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Scientific paper - Original scientific paper
FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida
Acta Pharmaceutica, 54 (2004), 3; 163-176. urn:nbn:hr:163:224656
Jadrijević-Mladar Takač, Milena; Vikić Topić, Dražen; Govorčinović, Tihana

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Jadrijević Mladar Takač, M., Vikić Topić, D. & Govorčinović, T. (2004). FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida. Acta Pharmaceutica, 54. (3), 163-176. Retrieved from https://urn.nsk.hr/urn:nbn:hr:163:224656

Jadrijević Mladar Takač, Milena, et al. "FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida." Acta Pharmaceutica, vol. 54, no. 3, 2004, pp. 163-176. https://urn.nsk.hr/urn:nbn:hr:163:224656

Jadrijević Mladar Takač, Milena, Dražen Vikić Topić and Tihana Govorčinović. "FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida." Acta Pharmaceutica 54, no. 3 (2004): 163-176. https://urn.nsk.hr/urn:nbn:hr:163:224656

Jadrijević Mladar Takač, M., Vikić Topić, D. and Govorčinović, T. (2004) 'FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida', Acta Pharmaceutica, 54(3), pp. 163-176. Available at: https://urn.nsk.hr/urn:nbn:hr:163:224656 (Accessed 26 December 2024)

Jadrijević Mladar Takač M, Vikić Topić D, Govorčinović T. FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida. Acta Pharmaceutica [Internet]. 2004 [cited 2024 December 26];54(3):163-176. Available at: https://urn.nsk.hr/urn:nbn:hr:163:224656

M. Jadrijević Mladar Takač, D. Vikić Topić and T. Govorčinović, "FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida", Acta Pharmaceutica, vol. 54, no. 3, pp. 163-176, 2004. [Online]. Available at: https://urn.nsk.hr/urn:nbn:hr:163:224656. [Accessed: 26 December 2024]

Metadata
Title (croatian)FT-IR i NMR spektroskopska istraživanja derivata salicilne kiselina. I. Gentizinamid- metabolit salicilamida
Title (english)FT-IR and NMR spectroscopic studies of salicylic acid derivatives. I. Gentisamide - a metabolite of salicylamide
AuthorMilena Jadrijević-Mladar Takač
AuthorDražen Vikić Topić
AuthorTihana Govorčinović
Author's institutionUniversity 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)
Keywords (english)
Languagecroatian
Languageenglish
Publication typeScientific paper - Original scientific paper
Publication statusPublished
Peer reviewPeer review - international
Publication versionPublished version
Journal titleActa Pharmaceutica
Numberingvol. 54, no. 3, pp. 163-176
p-ISSN1330-0075
e-ISSN1846-9558
URN:NBNurn:nbn:hr:163:224656
Publication2004
Document URLhttps://hrcak.srce.hr/16861
Type of resourceText
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2020-04-09 13:58:39