Novel Pyrazole-Linked Pyran Hybrids: Synthesis, Anti-inflammatory Evaluation, Molecular Docking Studies

Abdelmonsef, Aboubakr H.; Abdelreheim, Mohamed; Abdel Rady, Hend S.; Mohamed, Omina A.; Abdelhafiz, Ibrahim Saad; Reffat, Hala M.

doi:10.21608/ejchem.2024.305934.10053

Novel Pyrazole-Linked Pyran Hybrids: Synthesis, Anti-inflammatory Evaluation, Molecular Docking Studies

Document Type : Original Article

Authors

¹ Chemistry Department, Faculty of Science, South Valley University, 83523 Qena, Egypt

² Chemistry Department, Faculty of Science, Arish University

³ Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt

⁴ Department of Biochemistry and Molecular Biology, Theodor Bilharz Research Institute, Giza, Egypt

10.21608/ejchem.2024.305934.10053

Abstract

In this study, a series of novel pyrazole-linked pyran hybrids was synthesized starting from 4-acetyl-1,3-diphenyl-1H-pyrazole-5(4H)-ole 1. Their structures were characterized by means of spectroscopic techniques. Further, their anti-inflammatory activities were in vitro examined using inhibition of protein denaturation, membrane stabilization assay, and quantitative real-time PCR (qRT-PCR). Compound 6 showed observed anti-inflammatory activity compared with diclofenac. Moreover, the molecular docking approach for the newly prepared hybrid molecules was also performed against phosphodiesterase 4 enzyme (PDE4) to investigate their binding modes of action. Remarkably, compound 6 exhibited the lowest binding energy (-10.8 kcal/mol) against the target. Additionally, the predicted ADMET properties of these molecules exhibited favorable drug-likeness properties.

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