TY  - JOUR
AU  - Glamoclija, Una
AU  - Padhye, Subhash
AU  - Spirtovic-Halilovic, Selma
AU  - Osmanovic, Amar
AU  - Veljović, Elma
AU  - Roca, Suncica
AU  - Novaković, Irena
AU  - Mandić, Boris
AU  - Turel, Iztok
AU  - Kljun, Jakob
AU  - Trifunović, Snežana
AU  - Kahrovic, Emira
AU  - Kraljević Pavelić, Sandra
AU  - Harej, Anja
AU  - Klobucar, Marko
AU  - Zavrsnik, Davorka
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2403
AB  - 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 (H-1, C-13) 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 ) 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.
PB  - MDPI
T2  - Molecules
T1  - Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone
VL  - 23
IS  - 12
DO  - 10.3390/molecules23123297
ER  - 

@article{
author = "Glamoclija, Una and Padhye, Subhash and Spirtovic-Halilovic, Selma and Osmanovic, Amar and Veljović, Elma and Roca, Suncica and Novaković, Irena and Mandić, Boris and Turel, Iztok and Kljun, Jakob and Trifunović, Snežana and Kahrovic, Emira and Kraljević Pavelić, Sandra and Harej, Anja and Klobucar, Marko and Zavrsnik, Davorka",
year = "2018",
abstract = "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 (H-1, C-13) 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 ) 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.",
publisher = "MDPI",
journal = "Molecules",
title = "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone",
volume = "23",
number = "12",
doi = "10.3390/molecules23123297"
}

Glamoclija, U., Padhye, S., Spirtovic-Halilovic, S., Osmanovic, A., Veljović, E., Roca, S., Novaković, I., Mandić, B., Turel, I., Kljun, J., Trifunović, S., Kahrovic, E., Kraljević Pavelić, S., Harej, A., Klobucar, M.,& Zavrsnik, D.. (2018). Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. in Molecules
MDPI., 23(12).
https://doi.org/10.3390/molecules23123297

Glamoclija U, Padhye S, Spirtovic-Halilovic S, Osmanovic A, Veljović E, Roca S, Novaković I, Mandić B, Turel I, Kljun J, Trifunović S, Kahrovic E, Kraljević Pavelić S, Harej A, Klobucar M, Zavrsnik D. Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone. in Molecules. 2018;23(12).
doi:10.3390/molecules23123297 .

Glamoclija, Una, Padhye, Subhash, Spirtovic-Halilovic, Selma, Osmanovic, Amar, Veljović, Elma, Roca, Suncica, Novaković, Irena, Mandić, Boris, Turel, Iztok, Kljun, Jakob, Trifunović, Snežana, Kahrovic, Emira, Kraljević Pavelić, Sandra, Harej, Anja, Klobucar, Marko, Zavrsnik, Davorka, "Synthesis, Biological Evaluation and Docking Studies of Benzoxazoles Derived from Thymoquinone" in Molecules, 23, no. 12 (2018),
https://doi.org/10.3390/molecules23123297 . .

TY  - JOUR
AU  - Zukic, Selma
AU  - Veljović, Elma
AU  - Spirtovic-Halilovic, Selma
AU  - Muratovic, Samija
AU  - Osmanovic, Amar
AU  - Trifunović, Snežana
AU  - Novaković, Irena
AU  - Zavrsnik, Davorka
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2430
AB  - Ten biologically active 2,2,5,5-tetramethy1-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives were synthesized and their structures were confirmed by IR, H-1 and C-13 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 a ntifunga I 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.
PB  - Croatian Chemical Soc, Zagreb
T2  - Croatica Chemica Acta
T1  - Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives
VL  - 91
IS  - 1
SP  - 1
EP  - 9
DO  - 10.5562/cca3225
ER  - 

@article{
author = "Zukic, Selma and Veljović, Elma and Spirtovic-Halilovic, Selma and Muratovic, Samija and Osmanovic, Amar and Trifunović, Snežana and Novaković, Irena and Zavrsnik, Davorka",
year = "2018",
abstract = "Ten biologically active 2,2,5,5-tetramethy1-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives were synthesized and their structures were confirmed by IR, H-1 and C-13 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 a ntifunga I 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.",
publisher = "Croatian Chemical Soc, Zagreb",
journal = "Croatica Chemica Acta",
title = "Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives",
volume = "91",
number = "1",
pages = "1-9",
doi = "10.5562/cca3225"
}

Zukic, S., Veljović, E., Spirtovic-Halilovic, S., Muratovic, S., Osmanovic, A., Trifunović, S., Novaković, I.,& Zavrsnik, D.. (2018). Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives. in Croatica Chemica Acta
Croatian Chemical Soc, Zagreb., 91(1), 1-9.
https://doi.org/10.5562/cca3225

Zukic S, Veljović E, Spirtovic-Halilovic S, Muratovic S, Osmanovic A, Trifunović S, Novaković I, Zavrsnik D. Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives. in Croatica Chemica Acta. 2018;91(1):1-9.
doi:10.5562/cca3225 .

Zukic, Selma, Veljović, Elma, Spirtovic-Halilovic, Selma, Muratovic, Samija, Osmanovic, Amar, Trifunović, Snežana, Novaković, Irena, Zavrsnik, Davorka, "Antioxidant, Antimicrobial and Antiproliferative Activities of Synthesized 2,2,5,5-Tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione Derivatives" in Croatica Chemica Acta, 91, no. 1 (2018):1-9,
https://doi.org/10.5562/cca3225 . .