Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone

The regioselectivity of the reaction of conjugate addition of thiols, amines, methanol and hydrogen chloride with the monoalkyl-1,4-benzoquinones avarone and 2-tert-butyl-1,4-benzoquinone was investigated. It was shown that the regioselectivity of the reaction is influenced by the electrophilicity of position 5 in unprotonated 2-alkylquinones, the increased electrophilicity of position 6 in acidic medium, and by the acidity of the intermediate hydroquinones.Proučavana je regioselektivnost konjugovane adicije tiola, amina, metanola i hlorovodonika na monoalkil-1,4-benzohinone avaron i 2-tert-butil-1,4-benzohinon. Pokazano je da na regioselektivnost reakcije utiču elektrofilnost položaja 5 neprotonovanih 2-alkil-hinona i povećana elektrofilnost položaja 6 u kiseloj sredini, kao i kiselost intermedijernih hidrohinona

Sinteza i karakterizacija nikal(II) i bakar(II) kompleksa sa polidentatnim dialkil ditiokarbaminskim ligandom 3-ditiokarboksi-3-aza-5-aminopentanoatom

Square planar complexes of Ni(II) and Cu(II) with potassium 3-dithiocarboxy-3-aza-5-aminopentanoate have been prepared by direct synthesis. The obtained neutral complexes were characterized by elemental analysis, magnetic susceptibility measurements, infrared and electronic spectra. The thermal behaviour of both the Ni(II) and Cu(II) complexes, and the ligand itself was investigated by DSC and TG.Direktnom sintezom između nikal(II)- i bakar(II)- soli i kalijum 3-ditiokarboksi-3-aza-5-aminopentanoata nagrađeni su odgovarajući kompleksi kvadratno-planarne strukture. Izolovani neutralni kompleksi karakterisani su elementalnom analizom, infracrvenom i elektronskom apsorpcionom spektroskopijom, kao i merenjem magnetnih susceptibiliteta. Termičko ponašanje kompleksa i liganda ispitivano je primenom DSC i TG metoda

Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies

Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.Related to published version:[https://imagine.imgge.bg.ac.rs/handle/123456789/1168]This is the peer reviewed version of the paper: Jakovljević, K., Joksović, M. D., Matić, I., Petrović, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Trifunović, S., & Marković, V. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: Synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. Medchemcomm, 9(10), 1679–1697. [https://doi.org/10.1039/c8md00316e

Supplementary data for the article: Stojković, D. L. J.; Bacchi, A.; Capucci, D.; Milenković, M. R.; Čobeljić, B.; Trifunović, S. R.; Andelković, K.; Jevtić, V. V.; Vuković, N.; Vukić, M.; et al. Synthesis and Characterization of Palladium(II) Complexes with Glycine Coumarin Derivatives. Journal of the Serbian Chemical Society 2016, 81 (12), 1383–1392. https://doi.org/10.2298/JSC160915087S

Supplementary material for: [https://doi.org/10.2298/JSC160915087S]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2392

Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071

Supplementary material for: [https://doi.org/10.1016/j.ejmech.2013.03.071]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1370

Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697. https://doi.org/10.1039/c8md00316e

Supplementary material for: [https://pubs.rsc.org/en/content/articlelanding/2018/MD/C8MD00316E#!divAbstract]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2089]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/2892

Synthesis and characterization of palladium(II) complexes with glycine coumarin derivatives

A Pd(II) complex with methyl 2-([1-{2,4-dioxochroman-3-ylidene}ethyl]amino)acetate was synthesized. The structures of both the ligand and its Pd(II) complex were determined by elemental analysis, and IR and NMR spectroscopy. Recrystallization of the Pd(II) complex from DMF/water solution resulted in its hydrolysis and the formation of the dimethylamine (2-[{1-(2,4-dioxochroman-3-ylidene) ethyl} amino] acetato) palladium(II) complex, the structure of which was determined by elemental analysis, IR, H-1- and C-13-NMR spectroscopy and X-ray analysis.Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3626

Supplementary data for article: Marković, V.; Janićijević, A.; Stanojković, T.; Kolundzija, B.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Djurdjevic, P. T.; Todorović, N.; et al. Synthesis, Cytotoxic Activity and DNA-Interaction Studies of Novel Anthraquinone-Thiosemicarbazones with Tautomerizable Methylene Group. European Journal of Medicinal Chemistry 2013, 64, 228–238. https://doi.org/10.1016/j.ejmech.2013.03.071

Supplementary material for: [https://doi.org/10.1016/j.ejmech.2013.03.071]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1370

Supplementary data for the article: Stojković, D. L. J.; Bacchi, A.; Capucci, D.; Milenković, M. R.; Čobeljić, B.; Trifunović, S. R.; Andelković, K.; Jevtić, V. V.; Vuković, N.; Vukić, M.; et al. Synthesis and Characterization of Palladium(II) Complexes with Glycine Coumarin Derivatives. Journal of the Serbian Chemical Society 2016, 81 (12), 1383–1392. https://doi.org/10.2298/JSC160915087S

Supplementary material for: [https://doi.org/10.2298/JSC160915087S]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2392