prikaz prve stranice dokumenta 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
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Scientific paper - Original scientific paper
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

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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, no. 7, 2011, pp. 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 and 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, no. 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), pp. 6023-6040. doi: 10.3390/molecules16076023

Završnik D, Muratović S, Makuc D, Plavec J, Cetina M, Nagl A, and 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 [cited 2024 October 22];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, no. 7, pp. 6023-6040, 2011. [Online]. Available at: https://urn.nsk.hr/urn:nbn:hr:201:175906. [Accessed: 22 October 2024]

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Title (english)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
AuthorDavorka Završnik
AuthorSamija Muratović
AuthorDamjan Makuc
AuthorJanez Plavec
AuthorMario Cetina
AuthorAnte Nagl
AuthorErik De Clercq
AuthorJan Balzarini
AuthorMladen Mintas
Author's institutionUniversity of Zagreb
Faculty of Textile Technology
(Department of Applied Chemistry)
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract (english)
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.
Keywords (english)
Languageenglish
Publication typeScientific paper - Original scientific paper
Publication statusPublished
Peer reviewPeer review - international
Publication versionPublished version
Journal titleMolecules
Numberingvol. 16, no. 7, pp. 6023-6040
e-ISSN1420-3049
DOIhttps://doi.org/10.3390/molecules16076023
URN:NBNurn:nbn:hr:201:175906
Publication2011
Document URLhttp://www.mdpi.com/1420-3049/16/7/6023
Type of resourceText
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2017-02-10 13:06:48