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Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations
Molecules, 16 (2011), 7; 6023-6040. https://doi.org/10.3390/molecules16076023
Završnik, Davorka; Muratović, Samija; Makuc, Damjan; Plavec, Janez; Cetina, Mario; Nagl, Ante; De Clercq, Erik; Balzarini, Jan; Mintas, Mladen

Institucijski repozitorij: Repozitorij Tekstilno-tehnološkog fakulteta Sveučilišta u Zagrebu

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Završnik, D., Muratović, S., Makuc, D., Plavec, J., Cetina, M., Nagl, A. ... Mintas, M. (2011). Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations. Molecules, 16. (7), 6023-6040. doi: 10.3390/molecules16076023

Završnik, Davorka, et al. "Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations." Molecules, vol. 16, br. 7, 2011, str. 6023-6040. https://doi.org/10.3390/molecules16076023

Završnik, Davorka, Samija Muratović, Damjan Makuc, Janez Plavec, Mario Cetina, Ante Nagl, Erik De Clercq, Jan Balzarini i Mladen Mintas. "Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations." Molecules 16, br. 7 (2011): 6023-6040. https://doi.org/10.3390/molecules16076023

Završnik, D., et al. (2011) 'Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations', Molecules, 16(7), str. 6023-6040. doi: 10.3390/molecules16076023

Završnik D, Muratović S, Makuc D, Plavec J, Cetina M, Nagl A, i sur.. Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations. Molecules [Internet]. 2011. [pristupljeno 01.12.2024.];16(7):6023-6040. doi: 10.3390/molecules16076023

D. Završnik, et al., "Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations", Molecules, vol. 16, br. 7, str. 6023-6040, 2011. [Online]. Dostupno na: https://urn.nsk.hr/urn:nbn:hr:201:175906. [Citirano: 01.12.2024.]

Za citiranje koristite ovu mrežnu adresu: https://urn.nsk.hr/urn:nbn:hr:201:175906
Podaci o radu
Naslov (engleski)Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano- Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations
AutorDavorka Završnik
AutorSamija Muratović
AutorDamjan Makuc
AutorJanez Plavec
AutorMario Cetina
AutorAnte Nagl
AutorErik De Clercq
AutorJan Balzarini
AutorMladen Mintas
Autorova ustanovaSveučilište u Zagrebu
Tekstilno-tehnološki fakultet
(Zavod za primijenjenu kemiju)
Znanstveno / umjetničko
područje, polje i grana		PRIRODNE ZNANOSTI
Kemija
Sažetak (engleski)
We report on the synthesis of 4-hydroxycoumarin dimers 1-15 bearing an aryl substituent on the central linker and fused benzopyranocoumarin derivatives 16-20 and on their in vitro broad anti-DNA and RNA virus activity evaluations. The chemical identities and structure of compounds 1-20 were deduced from their homo- and heteronuclear NMR measurements whereas the conformational properties of 5, 14 and 20 were assessed by the use of 1D difference NOE enhancements. Unequivocal proof of the stereostructure of compounds 7, 9, 16 and 18 was obtained by single crystal X-ray diffraction method. The X-ray crystal structure analysis revealed that two 4-hydroxycoumarin moieties in the 4-trifluoromethylphenyl- and 2-nitrophenyl derivatives (compounds 7 and 9, respectively) are intramolecularly hydrogen-bonded between hydroxyl and carbonyl oxygen atoms. Consequently, the compounds 7 and 9 adopt conformations in which two 4-hydroxycoumarin moieties are anti-disposed. Antiviral activity evaluation results indicated that the 4-bromobenzylidene derivative of bis-(4-hydroxycoumarin) (compound 3) possesses inhibitory activity against HSV-1 (KOS), HSV-2 (G), vaccinia virus and HSV-1 TK- KOS (ACVr) at a concentration of 9-12 mM and at a minimum cytotoxic concentration (MCC) greater than 20 M. Compounds 4-6, 8, and 20 were active against feline herpes virus (50% effective concentration, EC50 = 5-8.1 M), that is at a 4-7-fold lower concentration than the MCC.
Ključne riječi (engleski)
Jezikengleski
Vrsta publikacijeZnanstveni rad - Izvorni znanstveni rad
Status objaveObjavljen
Vrsta recenzijeRecenziran - međunarodna recenzija
Verzija publikacijeObjavljena verzija rada (izdavačev PDF)
Naslov časopisaMolecules
Brojčani podacivol. 16, br. 7, str. 6023-6040
e-ISSN1420-3049
DOIhttps://doi.org/10.3390/molecules16076023
URN:NBNurn:nbn:hr:201:175906
Datum objave publikacije2011
URL dokumentahttp://www.mdpi.com/1420-3049/16/7/6023
Vrsta resursaTekst
Prava pristupaOtvoreni pristup
Uvjeti korištenjaIkona licence Zaštićeno autorskim pravom.
Datum i vrijeme pohrane2017-02-10 13:06:48