15N isotope effects have been used for structural elucidation of the di-substituted thiazole 1-DFL 23805, a novel and potent dual CXCR1/CXCR2 inhibitor, developed by Dompé within the MedChem program. The compound and its 15N isotopologue have been synthesized according to the same proprietary procedure. The 1H and 13C NMR spectra have been measured. The isotope effects on chemical shifts and on coupling constants have been studied in detail. The collected data highlight a new perspective on the elucidation of disubstituted thiazole system, as only very few reference data have been published so far. All the results are consistent with the 2,4 regioisomery assignment.
Guzzo, T., Aramini, A., Lillini, S., Nepravishta, R., Paci, M., Topai, A. (2015). The 15N induced isotope shift as an effective tool for the structure elucidation of 2,4 and 2,5 di-substituted thiazoles. TETRAHEDRON LETTERS, 56(30), 4455-4458 [10.1016/j.tetlet.2015.05.084].
The 15N induced isotope shift as an effective tool for the structure elucidation of 2,4 and 2,5 di-substituted thiazoles
NEPRAVISHTA, RIDVAN;PACI, MAURIZIO;
2015-01-01
Abstract
15N isotope effects have been used for structural elucidation of the di-substituted thiazole 1-DFL 23805, a novel and potent dual CXCR1/CXCR2 inhibitor, developed by Dompé within the MedChem program. The compound and its 15N isotopologue have been synthesized according to the same proprietary procedure. The 1H and 13C NMR spectra have been measured. The isotope effects on chemical shifts and on coupling constants have been studied in detail. The collected data highlight a new perspective on the elucidation of disubstituted thiazole system, as only very few reference data have been published so far. All the results are consistent with the 2,4 regioisomery assignment.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
