6533b859fe1ef96bd12b80b8

RESEARCH PRODUCT

Structural studies of acyl esters of entacapone

Elina WegeliusJukka GyntherJuhani HuuskonenTapio NevalainenJukka LeppänenTomi Järvinen

subject

StereochemistryOrganic ChemistryCrystal structureProdrugCarbon-13 NMRCOMT inhibitorAnalytical ChemistryInorganic Chemistrychemistry.chemical_compoundchemistrymedicineEntacaponeFree rotationSpectroscopymedicine.drug

description

Abstract The crystal structures of entacapone [(E)-2-cyano-N,N-diethyl-3-(3,4-dihydroxy-5-nitrophenyl)propenamide] and three of its acyl esters were solved. Entacapone, and its monopivaloate and diacetate derivatives, exist in the E-form while its dibenzoate derivative adopts the Z-form in the crystalline state. The ethyl substituents of the E-form are not freely rotating, as demonstrated by the broad signals in the 1H and 13C NMR spectra. The rotation barrier for the E-form was defined by the crystal structures, which show that free rotation of the ethyl substituents is blocked by the cyano-group.

yearjournalcountryeditionlanguage
2001-05-01Journal of Molecular Structure
https://doi.org/10.1016/s0022-2860(00)00859-0