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N-[2-(5,5-Dimethyl-1,3-dioxane-2-yl)ethyl]amino acids: Their synthesis, anti-inflammatory evaluation and QSAR analysis
Li, Xiangmin2; Zhao, Ming3; Tang, Yu-Rong1; Wang, Chao2; Zhang, Ziding1; Peng, Shiqi3
关键词anti-inflammatory drug chemical synthesis amino acid 1,3-dioxane QSAR
刊名EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
2008
DOI10.1016/j.ejmech.2007.03.015
43期:1页:8-18
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Medicinal
研究领域[WOS]Pharmacology & Pharmacy
关键词[WOS]INFRARED-SPECTRA ; 3D STRUCTURE ; INFLAMMATION ; CANCER
英文摘要

Developing novel anti-inflammatory drugs is increasingly important in modern pharmaceutical industry. In this work, the reactions of both amino acids and their methylesters with 3-(5,5-dimethyl-1,3-dioxane-2-yl)propanal (2) were performed to either directly provide the goal products N-[2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl]amino acids (4a-s) in 9-65% yields or provide the intermediates N-[2-(5,5-dimethyl-1.3-dioxane-2-yl)ethyl]amino acid methylesters (3a-s) in 78-87% yields. The saponification of 3a-s provided 4a-s in 80-89% yields. Using a xylene-induced ear edema model, the anti-inflammatory activities of these newly synthesized anti-inflammatory agents were evaluated. The results indicated that comparing to the vehicle control 17 out of 4a-s significantly inhibited the development of inflammation in mice (p < 0.01). In particular, eight out of 4a-s exhibited an even higher anti-inflammatory activity than the standard reference drug aspirin (p < 0.05-0.01). A QSAR analysis was performed by use of the molecular descriptors generated from e-dragon software. The predictive accuracy of the established QSAR model implies that it may be promising for screening the new derivatives of 2-position amino acid substituted 1,3-dioxanes as potential anti-inflammatory agents. (C) 2007 Elsevier Masson SAS. All rights reserved.

语种英语
WOS记录号WOS:000253274300002
Citation statistics
Cited Times:29[WOS]   [WOS Record]     [Related Records in WOS]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/66899
Collection北京大学药学院
作者单位1.China Agr Univ, Coll Biol Sci, Beijing 100094, Peoples R China
2.Peking Univ, Coll Pharmaceut Sci, Beijing 100083, Peoples R China
3.Capital Med Univ, Coll Pharmaceut Sci, Beijing 100054, Peoples R China
Recommended Citation
GB/T 7714
Li, Xiangmin,Zhao, Ming,Tang, Yu-Rong,et al. N-[2-(5,5-Dimethyl-1,3-dioxane-2-yl)ethyl]amino acids: Their synthesis, anti-inflammatory evaluation and QSAR analysis[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2008,43(1):8-18.
APA Li, Xiangmin,Zhao, Ming,Tang, Yu-Rong,Wang, Chao,Zhang, Ziding,&Peng, Shiqi.(2008).N-[2-(5,5-Dimethyl-1,3-dioxane-2-yl)ethyl]amino acids: Their synthesis, anti-inflammatory evaluation and QSAR analysis.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,43(1),8-18.
MLA Li, Xiangmin,et al."N-[2-(5,5-Dimethyl-1,3-dioxane-2-yl)ethyl]amino acids: Their synthesis, anti-inflammatory evaluation and QSAR analysis".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 43.1(2008):8-18.
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