Synthesis and multifaceted exploration of 4-phenylpiperidin-4-ol substituted pyrazole: photophysical insights with biological activity

• Autorzy: Al-Hazmi Ghaferah H. , Marrakkur Vidyagayatri , Naik Lohit , Refat Moamen S.

Identyfikatory

DOI

10.2478/pjct-2024-0023

• Języki publikacji: EN

Abstrakty

EN

In this study, we successfully synthesized a pyrazole derivative, specifi cally 4-phenylpiperidin-4-ol substituted pyrazole (CHP), through the reaction of Grignard reagents in combination with pyrazole. This newly synthesized molecule was subjected to a comprehensive evaluation for both its photophysical and biological applications. Notably, CHP exhibited promising invitro antifungal and antibacterial activities, primarily attributed to the presence of the 4-phenylpiperidin-4-ol moiety and resulting component contributed to an enhanced absorption rate of lipids, thereby improving the pharmacological activity of CHP. This correlation between structure and function was further supported by the outcomes of structure-activity relationship studies. Additionally, we conducted in silico studies to examine the molecular interactions of the synthesized molecule with key proteins, including DNA Gyrase, Lanosterol 14 α-demethylase, and KEAP1-NRF2. The results unveiled robust binding interactions at specific sites within these proteins, indicating potential therapeutic relevance. Furthermore, the photophysical properties of the synthesized compounds were thoroughly investigated using the ab-initio technique. This involved the determination of ground state optimization and HOMO-LUMO energy levels, all calculated with the DFT-B3LYP-6-31G(d) basis set. The assessment of the theoretically estimated HOMO-LUMO value provided insights into the global chemical reactivity descriptors, revealing that the synthesized molecule boasts a highly electronegative and electrophilic index. Taken together, our findings suggest that pyrazole derivatives with 4-phenylpiperidin-4-ol substitutions exhibit promising applications in both photophysical and biological contexts.

Słowa kluczowe

EN

pyrazolones; in-vitro biological activity; in-silico biological activity; HOMO-LUMO; Highest Occupied Molecular Orbital

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2024
• Tom: Vol. 26, nr 3
• Strony: 1--7
• Opis fizyczny: Bibliogr. 28 poz., rys., tab., wz.

Twórcy

autor

Al-Hazmi Ghaferah H.

• Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi Arabia

autor

Marrakkur Vidyagayatri

• Department of Chemistry, NMKRV College for Women, Bengaluru-560006, India

autor

Naik Lohit

• Department of Physics and Electronics, CHRIST (Deemed to be University), Bengaluru-560029, India

autor

Refat Moamen S.

• Department of Chemistry, College of Science, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia

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