A DFT investigation of structure, spectroscopic properties and tautomerism of the anticonvulsant drug Lyrica

作者：Sadeghzade Zohre; Beyramabadi S Ali^*; Morsali Ali

来源：Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy , 2015, 138: 637-642.

DOI：10.1016/j.saa.2014.11.069

• Pregabalin
• Lyrica
• DFT
• PCM
• Tautomerism
• Intramolecular proton transfer

The Lyrica (Pregabalin) is a novel anticonvulsant and neuropathic pain drug, which could exist as four possible conformers. Herein, employing density functional theory (DFT), and handling the solvent effects with the PCM model, the structural parameters, energetic behavior, natural bond orbital analysis (NBO), as well as tautomerism mechanization of the Lyrica are investigated. The L1 (-OH form) is the most stable conformer of the Lyrica, which can be tautomerized to the L5 (-NH form) tautomer. The tautomerism reaction includes an intramolecular-proton transfer, which affects considerably the structural parameters and atomic charges of the L1. The OFT-computed NMR chemical shifts and IR vibrational frequencies are good in agreement with the experimental values, confirming suitability of the optimized geometry for the Lyrica.

• 出版日期2015-3-5