Hyeryoung Jung, Seunghyun Ahn, Yearam Jung
Mar 1, 2016
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Journal
Magnetic Resonance in Chemistry
Abstract
Chalcones are secondary metabolites in plants produced via the phenylpropanoid pathway. Because 2-hydroxychalcones (Fig. 1A) are known to show various biological activities including anticancer and antioxidative effects, their derivatives have been investigated and reported. However, cyclization of 2hydroxychalcones results in the formation of flavanones. As such, the α,β-unsaturated carbonyl group was replaced with a pyrazoline group (Fig. 1B). Diphenylpyrazolines contain a C6-C3-C6 skeleton similar to chalcones, and they show more biological activities including tyrosinase inhibition, antimicrobial effects, and monoamine oxidase inhibition. Diphenylpyrazolinyl-1-carbothioamdes (Fig. 1C) show dual inhibitory effects on monoamine oxidase and cholinesterase. Therefore, we designed phenyl-N-phenyl-naphthalenylpyrazolinyl-1-carbothioamide (Fig. 1D) and synthesized 19 derivatives. Pyrazolinyl-1-carbothioamdes are important because of their diverse biological activities, and their NMR and mass spectrometric (MS) data can aid in the identification of newly synthesized or isolated derivatives in the future. Therefore, we report herein the complete H and C NMR and highresolution MS data of 19 novel polymethoxylated diphenylnaphthylpyrazolinyl-1-carbothioamides.