Logo

Publikacije (29)

Nazad
U. Glamočlija, S. Padhye, S. Špirtović-Halilović, A. Osmanović, E. Veljović, S. Roca, I. Novaković, B. Mandic et al.

Thymoquinone (TQ), a natural compound with antimicrobial and antitumor activity, was used as the starting molecule for the preparation of 3-aminothymoquinone (ATQ) from which ten novel benzoxazole derivatives were prepared and characterized by elemental analysis, IR spectroscopy, mass spectrometry and NMR (1H, 13C) spectroscopy in solution. The crystal structure of 4-methyl-2-phenyl-7-isopropyl-1,3-benzoxazole-5-ol (1a) has been determined by X-ray diffraction. All compounds were tested for their antibacterial, antifungal and antitumor activities. TQ and ATQ showed better antibacterial activity against tested Gram-positive and Gram-negative bacterial strains than benzoxazoles. ATQ had the most potent antifungal effect against Candida albicans, Saccharomyces cerevisiae and Aspergillus brasiliensis. Three benzoxazole derivatives and ATQ showed the highest antitumor activities. The most potent was 2-(4-fluorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1f). Western blot analyses have shown that this compound inhibited phosphorylation of protein kinase B (Akt) and Insulin-like Growth Factor-1 Receptor (IGF1R β) in HeLa and HepG2 cells. The least toxic compound against normal fibroblast cells, which maintains similar antitumor activities as TQ, was 2-(4-chlorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1e). Docking studies indicated that 1e and 1f have significant effects against selected receptors playing important roles in tumour survival.

S. Zukić, E. Veljović, S. Špirtović-Halilović, Samija Muratović, A. Osmanović, S. Trifunović, I. Novaković, D. Završnik

Ten biologically active 2,2,5,5-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives were synthesized and their structures were confirmed by IR, 1H and 13C NMR spectroscopy and mass spectrometry. Synthesized compounds were scanned for their antioxidant, antimicrobial and antiproliferative activity. Antibacterial activity was tested by the diffusion and dilution method against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa, while antifungal activity was tested against Candida albicans and Saccharomyces cerevisiae. Antiproliferative activity was tested against HeLa (cervical carcinoma), SW620 (colorectal adenocarcinoma, metastatic), hepatocellular carcinoma (HEpG2), lung carcinoma cells (A549) and mouse embryo fibroblast cell line (3T3). The best antioxidant activity showed compound 2 with two hydroxy groups substituted on phenyl ring in positions 2' and 3'. The best antimicrobial activity of all synthesized compounds showed compound 8, while the best antiproliferative activity showed compound 6. Results signify the importance of xanthene-1,8-dione derivatives as potential antioxidant and antiproliferative agents.

E. Veljović, S. Špirtović-Halilović, Samija Muratović, L. V. Žulj, S. Roca, S. Trifunović, A. Osmanović, D. Završnik

Ten 9-aryl substituted hydroxylated xanthen-3-ones, including three new compounds (III) are synthesized using a reliable one-pot synthesis.

E. Veljović, S. Špirtović-Halilović, Samija Muratović, L. V. Žulj, S. Roca, S. Trifunović, A. Osmanović, D. Završnik

Oxidative stress is directly related to several diseases and symptoms, where antioxidant compounds, such as xanthenes, may become important in prevention and/or treatmant. Ten biologically active 9-aryl substituted 2, 6, 7-trihydroxyxanthen-3-one derivatives were synthesized using reliable one-pot synthesis and their structures were confirmed by IR, 1H and 13C NMR spectroscopy and mass spectrometry. Some of the synthesized compounds were scanned for their antioxidant potency using electrochemical method cyclic voltammetry of immobilized microparticles. Substitution of hydrogen at the phenyl ring of 2, 6, 7-trihydroxy-9-phenylxanthen-3-one with an electron-donating group affected the reducing power of the compounds by lowering the biological oxidation potential. These results signify the importance of xanthen-3-one derivatives as antioxidant agents and their further biological evaluation.

S. Špirtović-Halilović, M. Salihović, S. Trifunović, S. Roca, E. Veljović, A. Osmanović, M. Vinkoviċ, D. Završnik

For some synthesized coumarin derivatives, 1H and 13C NMR isotropic chemical shifts and some other molecular properties were calculated using density functional theory. The calculations yield reliable results, that are in good correlation with experimental data. This is a good basis for the collaboration between experimentalists and quantum chemists.

Objective: As a further part of our chemical and biological studies in this field, we describe the preparations of the properly substituted benzylidene-bis-(4-hydroxycoumarin) derivatives 5a-h and 3-(6-oxo-(1H)-benzopyrano[4,3-b]benzopyran-7-yl)-4-hydroxycoumarin derivatives 6a-e . Methods: The synthesized compounds were screened for their in vitro antimicrobial activity against five strains of bacteria and two fungal strains using disk diffusion assay and dilution method. The way in which the substituent group’s physicochemical properties influence the antimicrobial activity is discussed in the paper. Results: The in vitro evaluation of their inhibitory properties towards five strains of Gram-positive and Gram-negative bacteria and two fungal strains indicated that the                                       4-trifluoromethylbenzylidene derivative of bis-(4-hydroxycoumarin) (compound 5c ) and                    3-(6-oxo-(1 H )-18-bromobenzopyrano[4,3-b]benzopyran-7-yl)-4-hydroxycoumarin derivative (compound 6b ) possess the most potent antibacterial activities, with MIC of 3.9 μg/mL - 7.8 μg/mL against Gram-positive bacteria. Conclusion: The compound 6b has greater antibacterial activity than the standard chloramfenicol (inhibition zone 26 mm and MIC 1.9 μg/mL) against Staphyloccocus aureus and could be considered as leading compound in the future antimicrobial drug development. Key words: Benzylidene-bis-(4-hydroxycoumarin), benzopyranocoumarin derivatives, antibacterial assays , antifungal activity.

Andrijana Meščić, D. Glavač, A. Osmanović, D. Završnik, M. Cetina, D. Makuc, J. Plavec, S. Ametamey et al.

Andrijana Meščić, Svjetlana Krištafor, I. Novaković, A. Osmanović, U. Müller, D. Završnik, S. Ametamey, L. Scapozza et al.

The efficient syntheses of 5-(2-hydroxyethyl)- and 5-(3-hydroxypropyl)-substituted pyrimidine derivatives bearing 2,3-dihydroxypropyl, acyclovir-, ganciclovir- and penciclovir-like side chains are reported. A synthetic approach that included the alkylation of an N-anionic-5-substituted pyrimidine intermediate (method A) provided the target acyclonucleosides in significantly higher overall yields in comparison to those obtained by method B using sylilation reaction. The phosphorylation assays of novel compounds as potential substrates for thymidine kinase of herpes simplex virus type 1 (HSV-1 TK) showed that solely pyrimidine 5-substituted acyclonucleosides with a penciclovir-like side chain acted as a fraudulent substrates of HSV-1 TK. Moreover, the uracil derivative with penciclovir-like side chain with less bulky 2-hydroxyethyl substituent at C-5 proved to be a better substrate than the corresponding one with a 3-hydroxypropyl substituent. Therefore, this acyclonucleoside was selected as a lead compound for the development of a positron emission tomography HSV-1 TK activity imaging agent.

D. Završnik, E. Veljović, Adnan Bajrović, Martina Vrankić, B. Gržeta, A. Osmanović, S. Špirtović-Halilović, Samija Muratović

Series of synthesized xanthen-3-one derivatives were analyzed for thermal characteristics by differential scanning calorimetry (DSC), as well as for crystallinity using X-ray powder diffraction. Xanthen-3-one derivatives are prepared according to the well known procedure which includes two-fold Friedel-Crafts alkylation. The aim of this research was to determine purity and crystallinity of synthesized xanthen-3-one derivatives. Thermograms of synthesized compounds showed that compounds have purity above 98%, while crystallographic analysis of powder showed that the compounds have a 10-30% crystalline form.

Nema pronađenih rezultata, molimo da izmjenite uslove pretrage i pokušate ponovo!

Pretplatite se na novosti o BH Akademskom Imeniku

Ova stranica koristi kolačiće da bi vam pružila najbolje iskustvo

Saznaj više