Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds

CORC > 武汉物理与数学研究所 > 中国科学院武汉物理与数学研究所 > 2011年以前论文发表（包括2011年）

	Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds
	Li, Fang 1,3; Zhang, Huiting 1,3; Jiang, Ling 1; Zhang, Weinong 1; Nie, Jing 2; Feng, Yuqi 2; Yang, Minghui 1; Liu, Maili 1
刊名	MAGNETIC RESONANCE IN CHEMISTRY
	2007-11-01
卷号	45 期号:11 页码:929-936
关键词	NMR valsartan exchange rate conformational analysis quantum chemistry calculation
英文摘要	Valsartan (1), an antihypertensive drug of the sartan family, and three related compounds, 3-methyl-2-((2'-(1-methyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl) pentanoylamino)butyric acid (2), 3-isopropyl-6-propyl-4-(2'-(1H-tetrazol-5-yl)biphenyl-4-yl-methyl) morpholine-2,5-dione (3), and 3-isopropyl-6-propyl-4-(4'-(1H-tetrazol-5-yl)biphenyl4-ylmethyl) morpholine-2,5-dione (4), were studied by nuclear magnetic resonance (NMR) spectroscopy. Assignment of H-1 and C-13 NMR resonances for the compounds were completed using COSY, HSQC and HMBC techniques. It was found that each of the compounds 1, 2, and 4 had two sets of H-1 and C-13 resonances, suggesting the presence of two conformers in solution. Based on NOESY experiments at different temperatures, thermodynamic parameters of the conformational exchange process were deduced for these compounds. The exchange barrier was found to be 17.9 +/- 0.7, 18.5 +/- 0.8, and 17.7 +/- 0.6 kcal mol(-1) with the corresponding free energy difference (Delta G) of 0.32 +/- 0.04, 0.23 +/- 0.01, and 0.13 +/- 0.04 kcal mol(-1) for 1, 2, and 4, respectively, at 298 K. Two conformations of valsartan were elucidated by NMR spectroscopy and quantum chemistry calculation. The results showed that two conformers of valsartan interchange via rotation about the C(O)-N bond. Copyright (c) 2007 John Wiley & Sons, Ltd.
WOS标题词	Science & Technology ; Physical Sciences ; Technology
类目[WOS]	Chemistry, Multidisciplinary ; Chemistry, Physical ; Spectroscopy
研究领域[WOS]	Chemistry ; Spectroscopy
关键词[WOS]	II-RECEPTOR ANTAGONISTS ; MAGNETIC-RESONANCE-SPECTROSCOPY ; ANGIOTENSIN ; LOSARTAN ; HYDROCHLOROTHIAZIDE ; IDENTIFICATION ; HYPERTENSION ; ELUCIDATION ; COMBINATION ; TABLETS
收录类别	SCI
语种	英语
WOS记录号	WOS:000252666900005
公开日期	2015-08-18
内容类型	期刊论文
源URL	[http://ir.wipm.ac.cn/handle/112942/4891]
专题	武汉物理与数学研究所_2011年以前论文发表（包括2011年）
作者单位	1.Chinese Acad Sci, Wuhan Inst Phys & Math, Wuhan Ctr Magnet Resonance, State Key Lab Magnet Resonance & Atom & Mol Phys, Wuhan 430071, Peoples R China 2.Wuhan Univ, Dept Chem, Wuhan 430072, Peoples R China 3.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Li, Fang,Zhang, Huiting,Jiang, Ling,et al. Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds[J]. MAGNETIC RESONANCE IN CHEMISTRY,2007,45(11):929-936.
APA	Li, Fang.,Zhang, Huiting.,Jiang, Ling.,Zhang, Weinong.,Nie, Jing.,...&Liu, Maili.(2007).Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds.MAGNETIC RESONANCE IN CHEMISTRY,45(11),929-936.
MLA	Li, Fang,et al."Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds".MAGNETIC RESONANCE IN CHEMISTRY 45.11(2007):929-936.