FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida

Scientific paper - Original scientific paper

• Title (english): FT-IR and NMR spectroscopic studies of salicylic acid derivatives. I. Gentisamide - a metabolite of salicylamide
• Author: Milena Jadrijević-Mladar Takač
• Author: Dražen Vikić Topić
• Author: Tihana Govorčinović
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of medicinal chemistry)
• Scientific / art field, discipline and subdiscipline: BIOMEDICINE AND HEALTHCARE; Pharmacy; Pharmacy

Abstract (croatian)

Gentizinamid (GAM), metabolit prvog prolaska salicilamida (SAM), analiziran je uporabom FT-IR, te jednodimenzijskom i dvodimenzijskom homo- i heteronuklearnom 1H i 13C NMR spektroskopijom.
GAM je izoliran iz ljudskog urina osam sati nakon oralne primjene SAM-a, a strukturna analiza provedena je pomoću FT-IR, 1H i 13C NMR uporabom kemijskih i supstituentnih pomaka, konstanti spin-spin sprege, te povezanosti u COSY, NOESY, HETCOR i HBMC spektrima.
Iz NOESY spektra DMSO-d zaključeno je da su protoni amidne skupine gentizinamida usmjereni prema orto-protonu na C-6 položaju. Rezultati ukazuju na to da prisustvo dodatne fenolne skupine C5-OH u GAM favorizira stvaranje intramolekulske vodikove veze O...HO tipa između C2-OH protona i kisika amidne skupine.

Abstract (english)

Gentisamide (GAM, 2,5-dihydroxybenzamide), a minor first-pass metabolite of salicylamide (SAM, 2-hydroxybenzamide), was studied using FT-IR, 1D and 2D homo- and heteronuclear 1H and 13C NMR spectroscopy.
GAM was isolated from human urine eight hours after oral administration of SAM. FT-IR, 1H and 13C NMR spectra unequivocally confirmed the chemical structure of GAM through chemical and substituent shifts, coupling constants and connectivities in COSY, NOESY, HETCOR and HBMC spectra.
From NOESY spectra of GAM in DMSO-d6, it was concluded that the amide protons are oriented toward the ortho-proton at C-6. Obtained results indicate that the presence of the additional phenol group at C-5 in GAM favours the formation of intramolecular hydrogen bonding of the O…HO type between C2-OH proton and oxygen atom of the amide group.

• Keywords (croatian): gentizinamid; salicilamid; NSAID; biotransformacija, FT-IR; 1D i 2D homo- i heteronuklearna 1H u 13C NMR
• Keywords (english): gentisamide; NSAID; salicylamide; biotransformation; FT-IR; 1D and 2D homo- and heteronuclear 1H and 13C NMR
• Language: croatian
• Language: english
• Publication type: Scientific paper - Original scientific paper
• Publication status: Published
• Peer review: Peer review - international
• Publication version: Published version
• Journal title: Acta Pharmaceutica
• Numbering: vol. 54, no. 3, pp. 163-176
• p-ISSN: 1330-0075
• e-ISSN: 1846-9558
• URN:NBN: urn:nbn:hr:163:224656
• Publication: 2004
• Document URL: https://hrcak.srce.hr/16861
• Type of resource: Text
• Access conditions: Open access
• Created on: 2020-04-09 13:58:39