1H and 13C NMR spectral assignments of chalcones bearing pyrazoline–carbothioamide groups. (19th June 2013)

• Record Type: Journal Article
• Authors: Yoon, Hyuk; Ahn, Seunghyun; Park, Mijoo; Kim, Dong‐Wook; Kim, Sang Ho; Koh, Dongsoo; Lim, Yoongho
• Is Part Of: Magnetic resonance in chemistry. Volume 51:Number 8(2013:Aug.)
• Page Start: 500
• Page End: 508
• Publication Date: 2013-06-19
• Subjects: chalcone -- pyrazoline–carbothioamide -- flavonoid -- NMR -- 1H NMR -- 13C NMR; Nuclear magnetic resonance spectroscopy -- Periodicals; Chemistry, Organic -- Periodicals; Magnetic resonance -- Periodicals; 538.36
• DOI: 10.1002/mrc.3971
• Languages: English
• ISSNs: 0749-1581

Abstract

Abstract : Chalcones are known to act on various physiological targets. As a result, structural modifications of chalcones have been studied extensively. Benzochalcones, in which the A‐ring of chalcone is substituted with a naphthalene unit, inhibits breast cancer resistance protein. Chalcones in which the α, β‐unsaturated carbonyl group is switched with a pyrazoline moiety are potent cytotoxic agents against various cancer cell lines, and chalcones with a pyrazoline‐1‐carbothioamide group instead of an α, β‐unsaturated carbonyl group exhibit antimicrobial activities. The present report describes hybrid molecules designed from benzochalcone and pyrazoline–carbothioamide. Methoxylation of plant‐derived polyphenols alters their hydrophobicity, resulting in changes in biological function and intracellular compartmentation. In the current study, 22 novel methoxylated 3‐(naphthalen‐2‐yl)‐ N, 5‐diphenyl‐pyrazoline‐1‐carbothioamide derivatives were prepared. This report provides complete assignments of their 1 H and 13 C NMR data, which can be used to subsequently identify chalcones bearing pyrazoline–carbothioamide groups. Copyright © 2013 John Wiley & Sons, Ltd. Abstract : Because chalcones in which the α, β‐unsaturated carbonyl group is switched with a pyrazoline moiety are potent cytotoxic agents against various cancer cell lines, and chalcones with a pyrazoline‐1‐carbothioamide group instead of an α, β‐unsaturated carbonyl group exhibit antimicrobial activities, hybrid molecules were designed from benzochalcone and pyrazoline–carbothioamide. In the current study, 22 novel methoxylated 3‐(naphthalen‐2‐yl)‐ N, 5‐diphenyl‐pyrazoline‐1‐carbothioamide derivatives were synthesized. This report provides complete assignments of their 1 H and 13 C NMR data, which can be used to subsequently identify chalcones bearing pyrazoline–carbothioamide groups.