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

Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds. Research Abstract Details 

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Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds. Abstract Text:

Fang Li,Huiting Zhang,Ling Jiang,Weinong Zhang,Jing Nie,Yuqi Feng,Minghui Yang,Maili Liu,Fang Li,Huiting Zhang,Ling Jiang,Weinong Zhang,Jing Nie,Yuqi Feng,Minghui Yang,Maili Liu,

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-ylmethyl) 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 (1)H and (13)C 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 (1)H and (13)C 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 (DeltaG) 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.

Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds. Publishing Authors By Initials

F Li,H Zhang,L Jiang,W Zhang,J Nie,Y Feng,M Yang,M Liu,F Li,H Zhang,L Jiang,W Zhang,J Nie,Y Feng,M Yang,M Liu,

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Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Magnetic resonance in chemistry : MRC

VOLUME: 45

Page Numbers: 929-36

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ISSN: 0749-1581

DAY: 22

MONTH: Nov

YEAR: 2007

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

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LANGUAGE: eng

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Grant and Affiliation Information for Dynamic NMR study and theoretical calculations on the conformational exchange of valsartan and related compounds.

AFFILIATION: Wuhan Center for Magnetic Resonance, State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan, 430071, People's Republic of China.

Country: England

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MEDLINETA: Magn Reson Chem

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