TY - JOUR
T1 - Synthesis and anti-inflammatory activity of 2-methoxy-4-(1-phenyl-3-methyl-1H-pyrazol-5-yl)phenol) and its aminomethyl derivatives
AU - Hayun, H.
AU - Fauzan, R. N.
AU - Wibowo, N. T.
AU - Asrianingtiyas, A.
AU - Afriliana, N.
AU - Ananda, T.
N1 - Funding Information:
The authors thank The Directorate of Research and Community Services, Universitas Indonesia, Depok, Indonesia for providing the financial support via PITTA Grant 2018. Thanks are also due to Department of Chemistry, Institut Teknologi Bandung (ITB), Bandung, Indonesia for recording NMR and mass spectra.
Publisher Copyright:
© 2020 Chemical Publishing Co.. All rights reserved.
PY - 2020/1/1
Y1 - 2020/1/1
N2 - 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.
AB - 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.
KW - 1,5-Diarylpyrazole
KW - Aminomethyl derivatives
KW - Anti-inflammatory activity
KW - Protein denaturation
UR - http://www.scopus.com/inward/record.url?scp=85078782396&partnerID=8YFLogxK
U2 - 10.14233/ajchem.2020.22159
DO - 10.14233/ajchem.2020.22159
M3 - Article
AN - SCOPUS:85078782396
VL - 32
SP - 607
EP - 611
JO - Asian Journal of Chemistry
JF - Asian Journal of Chemistry
SN - 0970-7077
IS - 3
ER -