Synthesis, molecular docking study, and in vivo biological evaluation of pyrazolopyridines derived from monocarbonyl curcumin analogues as potential anti-inflammatory agents

Authors

  • Enda Mora Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia & Universitas Riau, Pekanbaru, Riau, Indonesia
  • Hilwan Yuda Teruna Universitas Riau, Pekanbaru, Riau, Indonesia https://orcid.org/0000-0001-6363-5239
  • Neni Frimayanti Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia
  • Ihsan Ikhtiarudin Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia
  • Noval Herfindo Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia https://orcid.org/0000-0003-4939-0348
  • Adel Zamri Universitas Riau, Pekanbaru, Riau, Indonesia

DOI:

https://doi.org/10.46542/pe.2023.232.200206

Keywords:

Anti-inflammatory, Docking, In vivo, Pyrazolopyridine, Synthesis

Abstract

Background: Pyrazolopyridines are heterocyclic compounds with nitrogen atoms in the ring, and they have been used as one of the important pharmacophores in drug design. Pyrazole derivatives have been synthesised and applied in the pharmaceutical industry as active drugs. The recent commercial success of pyrazole COX-2 inhibitors has brought even more attention to the significance of this heterocyclic ring in medicinal chemistry.

Objective: This study aimed to synthesise new compounds as anti-inflammatory candidates from the pyrazolopyridine group.

Method: Synthesis was carried out using the Claisen-Schmidt reaction through condensation of substituted benzaldehyde and 4-piperidone to produce mono-ketone curcumin analogues, which were then cyclised with phenylhydrazine. The results of the synthesis were characterised using FT-IR, 1H-NMR, and MS. Docking analysis was performed on the 3LN1 protein with MOE 2021.0901. Furthermore, an in vivo anti-inflammatory test was applied using a plethysmometer.

Results: The synthesis results obtained two pyrazolopyridine compounds, and the docking results showed that both of these synthesised compounds could interact with the COX-2 receptor binding site.

Conclusion: Compound 2 demonstrated good anti-inflammatory activities. This strategy is in the preliminary stages of identifying novel substances that may be used as anti-inflammatory agents in the future.

Author Biographies

Enda Mora, Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia & Universitas Riau, Pekanbaru, Riau, Indonesia

Department of Pharmacy & Department of Chemistry, Faculty of Mathematics and Sciences

Hilwan Yuda Teruna, Universitas Riau, Pekanbaru, Riau, Indonesia

Department of Chemistry, Faculty of Mathematics and Sciences

Neni Frimayanti , Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia

Department of Pharmacy

Ihsan Ikhtiarudin, Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia

Department of Pharmacy

Noval Herfindo, Sekolah Tinggi Ilmu Farmasi Riau, Pekanbaru, Riau, Indonesia

Department of Pharmacy

Adel Zamri, Universitas Riau, Pekanbaru, Riau, Indonesia

Department of Chemistry, Faculty of Mathematics and Sciences

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Published

15-05-2023

How to Cite

Mora, E., Teruna, H. Y., Frimayanti , N., Ikhtiarudin, I., Herfindo, N., & Zamri, A. (2023). Synthesis, molecular docking study, and in vivo biological evaluation of pyrazolopyridines derived from monocarbonyl curcumin analogues as potential anti-inflammatory agents. Pharmacy Education, 23(2), p. 200–206. https://doi.org/10.46542/pe.2023.232.200206

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