Conformational evaluation and detailed 1H and 13C NMR assignments of flavoxate, a urinary tract antispasmodic agent

Nury Pérez-Hernández, Martha S. Morales-Ríos, Carlos M. Cerda-García-Rojas, Pedro Joseph-Nathan

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (Scopus)

Abstract

1H and 13C NMR chemical shift assignments for the urinary tract antispasmodic flavoxate (1) and flavoxate hydrochloride (2) were obtained from one- and two-dimensional measurements. A Monte Carlo random search using molecular mechanics, followed by geometry optimization of each minimum energy structure employing DFT calculations at the B3LYP/6-31G* level, and a Boltzmann analysis of the total energies, provided accurate molecular models which describe the conformational behavior of flavoxate (1). The electron density surfaces for the global minimum and the second minimum conformers 1a and 1b of this L-type Ca2+ channel inhibitor were calculated. The presence of both conformers in solution was demonstrated in full agreement with 2D NOESY data and NOE difference spectroscopy. © 2005 Elsevier B.V. All rights reserved.
Original languageAmerican English
Pages (from-to)603-609
Number of pages542
JournalJournal of Pharmaceutical and Biomedical Analysis
DOIs
StatePublished - 3 May 2006
Externally publishedYes

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Flavoxate
Parasympatholytics
Urinary Tract
Nuclear magnetic resonance
nuclear magnetic resonance
evaluation
dimensional measurement
Molecular mechanics
Molecular Models
hydrochlorides
Chemical shift
Mechanics
Discrete Fourier transforms
inhibitors
Carrier concentration
chemical equilibrium
Spectrum Analysis
Spectroscopy
Electrons
optimization

Cite this

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title = "Conformational evaluation and detailed 1H and 13C NMR assignments of flavoxate, a urinary tract antispasmodic agent",
abstract = "1H and 13C NMR chemical shift assignments for the urinary tract antispasmodic flavoxate (1) and flavoxate hydrochloride (2) were obtained from one- and two-dimensional measurements. A Monte Carlo random search using molecular mechanics, followed by geometry optimization of each minimum energy structure employing DFT calculations at the B3LYP/6-31G* level, and a Boltzmann analysis of the total energies, provided accurate molecular models which describe the conformational behavior of flavoxate (1). The electron density surfaces for the global minimum and the second minimum conformers 1a and 1b of this L-type Ca2+ channel inhibitor were calculated. The presence of both conformers in solution was demonstrated in full agreement with 2D NOESY data and NOE difference spectroscopy. {\circledC} 2005 Elsevier B.V. All rights reserved.",
author = "Nury P{\'e}rez-Hern{\'a}ndez and Morales-R{\'i}os, {Martha S.} and Cerda-Garc{\'i}a-Rojas, {Carlos M.} and Pedro Joseph-Nathan",
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Conformational evaluation and detailed 1H and 13C NMR assignments of flavoxate, a urinary tract antispasmodic agent. / Pérez-Hernández, Nury; Morales-Ríos, Martha S.; Cerda-García-Rojas, Carlos M.; Joseph-Nathan, Pedro.

In: Journal of Pharmaceutical and Biomedical Analysis, 03.05.2006, p. 603-609.

Research output: Contribution to journalArticleResearchpeer-review

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AB - 1H and 13C NMR chemical shift assignments for the urinary tract antispasmodic flavoxate (1) and flavoxate hydrochloride (2) were obtained from one- and two-dimensional measurements. A Monte Carlo random search using molecular mechanics, followed by geometry optimization of each minimum energy structure employing DFT calculations at the B3LYP/6-31G* level, and a Boltzmann analysis of the total energies, provided accurate molecular models which describe the conformational behavior of flavoxate (1). The electron density surfaces for the global minimum and the second minimum conformers 1a and 1b of this L-type Ca2+ channel inhibitor were calculated. The presence of both conformers in solution was demonstrated in full agreement with 2D NOESY data and NOE difference spectroscopy. © 2005 Elsevier B.V. All rights reserved.

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