A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy (CROSBI ID 527665)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija
Podaci o odgovornosti
Rajić, Zrinka ; Jadrijević-Mladar Takač, Milena ; Vinković, Marijana ; Zorc, Branka ; Takač, Vedran
engleski
A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy
The growing interest in the synthesis of therapeutics based on the hydroxamic functional group(s) is observed, although the structures of hydroxamic acids are still the subject of many controversies, among others due to the possibility of keto-iminol tautomerism. On the other hand, hydroxamic acids can exist in the form of cis (Z) - and/or trans (E)-conformers (relative to C-N bond) which are stabilized by intra- or intermolecular hydrogen bonds. The conformational behaviour of a series of monohydroxamic acids, derivatives of NSAIDs (ibuprofen, fenprofen, ketoprofen, diclophenac and indomethacin) in DMSO solution and in the solid state has been investigated using FTIR and one- and two-dimesional homo and heteronuclear 1H and 13C NMR spectrosopy. Hydroxamic acids were synthesized in the reaction of appropriate reactive NSAID benzotriazolide with hydroxylamine hidrochloride or with benzyloxyamine hidrochloride following the reduction. The results of IR and NMR investigations showed significant hydrogen bonding effects in both, the solid state and solution. NMR spectra (1H and 13C, COSY, NOESY, HMBC, HETCOR) of NSAID hydroxamic acids measured in DMSO-d6 solution have showed that investigated NSAID hydroxamic acids in DMSO solution are in the keto form of cis-(Z) conformer with intramolecular hydrogen bond O-H...O= type. 1H NMR chemical shifts of hydroxamic OH are in the range from 10.12 to 11.47 ppm, and hydroxamic NH from 8.61 to 8.97 , while 13C NMR shifts for hydroxamic C=O are in the range from 167.81 to 170.52 ppm. Findings from NMR analysis are in good agreement with FTIR spectral data of solids (KBr).
NSAID; hydroxamic acids; H-bond; FTIR; 1H and 13C one- and twodimensional NMR spectroscopy
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Podaci o prilogu
2007.
objavljeno
Podaci o matičnoj publikaciji
Boquist, Camilia ; Linden, H. Hans
Hag: International Pharmaceutical Federation, Board of Pharmaceutical Sciences
Podaci o skupu
3rd Pharmaceutical Sciences World Congress (PSWC) - Optimising Drug Therapy: An Imperative for World Health
poster
22.04.2007-25.04.2007
Amsterdam, Nizozemska