Structure analysis of monoamine oxidase inhibitors, (R)-5-hydroxymethyl- and (R)-5-methoxymethyl-3-(4-methoxyphenyl)oxazolidin-2-one

Abstract

X-ray single-crystal structures of two recently synthesized inhibitors of monoamine oxidase (MAO) belonging to the aryloxazolidinone family are reported. The first compound is (R)-5-hydroxymethyl-3-(4-methoxyphenyl)oxazolidin-2-one, C 11 H 13 NO 4 (I) and the second is (R)-5-methoxymethyl-3-(4-methoxyphenyl)oxazolidin-2-one, C 12 H 15 NO 4 (II). Both compounds show coplanarity between the phenyl and oxazolidinone rings and electronic delocalization between the heteroatoms of the oxazolidinone moiety as indicated by the bond lengths. The crystal packing is assumed to be by van der Waals interactions. Cohesion is increased in the structure of (I) by the presence of hydrogen bonds