TY  - JOUR
AU  - Damljanovic, Ivan
AU  - Vukicevic, Mirjana
AU  - Manojlović, Dragan D.
AU  - Šojić, Nešo
AU  - Buriez, Olivier
AU  - Vukicevic, Rastko D.
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1042
AB  - The electrochemical bromination of 3,4.6-tri-O-acetyl-D-glucal (1) has been investigated in dimethyl sulfoxide (DMSO) by cyclic voltammetry and preparative-scale electrolyses. In this solvent, the bromination involves a bromine-DMSO complex of the type [DMSO-Br](+) Br(-) whose reactivity towards 1 was clearly evidenced by cyclic voltammetry. Importantly, only the monobrominated glucose and mannose derivatives were obtained from electrolyses. This specific behavior was attributed to the nucleophilicity of DMSO that may react with the oxocarbenium intermediate preventing thus a possible second bromination of the transient species. The gluco/manno ratio, roughly equal to 30/70, indicated an electrophilic attack by [DMSO-Br](+) Br(-) preferentially from the beta side of the starting glycal for steric reasons. The treatment of the crude product obtained after the end of the electrolyses with acetic anhydride allowed the preparation of derivatives in which the anomeric carbon bears an acetoxy group. Based on both the cyclic voltammetry experiments and preparative-scale electrolyses, a mechanism is proposed for the bromination of peracetylated D-glucal in DMSO. These new and original results are of high interest in carbohydrate chemistry and especially for the preparation of new valuable oligosaccharides. (C) 2009 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Electrochimica Acta
T1  - Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity
VL  - 55
IS  - 3
SP  - 965
EP  - 969
DO  - 10.1016/j.electacta.2009.09.057
ER  - 

@article{
author = "Damljanovic, Ivan and Vukicevic, Mirjana and Manojlović, Dragan D. and Šojić, Nešo and Buriez, Olivier and Vukicevic, Rastko D.",
year = "2010",
abstract = "The electrochemical bromination of 3,4.6-tri-O-acetyl-D-glucal (1) has been investigated in dimethyl sulfoxide (DMSO) by cyclic voltammetry and preparative-scale electrolyses. In this solvent, the bromination involves a bromine-DMSO complex of the type [DMSO-Br](+) Br(-) whose reactivity towards 1 was clearly evidenced by cyclic voltammetry. Importantly, only the monobrominated glucose and mannose derivatives were obtained from electrolyses. This specific behavior was attributed to the nucleophilicity of DMSO that may react with the oxocarbenium intermediate preventing thus a possible second bromination of the transient species. The gluco/manno ratio, roughly equal to 30/70, indicated an electrophilic attack by [DMSO-Br](+) Br(-) preferentially from the beta side of the starting glycal for steric reasons. The treatment of the crude product obtained after the end of the electrolyses with acetic anhydride allowed the preparation of derivatives in which the anomeric carbon bears an acetoxy group. Based on both the cyclic voltammetry experiments and preparative-scale electrolyses, a mechanism is proposed for the bromination of peracetylated D-glucal in DMSO. These new and original results are of high interest in carbohydrate chemistry and especially for the preparation of new valuable oligosaccharides. (C) 2009 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Electrochimica Acta",
title = "Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity",
volume = "55",
number = "3",
pages = "965-969",
doi = "10.1016/j.electacta.2009.09.057"
}

Damljanovic, I., Vukicevic, M., Manojlović, D. D., Šojić, N., Buriez, O.,& Vukicevic, R. D.. (2010). Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity. in Electrochimica Acta
Pergamon-Elsevier Science Ltd, Oxford., 55(3), 965-969.
https://doi.org/10.1016/j.electacta.2009.09.057

Damljanovic I, Vukicevic M, Manojlović DD, Šojić N, Buriez O, Vukicevic RD. Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity. in Electrochimica Acta. 2010;55(3):965-969.
doi:10.1016/j.electacta.2009.09.057 .

Damljanovic, Ivan, Vukicevic, Mirjana, Manojlović, Dragan D., Šojić, Nešo, Buriez, Olivier, Vukicevic, Rastko D., "Electrochemical bromination of peracetylated D-glucal: Effect of DMSO on chemoselectivity" in Electrochimica Acta, 55, no. 3 (2010):965-969,
https://doi.org/10.1016/j.electacta.2009.09.057 . .

TY  - JOUR
AU  - Damljanovic, Ivan
AU  - Colovic, Marija
AU  - Vukicevic, Mirjana
AU  - Manojlović, Dragan D.
AU  - Radulović, Niko S.
AU  - Wurst, Klaus
AU  - Laus, Gerhard
AU  - Ratkovic, Zoran
AU  - Joksović, Milan D.
AU  - Vukicevic, Rastko D.
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/618
AB  - New ferrocene derivatives - 1H-1-phenylpyrazole-4-carboxaldehydes containing o-, m- and p- ferrocenylphenyl group at position 3 - were synthesized and characterized. The electrochemical investigation showed that the position of the ferrocenyl group does not affect the redox potential of these compounds. The X-ray crystal structure of the ortho-derivative is also presented. The screening for the in vitro antimicrobial activity against eleven bacterial and three fungal/yeast strains exhibited complete inactivity of these aldehydes, but n-butyl imines of ortho and meta derivatives showed moderate activity compared to those of the used standards. (C) 2009 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Sa, Lausanne
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes
VL  - 694
IS  - 9-10
SP  - 1575
EP  - 1580
DO  - 10.1016/j.jorganchem.2009.01.045
ER  - 

@article{
author = "Damljanovic, Ivan and Colovic, Marija and Vukicevic, Mirjana and Manojlović, Dragan D. and Radulović, Niko S. and Wurst, Klaus and Laus, Gerhard and Ratkovic, Zoran and Joksović, Milan D. and Vukicevic, Rastko D.",
year = "2009",
abstract = "New ferrocene derivatives - 1H-1-phenylpyrazole-4-carboxaldehydes containing o-, m- and p- ferrocenylphenyl group at position 3 - were synthesized and characterized. The electrochemical investigation showed that the position of the ferrocenyl group does not affect the redox potential of these compounds. The X-ray crystal structure of the ortho-derivative is also presented. The screening for the in vitro antimicrobial activity against eleven bacterial and three fungal/yeast strains exhibited complete inactivity of these aldehydes, but n-butyl imines of ortho and meta derivatives showed moderate activity compared to those of the used standards. (C) 2009 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes",
volume = "694",
number = "9-10",
pages = "1575-1580",
doi = "10.1016/j.jorganchem.2009.01.045"
}

Damljanovic, I., Colovic, M., Vukicevic, M., Manojlović, D. D., Radulović, N. S., Wurst, K., Laus, G., Ratkovic, Z., Joksović, M. D.,& Vukicevic, R. D.. (2009). Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes. in Journal of Organometallic Chemistry
Elsevier Science Sa, Lausanne., 694(9-10), 1575-1580.
https://doi.org/10.1016/j.jorganchem.2009.01.045

Damljanovic I, Colovic M, Vukicevic M, Manojlović DD, Radulović NS, Wurst K, Laus G, Ratkovic Z, Joksović MD, Vukicevic RD. Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes. in Journal of Organometallic Chemistry. 2009;694(9-10):1575-1580.
doi:10.1016/j.jorganchem.2009.01.045 .

Damljanovic, Ivan, Colovic, Marija, Vukicevic, Mirjana, Manojlović, Dragan D., Radulović, Niko S., Wurst, Klaus, Laus, Gerhard, Ratkovic, Zoran, Joksović, Milan D., Vukicevic, Rastko D., "Synthesis, spectral characterization and electrochemical properties of 1H-3-(o-, m- and p-ferrocenylphenyl)-1-phenylpyrazole-4-carboxaldehydes" in Journal of Organometallic Chemistry, 694, no. 9-10 (2009):1575-1580,
https://doi.org/10.1016/j.jorganchem.2009.01.045 . .

TY  - JOUR
AU  - Joksović, Milan D.
AU  - Marković, Violeta
AU  - Juranić, Zorica D.
AU  - Stanojković, Tatjana
AU  - Jovanović, Ljiljana S.
AU  - Damljanovic, Ivan S.
AU  - Szecsenyi, Katalin Meszaros
AU  - Todorović, Nina
AU  - Trifunović, Snežana S.
AU  - Vukicevic, Rastko D.
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1024
AB  - A series of new N-[(3-ferrocenyl-1-phenylpyrazol-4-yl)methyl] alpha-amino acids were prepared and characterized by a range of spectroscopic techniques and cyclic voltammetry. The in vitro antitumor activity of all synthesized compounds was investigated against cervix adenocarcinoma HeLa, melanoma Fem-x and myelogenous leukemia K562 cell lines using the MTT method. Tryptophan derivative 11 exhibited the highest cytotoxic activity in the cell growth inhibition of all three types of cell lines. (C) 2009 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Sa, Lausanne
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, characterization and antitumor activity of novel N-substituted alpha-amino acids containing ferrocenyl pyrazole-moiety
VL  - 694
IS  - 24
SP  - 3935
EP  - 3942
DO  - 10.1016/j.jorganchem.2009.08.013
ER  - 

@article{
author = "Joksović, Milan D. and Marković, Violeta and Juranić, Zorica D. and Stanojković, Tatjana and Jovanović, Ljiljana S. and Damljanovic, Ivan S. and Szecsenyi, Katalin Meszaros and Todorović, Nina and Trifunović, Snežana S. and Vukicevic, Rastko D.",
year = "2009",
abstract = "A series of new N-[(3-ferrocenyl-1-phenylpyrazol-4-yl)methyl] alpha-amino acids were prepared and characterized by a range of spectroscopic techniques and cyclic voltammetry. The in vitro antitumor activity of all synthesized compounds was investigated against cervix adenocarcinoma HeLa, melanoma Fem-x and myelogenous leukemia K562 cell lines using the MTT method. Tryptophan derivative 11 exhibited the highest cytotoxic activity in the cell growth inhibition of all three types of cell lines. (C) 2009 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, characterization and antitumor activity of novel N-substituted alpha-amino acids containing ferrocenyl pyrazole-moiety",
volume = "694",
number = "24",
pages = "3935-3942",
doi = "10.1016/j.jorganchem.2009.08.013"
}

Joksović, M. D., Marković, V., Juranić, Z. D., Stanojković, T., Jovanović, L. S., Damljanovic, I. S., Szecsenyi, K. M., Todorović, N., Trifunović, S. S.,& Vukicevic, R. D.. (2009). Synthesis, characterization and antitumor activity of novel N-substituted alpha-amino acids containing ferrocenyl pyrazole-moiety. in Journal of Organometallic Chemistry
Elsevier Science Sa, Lausanne., 694(24), 3935-3942.
https://doi.org/10.1016/j.jorganchem.2009.08.013

Joksović MD, Marković V, Juranić ZD, Stanojković T, Jovanović LS, Damljanovic IS, Szecsenyi KM, Todorović N, Trifunović SS, Vukicevic RD. Synthesis, characterization and antitumor activity of novel N-substituted alpha-amino acids containing ferrocenyl pyrazole-moiety. in Journal of Organometallic Chemistry. 2009;694(24):3935-3942.
doi:10.1016/j.jorganchem.2009.08.013 .

Joksović, Milan D., Marković, Violeta, Juranić, Zorica D., Stanojković, Tatjana, Jovanović, Ljiljana S., Damljanovic, Ivan S., Szecsenyi, Katalin Meszaros, Todorović, Nina, Trifunović, Snežana S., Vukicevic, Rastko D., "Synthesis, characterization and antitumor activity of novel N-substituted alpha-amino acids containing ferrocenyl pyrazole-moiety" in Journal of Organometallic Chemistry, 694, no. 24 (2009):3935-3942,
https://doi.org/10.1016/j.jorganchem.2009.08.013 . .