Theoretical study on the structure and reactive sites of non-steroidal anti-inflammatory drugs

Producción CyT

Artículo

Autoría

OKULIK, NORA BEATRIZ

Fecha

2004

Editorial y Lugar de Edición

Elsevier

Revista

JOURNAL OF MOLECULAR STRUCTURE THEOCHEM, vol. 6682 (pp. 55-62) Elsevier

Resumen Información suministrada por el agente en SIGEVA

The mode of action of the non-steroid anti-inflammatory drugs (NSAIDs) is attributed primarily to the inhibition of PG synthesis, and more specifically, to the inhibition of the COX enzyme system. In an effort to gain a deeper insight on the properties of NSAIDs as Indometacine, {l-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid}; Diclofenac, {[2-(2,6-dichlorophenyl) amino]-benzeneacetic acid}; and Niflumic acid, {2-3((3-trifluoromethyl)phenylamino)-3-pyridinecarboxylic acid}, that... The mode of action of the non-steroid anti-inflammatory drugs (NSAIDs) is attributed primarily to the inhibition of PG synthesis, and more specifically, to the inhibition of the COX enzyme system. In an effort to gain a deeper insight on the properties of NSAIDs as Indometacine, {l-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid}; Diclofenac, {[2-(2,6-dichlorophenyl) amino]-benzeneacetic acid}; and Niflumic acid, {2-3((3-trifluoromethyl)phenylamino)-3-pyridinecarboxylic acid}, that will provide knowledge of their action, we have performed theoretical studies in the frame of the AIM Bader’s theory (atoms in molecules). The topological properties of the NSAIDs studied show that the C–C, C–N and C–H ring bonds are typical of covalent interactions. The CyO and O–H bonds in the carboxylate groups are strong shared interactions. Hydrogen bonds are only localized in the Niflumic acid. The oxygen atoms of the carboxylic groups are sites of the highest concentration of charge and it is assumed that these atoms shall be the preferred sites for an electrophilic attack.yO and O–H bonds in the carboxylate groups are strong shared interactions. Hydrogen bonds are only localized in the Niflumic acid. The oxygen atoms of the carboxylic groups are sites of the highest concentration of charge and it is assumed that these atoms shall be the preferred sites for an electrophilic attack.

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