Preparation, crystal structure and antibacterial activity of condensation products of usnic acid and acyl hydrazides
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Sladić, DušanBeljanski, Vladimir
Prelesnik, Bogdan
Bogdanović, Goran
Ivanović, Ivana
Anđelković, Katarina
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Three condensation products of usnic acid with the hydrazides of α-naphthoic, caprylic, and oxamic acids, respectively, have been prepared and characterized by spectrometric methods. A reassignment of the 13C-NMR spectral data of usnic acid has been done. The crystal structure of usnic acid 11-[(1-naphthoyl)hydrazone] ethanol solvate (1:1) has been determined. This substance crystallizes in the monoclinic crystal system, the space group P21, with the unit cell dimensiones a = 7.7365(7) Å, b = 19.632(2) Å, c = 9.4150(15) Å, β = 108.830(11)° V = 1405.0(4) Å3, and Z = 2. At the end of the structure analysis R = 0.055, Rw = 0.052 and S = 0.89. The antibacterial activities of the compounds have been evaluated. The greatest activity against Staphylococcus aureus was found for usnic acid, somewhat lower for the derivatives with hydrazides of α-naphthoic and caprylic acid, and much lower for the derivative with semioxamazide. The activities of these compounds probably depend on their lipophili...city.
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Usnic acid derivatives / NMR spectra / Crystal structure / Biological activity / Acyl hydrazidesSource:
Journal of the Serbian Chemical Society, 1998, 63, 3, 171-182Collections
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VinčaTY - JOUR AU - Sladić, Dušan AU - Beljanski, Vladimir AU - Prelesnik, Bogdan AU - Bogdanović, Goran AU - Ivanović, Ivana AU - Anđelković, Katarina PY - 1998 AB - Three condensation products of usnic acid with the hydrazides of α-naphthoic, caprylic, and oxamic acids, respectively, have been prepared and characterized by spectrometric methods. A reassignment of the 13C-NMR spectral data of usnic acid has been done. The crystal structure of usnic acid 11-[(1-naphthoyl)hydrazone] ethanol solvate (1:1) has been determined. This substance crystallizes in the monoclinic crystal system, the space group P21, with the unit cell dimensiones a = 7.7365(7) Å, b = 19.632(2) Å, c = 9.4150(15) Å, β = 108.830(11)° V = 1405.0(4) Å3, and Z = 2. At the end of the structure analysis R = 0.055, Rw = 0.052 and S = 0.89. The antibacterial activities of the compounds have been evaluated. The greatest activity against Staphylococcus aureus was found for usnic acid, somewhat lower for the derivatives with hydrazides of α-naphthoic and caprylic acid, and much lower for the derivative with semioxamazide. The activities of these compounds probably depend on their lipophilicity. T2 - Journal of the Serbian Chemical Society T1 - Preparation, crystal structure and antibacterial activity of condensation products of usnic acid and acyl hydrazides VL - 63 IS - 3 SP - 171 EP - 182 UR - https://hdl.handle.net/21.15107/rcub_vinar_43 ER -
@article{ author = "Sladić, Dušan and Beljanski, Vladimir and Prelesnik, Bogdan and Bogdanović, Goran and Ivanović, Ivana and Anđelković, Katarina", year = "1998", abstract = "Three condensation products of usnic acid with the hydrazides of α-naphthoic, caprylic, and oxamic acids, respectively, have been prepared and characterized by spectrometric methods. A reassignment of the 13C-NMR spectral data of usnic acid has been done. The crystal structure of usnic acid 11-[(1-naphthoyl)hydrazone] ethanol solvate (1:1) has been determined. This substance crystallizes in the monoclinic crystal system, the space group P21, with the unit cell dimensiones a = 7.7365(7) Å, b = 19.632(2) Å, c = 9.4150(15) Å, β = 108.830(11)° V = 1405.0(4) Å3, and Z = 2. At the end of the structure analysis R = 0.055, Rw = 0.052 and S = 0.89. The antibacterial activities of the compounds have been evaluated. The greatest activity against Staphylococcus aureus was found for usnic acid, somewhat lower for the derivatives with hydrazides of α-naphthoic and caprylic acid, and much lower for the derivative with semioxamazide. The activities of these compounds probably depend on their lipophilicity.", journal = "Journal of the Serbian Chemical Society", title = "Preparation, crystal structure and antibacterial activity of condensation products of usnic acid and acyl hydrazides", volume = "63", number = "3", pages = "171-182", url = "https://hdl.handle.net/21.15107/rcub_vinar_43" }
Sladić, D., Beljanski, V., Prelesnik, B., Bogdanović, G., Ivanović, I.,& Anđelković, K.. (1998). Preparation, crystal structure and antibacterial activity of condensation products of usnic acid and acyl hydrazides. in Journal of the Serbian Chemical Society, 63(3), 171-182. https://hdl.handle.net/21.15107/rcub_vinar_43
Sladić D, Beljanski V, Prelesnik B, Bogdanović G, Ivanović I, Anđelković K. Preparation, crystal structure and antibacterial activity of condensation products of usnic acid and acyl hydrazides. in Journal of the Serbian Chemical Society. 1998;63(3):171-182. https://hdl.handle.net/21.15107/rcub_vinar_43 .
Sladić, Dušan, Beljanski, Vladimir, Prelesnik, Bogdan, Bogdanović, Goran, Ivanović, Ivana, Anđelković, Katarina, "Preparation, crystal structure and antibacterial activity of condensation products of usnic acid and acyl hydrazides" in Journal of the Serbian Chemical Society, 63, no. 3 (1998):171-182, https://hdl.handle.net/21.15107/rcub_vinar_43 .