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Vol. 32 No. 3 (2020): Vol 32 Issue 3

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Synthesis and Anti-inflammatory Activity of 2-Methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol) and Its Aminomethyl Derivatives

https://doi.org/10.14233/ajchem.2020.22159
H. Hayun
Laboratory of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Universitas Indonesia, Depok 16424, West Java, Indonesia
https://orcid.org/0000-0002-1495-6228
R.N. Fauzan
Laboratory of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Universitas Indonesia, Depok 16424, West Java, Indonesia
N.T. Wibowo
Laboratory of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Universitas Indonesia, Depok 16424, West Java, Indonesia
A. Asrianingtiyas
Laboratory of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Universitas Indonesia, Depok 16424, West Java, Indonesia
N. Afriliana
Laboratory of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Universitas Indonesia, Depok 16424, West Java, Indonesia
T. Ananda
Laboratory of Pharmaceutical and Medicinal Chemistry, Faculty of Pharmacy, Universitas Indonesia, Depok 16424, West Java, Indonesia

Corresponding Author(s) : H. Hayun

hayun@farmasi.ui.ac.id

Asian Journal of Chemistry, Vol. 32 No. 3 (2020): Vol 32 Issue 3

Abstract

Using heat-induced protein denaturation technique, a series of novel synthesized 1,5-diarylpyrazole compounds, namely 2-methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol (1) and its aminomethyl derivatives (2a-e) were evaluated for their anti-inflammatory potentiality. The structures of the synthesized compounds were elucidated using FTIR, NMR (1H & 13C) and mass spectral data. The study found that the activity of aminomethyl derivatives (2a-e) was higher than that of parent compound 1. In this series, aminomethyl derivatives bearing dimethylamino-methyl, diethylaminomethyl and pyrrolidinomethyl moieties (2a, 2c and 2e, respectively) were more active than diclofenac sodium, which was used as a standard. A study on the structure-activity relationship (SAR) suggested that the activity of aminomethyl moiety of the compound was influenced by its pKa value. Thus, novel compounds act as potential anti-inflammatory agents.

Keywords

1,5-Diarylpyrazole Aminomethyl derivatives Anti-inflammatory activity Protein denaturation
Hayun, H., Fauzan, R., Wibowo, N., Asrianingtiyas, A., Afriliana, N., & Ananda, T. (2020). Synthesis and Anti-inflammatory Activity of 2-Methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol) and Its Aminomethyl Derivatives. Asian Journal of Chemistry, 32(3), 607–611. https://doi.org/10.14233/ajchem.2020.22159
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