first_indexed | 2024-04-09T22:16:32Z |
| format | Article |
| id | doaj.art-c0b1e1d905bb4743abd0d042eb0bef08 |
| institution | Directory Open Access Journal |
| issn | 1410-8917 2597-9914 |
| language | English |
| last_indexed | 2024-04-09T22:16:32Z |
| publishDate | 2022-05-01 |
| publisher | Chemistry Department, Faculty of Sciences and Mathematics, Diponegoro University |
| record_format | Article |
| series | Jurnal Kimia Sains dan Aplikasi |
| spelling | doaj.art-c0b1e1d905bb4743abd0d042eb0bef082023-03-23T03:32:45ZengChemistry Department, Faculty of Sciences and Mathematics, Diponegoro UniversityJurnal Kimia Sains dan Aplikasi1410-89172597-99142022-05-0125518519110.14710/jksa.25.5.185-19120553Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]PyridineNelly Oscifiani0Noval Herfindo1https://orcid.org/0000-0003-4939-0348Rahayu Rahayu2Neni Frimayanti3Adel Zamri4https://orcid.org/0000-0003-4066-877XDepartment of Chemistry, University of Riau, Pekanbaru, Riau, IndonesiaSekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, IndonesiaDepartment of Chemistry, University of Riau, Pekanbaru, Riau, IndonesiaSekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, IndonesiaDepartment of Chemistry, University of Riau, Pekanbaru, Riau, IndonesiaThe tyrosinase enzyme plays an essential role in the pigmentation of human skin, fruits, and vegetables. It has been tied with several human skin diseases and post-harvest problems. Hence, the tyrosinase enzyme becomes an excellent therapeutic target to overcome these issues. This study aimed to screen tyrosinase inhibitors by synthesizing halogen-substituted pyrazolopyridine derivatives. The pyrazolopyridine compound was obtained through two stages of synthesis. First, the intermediate compound, a derivative of 3,5-bis(arylidene)-4-piperidone, was synthesized through the Cleisen-Schmidt condensation reaction of 4-piperidone and benzaldehyde derivatives. Furthermore, the intermediate compound was reacted with phenylhydrazine through a cyclocondensation reaction to produce the titled compound with an 11% yield. The chemical structure of the target compound was identified through the interpretation of UV, FTIR, NMR, and HRMS spectra. Then an in vitro assay was conducted on the tyrosinase enzyme of the fungus Agaricus bisporus by detecting the presence of dopachrome at a wavelength of 492 nm. As a result, the in vitro assay showed that the titled compound had a weak inhibitory activity, and the IC50 value was > 500 µM. Thus, the synthesized compound is considered inactive.https://ejournal.undip.ac.id/index.php/ksa/article/view/42713tyrosinaseinhibitor tyrosinasepirazolo[4,3c]piridin. |
| spellingShingle | Nelly Oscifiani Noval Herfindo Rahayu Rahayu Neni Frimayanti Adel Zamri Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine Jurnal Kimia Sains dan Aplikasi tyrosinase inhibitor tyrosinase pirazolo[4,3c]piridin. |
| title | Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine |
| title_full | Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine |
| title_fullStr | Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine |
| title_full_unstemmed | Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine |
| title_short | Synthesis and Tyrosinase Inhibitory Activity of (E)-5-Benzyl-7- (3-Bromobenzylidene)-3-(3-Bromophenyl)-2-Phenyl-3,3a, 4,5,6,7-Hexahydro-2H-Pyrazolo[4,3-c]Pyridine |
| title_sort | synthesis and tyrosinase inhibitory activity of e 5 benzyl 7 3 bromobenzylidene 3 3 bromophenyl 2 phenyl 3 3a 4 5 6 7 hexahydro 2h pyrazolo 4 3 c pyridine |
| topic | tyrosinase inhibitor tyrosinase pirazolo[4,3c]piridin. |
| url | https://ejournal.undip.ac.id/index.php/ksa/article/view/42713 |
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