Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

doi:10.6023/cjoc201204001

科研成果详情

题名	Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues
其他题名	Synthesis, Crystal Structure, Antioxidant Activity ofChalcones and Its Spiro-heterocyclic Analogues
作者	Wu, Jianzhang1,2; Li, Wulan3; Chen, Lingzi 2; Chu, Shenghui2; Zhao, Chenguang 1; Wei, Tao2; Yang, Shulin 1; Li, Xiaokun1,2
发表日期	2012-11
发表期刊	CHINESE JOURNAL OF ORGANIC CHEMISTRY 影响因子和分区
语种	中文
原始文献类型	Article
关键词	chalcones spiro-heterocyclic synthesis DPPH antioxidant activities crystal structure
其他关键词	STEREOSELECTIVE-SYNTHESIS ; DERIVATIVES ; DISCOVERY
摘要	To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity. Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by H-1 NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured, and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of B1 was monoclinic system, space group C2/c, with cell dimensions of a=21.350(3) angstrom, b=8.6256(10) angstrom, c=26.161(3) angstrom. Spiro-heterocyclic B is the new structure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis of spiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidant activities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strong activity of scavenging DPPH free radicals, were screened. In the 2 types of chalcones analogs, the compounds with 3,4-(OH)(2) in a ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have good antioxidant activities.
其他摘要	To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity.Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by ~1H NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured,and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of B1 was monoclinic system,space group C2/c, with cell dimensions of a=21.350(3) A, b=8.6256(10) A, c=26.161(3) A. Spiro-heterocyclic B is the newstructure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis ofspiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidantactivities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strongactivity of scavenging DPPH free radicals, were screened. In the 2 types of chalcones analogs, the compounds with 3,4-(OH)2in “a” ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have goodantioxidant activities.
资助项目	Technology Foundation for Medical Science of Zhejiang Province [2012KYA129]; Project of Wenzhou Sci Tech Bureau [20090101]; Technology Foundation for Chinese Medicine of Zhejiang Province [2012ZB102]
出版者	SCIENCE PRESS
出版地	BEIJING
ISSN	0253-2786
卷号	32 期号:11 页码:2141-2147
DOI	10.6023/cjoc201204001
页数	7
WOS类目	Chemistry, Organic
WOS研究方向	Chemistry
WOS记录号	WOS:000312684100016
收录类别	SCIE ; SCOPUS ; CSCD ; 万方 ; PKU ; 北大核心 ; ISTIC ; SCI
学科领域	化学工业
URL	查看原文
CSCD记录号	CSCD:4719230
SCOPUSEID	2-s2.0-84874617934
通讯作者地址	[Wu, Jianzhang]Institute of Biotechnology,Nanjing University of Science and Technology,China
Scopus学科分类	Organic Chemistry
引用统计	被引频次：6[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	https://kms.wmu.edu.cn/handle/3ETUA0LF/3359
专题	药学院（分析测试中心）第一临床医学院（信息与工程学院）、附属第一医院_计算机与信息管理系
通讯作者	Wu, Jianzhang
作者单位	1.Institute of Biotechnology,Nanjing University of Science and Technology,China; 2.School of Pharmacy,Wenzhou Medical College,China; 3.College of Information Science and Computer Engineering,Wenzhou Medical College,China
第一作者单位	温州医科大学
推荐引用方式 GB/T 7714	Wu, Jianzhang,Li, Wulan,Chen, Lingzi,et al. Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2012,32(11):2141-2147.
APA	Wu, Jianzhang., Li, Wulan., Chen, Lingzi., Chu, Shenghui., Zhao, Chenguang., ... & Li, Xiaokun. (2012). Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 32(11), 2141-2147.
MLA	Wu, Jianzhang,et al."Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues".CHINESE JOURNAL OF ORGANIC CHEMISTRY 32.11(2012):2141-2147.

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