Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes
This study focuses on the synthesis, characterisation, and bioactivity evaluation of four imines derived from the condensation of 4-aminoantipyrine with different phenolic aldehydes: 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, and 4-hydroxy-3-methoxybenzaldehyde. These c...
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Croatian Society of Chemical Engineers
2025-01-01
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| Series: | Kemija u Industriji |
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| Online Access: | http://silverstripe.fkit.hr/kui/assets/Uploads/2-7-16-KUI-1-2-2025.pdf |
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| author | Muamer Dizdar Anela Topčagić Monia Avdić Danijela Vidic Milka Maksimović |
| author_facet | Muamer Dizdar Anela Topčagić Monia Avdić Danijela Vidic Milka Maksimović |
| author_sort | Muamer Dizdar |
| collection | DOAJ |
| description | This study focuses on the synthesis, characterisation, and bioactivity evaluation of four imines derived from the condensation of 4-aminoantipyrine with different phenolic aldehydes: 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, and 4-hydroxy-3-methoxybenzaldehyde. These compounds were synthesised to explore their potential in various biological activities, including antioxidant, acetylcholinesterase (AChE) inhibitory, and antibacterial activities. Characterisation of these imines by IR, 1H and 13C NMR, HR-ESI-MS, and elemental analysis confirmed their proposed structures. The antioxidant activity of the synthesised compounds was assessed using five different methods, with the imine derived from 3,4-dihydroxybenzaldehyde displaying the highest antioxidant activity, attributed to its catechol arrangement of phenolic groups. Additionally, the AChE-inhibitory activity of these compounds was investigated, revealing that the degree of hydroxylation and the introduction of a methoxy group significantly influenced their inhibitory efficacy. Molecular docking studies highlighted the main interactions between the imines and AChE, identifying the most energetically favourable binding sites. Antibacterial testing against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli indicated that all compounds exhibited broad antibacterial activities. This comprehensive analysis demonstrates the significant potential of these synthesised imines as bioactive molecules, offering insights into how structural modifications can enhance their biological functions. |
| format | Article |
| id | doaj-art-0c891acd3cef4d3b82d7e75af243079e |
| institution | Kabale University |
| issn | 0022-9830 1334-9090 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Croatian Society of Chemical Engineers |
| record_format | Article |
| series | Kemija u Industriji |
| spelling | doaj-art-0c891acd3cef4d3b82d7e75af243079e2025-01-16T13:46:06ZengCroatian Society of Chemical EngineersKemija u Industriji0022-98301334-90902025-01-01741-271610.15255/KUI.2024.013Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic AldehydesMuamer Dizdar0Anela Topčagić1Monia Avdić2Danijela Vidic3Milka Maksimović4Faculty of Science, University of Sarajevo, Zmaja od Bosne 33–35, 71 000 Sarajevo, Bosnia and HerzegovinaFaculty of Science, University of Sarajevo, Zmaja od Bosne 33–35, 71 000 Sarajevo, Bosnia and HerzegovinaDepartment of Genetics and Bioengineering, International Burch University, Francuske revolucije bb, 71 210 Ilidža, Bosnia and HerzegovinaFaculty of Science, University of Sarajevo, Zmaja od Bosne 33–35, 71 000 Sarajevo, Bosnia and HerzegovinaFaculty of Science, University of Sarajevo, Zmaja od Bosne 33–35, 71 000 Sarajevo, Bosnia and HerzegovinaThis study focuses on the synthesis, characterisation, and bioactivity evaluation of four imines derived from the condensation of 4-aminoantipyrine with different phenolic aldehydes: 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, and 4-hydroxy-3-methoxybenzaldehyde. These compounds were synthesised to explore their potential in various biological activities, including antioxidant, acetylcholinesterase (AChE) inhibitory, and antibacterial activities. Characterisation of these imines by IR, 1H and 13C NMR, HR-ESI-MS, and elemental analysis confirmed their proposed structures. The antioxidant activity of the synthesised compounds was assessed using five different methods, with the imine derived from 3,4-dihydroxybenzaldehyde displaying the highest antioxidant activity, attributed to its catechol arrangement of phenolic groups. Additionally, the AChE-inhibitory activity of these compounds was investigated, revealing that the degree of hydroxylation and the introduction of a methoxy group significantly influenced their inhibitory efficacy. Molecular docking studies highlighted the main interactions between the imines and AChE, identifying the most energetically favourable binding sites. Antibacterial testing against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli indicated that all compounds exhibited broad antibacterial activities. This comprehensive analysis demonstrates the significant potential of these synthesised imines as bioactive molecules, offering insights into how structural modifications can enhance their biological functions.http://silverstripe.fkit.hr/kui/assets/Uploads/2-7-16-KUI-1-2-2025.pdfsynthesis1h-pyrazol-3(2h)-onephenolic aldehydesin vitro bioactivityin silico study |
| spellingShingle | Muamer Dizdar Anela Topčagić Monia Avdić Danijela Vidic Milka Maksimović Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes Kemija u Industriji synthesis 1h-pyrazol-3(2h)-one phenolic aldehydes in vitro bioactivity in silico study |
| title | Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes |
| title_full | Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes |
| title_fullStr | Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes |
| title_full_unstemmed | Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes |
| title_short | Synthesis and Structural Insight into the Bioactivity of Imines with 1,5-Dimethyl-2-Phenyl-1H-Pyrazol-3(2H)-One Structural Unit Derived from Phenolic Aldehydes |
| title_sort | synthesis and structural insight into the bioactivity of imines with 1 5 dimethyl 2 phenyl 1h pyrazol 3 2h one structural unit derived from phenolic aldehydes |
| topic | synthesis 1h-pyrazol-3(2h)-one phenolic aldehydes in vitro bioactivity in silico study |
| url | http://silverstripe.fkit.hr/kui/assets/Uploads/2-7-16-KUI-1-2-2025.pdf |
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