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Pregled bibliografske jedinice broj: 296697

A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy


Rajić, Zrinka; Jadrijević-Mladar Takač, Milena; Vinković, Marijana; Zorc, Branka; Takač, Vedran
A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy // 3rd Pharmaceutical Sciences World Congress (PSWC) - Optimising Drug Therapy: An Imperative for World Health, Abstracts on CD-ROM / Boquist, Camilia ; Linden, H. Hans (ur.).
The Hague: International Pharmaceutical Federation, Board of Pharmaceutical Sciences, 2007. (poster, međunarodna recenzija, sažetak, znanstveni)


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Naslov
A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy

Autori
Rajić, Zrinka ; Jadrijević-Mladar Takač, Milena ; Vinković, Marijana ; Zorc, Branka ; Takač, Vedran

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
3rd Pharmaceutical Sciences World Congress (PSWC) - Optimising Drug Therapy: An Imperative for World Health, Abstracts on CD-ROM / Boquist, Camilia ; Linden, H. Hans - The Hague : International Pharmaceutical Federation, Board of Pharmaceutical Sciences, 2007

Skup
3rd Pharmaceutical Sciences World Congress (PSWC) - Optimising Drug Therapy: An Imperative for World Health

Mjesto i datum
Amsterdam, The Netherlands, 22-25.04.2007

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
NSAID; hydroxamic acids; H-bond; FTIR; 1H and 13C one- and twodimensional NMR spectroscopy

Sažetak
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).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija



POVEZANOST RADA


Projekt / tema
4858 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, MZOS)
3917 - Sinteza, karakterizacija i djelovanje potencijalnih i poznatih ljekovitih tvari (Branka Zorc, MZOS)
929 - Modeliranje molekula i materijala metodama matematičke i računarske kemije (Ante Graovac, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Citiraj ovu publikaciju

Rajić, Zrinka; Jadrijević-Mladar Takač, Milena; Vinković, Marijana; Zorc, Branka; Takač, Vedran
A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy // 3rd Pharmaceutical Sciences World Congress (PSWC) - Optimising Drug Therapy: An Imperative for World Health, Abstracts on CD-ROM / Boquist, Camilia ; Linden, H. Hans (ur.).
The Hague: International Pharmaceutical Federation, Board of Pharmaceutical Sciences, 2007. (poster, međunarodna recenzija, sažetak, znanstveni)
Rajić, Z., Jadrijević-Mladar Takač, M., Vinković, M., Zorc, B. & Takač, V. (2007) A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy. U: Boquist, C. & Linden, H. (ur.)3rd Pharmaceutical Sciences World Congress (PSWC) - Optimising Drug Therapy: An Imperative for World Health, Abstracts on CD-ROM.
@article{article, year = {2007}, keywords = {NSAID, hydroxamic acids, H-bond, FTIR, 1H and 13C one- and twodimensional NMR spectroscopy}, title = {A Study of H-bond in a Group of NSAID Hydroxamic Acid Derivatives by FTIR and NMR Spectroscopy}, keyword = {NSAID, hydroxamic acids, H-bond, FTIR, 1H and 13C one- and twodimensional NMR spectroscopy}, publisher = {International Pharmaceutical Federation, Board of Pharmaceutical Sciences}, publisherplace = {Amsterdam, The Netherlands} }




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