An ab initio structural study of some derivatives of ibuprofen as possible anti-inflammatory agents

Villa, M.; Smeyers, Nadine J.; Senent, María Luisa; Smeyers, Yves G.

doi:10.1016/s0166-1280(00)00683-7

Cited by 10 publications

(8 citation statements)

References 8 publications

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“…To verify the quality of the theoretical calculations, the electronic densities, calculated by the Gaussian 98 package in the gas phase and in solution, on the α‐carbon atom of the carboxylic moiety, the α‐carbon atoms of the benzene ring, as well as the hydrogen atom bearing by these atoms were compared with the 13 C and 1 H chemical shifts in Table III, as in Refs. 9 and 13, in ibufenac, ibuprofen, and α‐methyl‐ibuprofen. Note that the RMN measurements of the chemical shifts were performed in CDCl 3 solution, which possesses a dielectric constant between those of water and vacuum.…”

Section: Calculations and Resultsmentioning

confidence: 99%

“…Finally, in Ref. 13 the conformations of the acid moiety, the rotational barriers, as well as the protonation energies were again calculated in ibufenac, ibuprofen, and α‐methyl‐, α‐fluor‐, and α‐chloro‐ibuprofen, using an ab initio approach at the restricted Hartree–Fock (RHF) level with the polarized 6‐311G** basis set. It was found that although the protonation energy keeps being an activity factor the conformation factor should be replaced by the rotational barrier of the acidic moiety.…”

Section: Introductionmentioning

confidence: 99%

“…In the present work, a series of α‐substituted 2‐ p ‐isobutyl‐phenylpropionic acids will be considered, as well as the 5‐isopropyl‐1 H ‐indene‐2,3‐dihydro‐1‐carboxylic acid, with the same accuracy level of approximation as in Ref. 13, but in water solution, and the results will be compared with those obtained in the gas phase and the available experimental data for the biologic activity.…”

Section: Introductionmentioning

confidence: 99%

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Percutaneous closure of perimembranous ventricular septal defects with the Amplatzer device: Technical and morphological considerations

Pedra

Esteves

et al. 2004

Cathet Cardio Intervent

135

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Percutaneous closure of perimembranous ventricular septal defects (VSDs) has been feasible, safe, and effective with the new Amplatzer membranous septal occluder. We report further experience with this device with emphasis on morphological aspects of the VSDs and technical issues. Ten patients (median age and weight, 14 years and 34.5 kg, respectively) with volume-overloaded left ventricles underwent closure under general anesthesia and transesophageal guidance (TEE). The VSD diameter was 7.1 +/- 4.0 mm by angiography and 7.8 +/- 3.7 mm by TEE. Three patients had defects associated with aneurysm-like formations (two with multiple exit holes), four had defects shrouded by extensive tricuspid valve tissue, two had defects with little or no tricuspid valve involvement, and one had a right aortic cusp prolapse with trivial aortic regurgitation. Implantation was successful in all patients, although in two the initial device had to be changed for a larger one. Kinkings in the delivery sheath, inability to position the sheath near the left ventricular apex, and device prolapse through the VSD prompted modifications in the standard technique of implantation. Device orientation was excellent except in one case. Nine patients had complete occlusion within 1-3 months. Device-related aortic or tricuspid insufficiency, arrhythmias, and embolization were not observed. Two patients had slight gradients across the left ventricular outflow tract, normalizing after 3 months. The Amplatzer membranous septal occluder was suitable to close a wide range of perimembranous VSD sizes and morphologies with good short-term outcomes. Longer follow-up is required.

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Section: Calculations and Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Percutaneous closure of perimembranous ventricular septal defects with the Amplatzer device: Technical and morphological considerations

Pedra

Esteves

et al. 2004

Cathet Cardio Intervent

135

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“…The knowledge of the conformational preferences of some nonsteroidal anti‐inflammatory drugs (NSAID's), particularly the substituted α‐arylpropionic acids, is of the utmost importance for a better understanding of the structure–activity relationships (SAR's) underlying their biological activity, as well as of their mechanism of action, which can be related to the ability to inhibit prostaglandin synthesis 1–3. In fact, several studies are reported which establish the monocarboxylic acid group responsible for the anti‐inflammatory, analgesic, and antipyretic properties of these compounds 4–6. However, different ring substitution is known to give rise to distinct pharmacological properties, probably due to pharmacokinetic and pharmacodynamic variations.…”

Section: Introductionmentioning

confidence: 99%

Conformational Stability of Ibuprofen: Assessed by DFT Calculations and Optical Vibrational Spectroscopy

Vueba

Pina

Carvalho

2008

Journal of Pharmaceutical Sciences

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A thorough conformational analysis of ibuprofen [2-(4-isobutylphenyl) propionic acid] was carried by out, using density functional theory (DFT) calculations coupled to optical vibrational spectroscopy (both Raman and FTIR). Eight different geometries were found to be energy minima. The relative orientations of the substituent groups in the ibuprofen molecule, which can be considered as a para-substituted phenyl ring, were verified to hardly affect its conformational stability. The internal rotations converting the calculated conformers of ibuprofen were studied and the intramolecular interactions governing the conformational preferences of the molecule were analyzed by quantitative potential energy deconvolution using Fourier type profiles. The harmonic vibrational frequencies and corresponding intensities were calculated for all the conformers obtained, leading to the assignment of the spectra, and evidencing the sole presence of one of the lowest energy conformers in the solid state. Vibrational spectroscopic proof of intermolecular hydrogen bonds between the carboxylic groups of adjacent ibuprofen molecules, leading to the formation of dimers, was also obtained. ß

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“…data and anti-inflamatory activities [15]. The barrier height associated with rotation of the propionic acid moiety and deprotonation energy were considered to be descriptors for anti-inflamatory activity.…”

Section: Ibuprofenmentioning

confidence: 99%

Gas phase conformation in the ibuprofen analogues isobutylbenzene and 2-phenylpropionic acid

Robertson¹,

Morrison²

2005

Molecular Physics

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The S 1 S 0 transitions of isobutylbenzene (IBB) and 2-phenylpropionic acid (2PPA) have been studied in a supersonic jet expansion by resonant 2-photon ionization (R2PI). Conformational assignments have been made with the aid of ab initio molecular orbital calculations on the ground and excited electronic states. Dominant features in the IBB spectrum are assigned to conformer AG, where A and G refer to anti and gauche arrangements of the two methyl groups with respect to the C -C bond. Additional weak features are assigned to a higher energy GG conformer, present in low concentration in the jet. Four possible conformers of 2PPA are predicted, but the R2PI spectrum provides evidence of only one. A low barrier to interconversion between the two most stable conformers suggests that the higher energy form is depopulated by relaxation occurring in the jet expansion.

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An ab initio structural study of some derivatives of ibuprofen as possible anti-inflammatory agents

Cited by 10 publications

References 8 publications

Percutaneous closure of perimembranous ventricular septal defects with the Amplatzer device: Technical and morphological considerations

Percutaneous closure of perimembranous ventricular septal defects with the Amplatzer device: Technical and morphological considerations

Conformational Stability of Ibuprofen: Assessed by DFT Calculations and Optical Vibrational Spectroscopy

Gas phase conformation in the ibuprofen analogues isobutylbenzene and 2-phenylpropionic acid

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