Synthesis and anti-inflammatory activity of 2-methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol) and its aminomethyl derivatives

H. Hayun, R. N. Fauzan, N. T. Wibowo, A. Asrianingtiyas, N. Afriliana, T. Ananda

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)607-611
Number of pages5
JournalAsian Journal of Chemistry
Volume32
Issue number3
DOIs
Publication statusPublished - 1 Jan 2020

Keywords

  • 1,5-Diarylpyrazole
  • Aminomethyl derivatives
  • Anti-inflammatory activity
  • Protein denaturation

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