4-[(3,4-Dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1<em>H</em>-pyrazol-4-yl)-2,4-dihydro-3<em>H</em>-1,2,4-triazole-3-thione

• Main Authors: Soukhyarani Gopal Nayak, Boja Poojary
• Format: Article
• Language: English
• Published: MDPI AG 2019-03-01
• Series: Molbank
• Subjects: 1,2,4-triazole-3-thione; molecular docking; prostaglandin reductase
• Online Access: https://www.mdpi.com/1422-8599/2019/1/M1055

4-Amino-5-(5-methyl-1-phenyl-1<i>H</i>-pyrazol-4-yl)-2,4-dihydro-3<i>H</i>-1,2,4-triazole-3-thione (<b>1</b>) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1<i>H</i>-pyrazol-4-yl)-2,4-dihydro-3<i>H</i>-1,2,4-triazole-3-thione (<b>2</b>) in 80% yield. The obtained solid product was recrystallized from ethanol. The compound was characterized by elemental analyses, mass spectrometry, FT-IR, ¹H and ¹³C-NMR spectroscopy. To study the binding interactions of the compound with receptor, it was docked with the human prostaglandin reductase (PTGR2). The docking pose and noncovalent interactions gave insights into its plausible inhibitory action.