Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units

In this study, a series of 3-phenylpropanamide derivatives with acyl hydrazone units were synthesized and characterized by 1H NMR, 13C NMR and HR MS. And the structure of compound III33 was confirmed by X-ray single crystal. The bioassay results showed that, compounds III8, III17, III22, and III34 s...

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Autores principales:	Liyun Yang, Min Zhang, Qin Liu, Kun Wei, Zhuo Chen, Weiming Xu
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Phenylpropanamide derivatives Antibacterial activities Antifungal activities Acyl hydrazone X-ray single crystal Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/57302dbf2e0847679a274b3d3c8a03db
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spelling	oai:doaj.org-article:57302dbf2e0847679a274b3d3c8a03db2021-11-26T04:24:37ZDesign, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units1319-610310.1016/j.jscs.2021.101389https://doaj.org/article/57302dbf2e0847679a274b3d3c8a03db2021-12-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S1319610321001940https://doaj.org/toc/1319-6103In this study, a series of 3-phenylpropanamide derivatives with acyl hydrazone units were synthesized and characterized by 1H NMR, 13C NMR and HR MS. And the structure of compound III33 was confirmed by X-ray single crystal. The bioassay results showed that, compounds III8, III17, III22, and III34 showed excellent inhibition on Xanthomonas oryzae pv. pryzae (Xoo) with EC50 values of 7.1, 8.8, 9.5, and 4.7 μg/mL in vitro. The EC50 values of compounds III12, III14 and III33 against Ralstonia solanacearum (Rs) were 7.6, 7.6 and 7.9 μg/mL, respectively, all lower than the values of thiadiazol copper (TC) was 66.8 μg/mL and bismerthiazol (BT) was 72.4 μg/mL. Compounds III12, III14, III33, and III34 exhibited excellent antibacterial activity of more than 80% against Xanthomonas axonopodis pv. citri (Xac) in vitro. Besides, compounds III8 (51.4%) and III34 (52.1%) were highly effective against Xoo in vivo, outperforming TC (49.5%) and BT (47.8%). Compounds III8 (29.8%) and III34 (24.6%) were close to TC (41.7%) and BT (47.8%) in terms of protective efficacy against Xoo in vivo. Meanwhile, some of title compounds also displayed inhibitory effects against phytopathogenic fungi. In a word, this study illustrated that the structures combined with phenylpropane amide derivatives of the acyl hydrazone units could be used as potential antibacterial reagents in the future.Liyun YangMin ZhangQin LiuKun WeiZhuo ChenWeiming XuElsevierarticlePhenylpropanamide derivativesAntibacterial activitiesAntifungal activitiesAcyl hydrazoneX-ray single crystalChemistryQD1-999ENJournal of Saudi Chemical Society, Vol 25, Iss 12, Pp 101389- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Phenylpropanamide derivatives Antibacterial activities Antifungal activities Acyl hydrazone X-ray single crystal Chemistry QD1-999
spellingShingle	Phenylpropanamide derivatives Antibacterial activities Antifungal activities Acyl hydrazone X-ray single crystal Chemistry QD1-999 Liyun Yang Min Zhang Qin Liu Kun Wei Zhuo Chen Weiming Xu Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
description	In this study, a series of 3-phenylpropanamide derivatives with acyl hydrazone units were synthesized and characterized by 1H NMR, 13C NMR and HR MS. And the structure of compound III33 was confirmed by X-ray single crystal. The bioassay results showed that, compounds III8, III17, III22, and III34 showed excellent inhibition on Xanthomonas oryzae pv. pryzae (Xoo) with EC50 values of 7.1, 8.8, 9.5, and 4.7 μg/mL in vitro. The EC50 values of compounds III12, III14 and III33 against Ralstonia solanacearum (Rs) were 7.6, 7.6 and 7.9 μg/mL, respectively, all lower than the values of thiadiazol copper (TC) was 66.8 μg/mL and bismerthiazol (BT) was 72.4 μg/mL. Compounds III12, III14, III33, and III34 exhibited excellent antibacterial activity of more than 80% against Xanthomonas axonopodis pv. citri (Xac) in vitro. Besides, compounds III8 (51.4%) and III34 (52.1%) were highly effective against Xoo in vivo, outperforming TC (49.5%) and BT (47.8%). Compounds III8 (29.8%) and III34 (24.6%) were close to TC (41.7%) and BT (47.8%) in terms of protective efficacy against Xoo in vivo. Meanwhile, some of title compounds also displayed inhibitory effects against phytopathogenic fungi. In a word, this study illustrated that the structures combined with phenylpropane amide derivatives of the acyl hydrazone units could be used as potential antibacterial reagents in the future.
format	article
author	Liyun Yang Min Zhang Qin Liu Kun Wei Zhuo Chen Weiming Xu
author_facet	Liyun Yang Min Zhang Qin Liu Kun Wei Zhuo Chen Weiming Xu
author_sort	Liyun Yang
title	Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
title_short	Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
title_full	Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
title_fullStr	Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
title_full_unstemmed	Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
title_sort	design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/57302dbf2e0847679a274b3d3c8a03db
work_keys_str_mv	AT liyunyang designsynthesisandbiologicalevaluationofnovel3phenylpropanamidederivativeswithacylhydrazoneunits AT minzhang designsynthesisandbiologicalevaluationofnovel3phenylpropanamidederivativeswithacylhydrazoneunits AT qinliu designsynthesisandbiologicalevaluationofnovel3phenylpropanamidederivativeswithacylhydrazoneunits AT kunwei designsynthesisandbiologicalevaluationofnovel3phenylpropanamidederivativeswithacylhydrazoneunits AT zhuochen designsynthesisandbiologicalevaluationofnovel3phenylpropanamidederivativeswithacylhydrazoneunits AT weimingxu designsynthesisandbiologicalevaluationofnovel3phenylpropanamidederivativeswithacylhydrazoneunits
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Design, synthesis and biological evaluation of novel 3-phenylpropanamide derivatives with acyl hydrazone units

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