TY  - JOUR
AU  - Stepanović-Petrović, Radica
AU  - Tokić-Vujošević, Zorana
AU  - Milovanović, S
AU  - Ceković, Z
AU  - Tomić, Maja
PY  - 2004
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/476
AB  - The transformation of isosorbide-5-mononitrate (CAS 16051-77-7, IS-5-MN) to the corresponding keto derivative and its ketoxime (oxime-nitrate derivative of isosorbide) is described. The effects of IS-5-MN and the new oxime-nitrate (ON) on the endothelial and smooth muscle cells of isolated rings of the rat superior mesenteric artery were examined. After contraction induced by phenylephrine, IS-5-MN (10(-8)-10(-4) mol/1) caused a concentration-dependent relaxation. Removal of the vascular endothelium strongly potentiated this effect. On the other hand, the new ON (10(-8)-10(-4) mol/1) was a more potent relaxant than the parent drug, but its effect was not dependent on the vascular endothelium. The inhibitory effect of the artery without endothelium to the new ON was more pronounced than that to IS-5-MN. The mechanism of the relaxant effect of the new compound consisted in the liberation of nitric-oxide (NO) which activated guanylate cyclase (GC), upon which accumulation of cyclic guanosine monophosphate (cGMP) occurred, which was the second messenger leading to relaxation. Tolerance to the frequent applications of the new compound was not observed, moreover a slight increase of the effect was detected in comparison with IS-5-MN for which tolerance was observed to a great extent. Clinically, the new ON could be favorable in all types of angina in comparison with the classical IS-5-MN.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Arzneimittelforschung - Drug Research
T1  - Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug
VL  - 54
IS  - 4
SP  - 195
EP  - 202
DO  - 10.1055/s-0031-1296959
UR  - https://hdl.handle.net/21.15107/rcub_farfar_476
ER  - 

@article{
author = "Stepanović-Petrović, Radica and Tokić-Vujošević, Zorana and Milovanović, S and Ceković, Z and Tomić, Maja",
year = "2004",
abstract = "The transformation of isosorbide-5-mononitrate (CAS 16051-77-7, IS-5-MN) to the corresponding keto derivative and its ketoxime (oxime-nitrate derivative of isosorbide) is described. The effects of IS-5-MN and the new oxime-nitrate (ON) on the endothelial and smooth muscle cells of isolated rings of the rat superior mesenteric artery were examined. After contraction induced by phenylephrine, IS-5-MN (10(-8)-10(-4) mol/1) caused a concentration-dependent relaxation. Removal of the vascular endothelium strongly potentiated this effect. On the other hand, the new ON (10(-8)-10(-4) mol/1) was a more potent relaxant than the parent drug, but its effect was not dependent on the vascular endothelium. The inhibitory effect of the artery without endothelium to the new ON was more pronounced than that to IS-5-MN. The mechanism of the relaxant effect of the new compound consisted in the liberation of nitric-oxide (NO) which activated guanylate cyclase (GC), upon which accumulation of cyclic guanosine monophosphate (cGMP) occurred, which was the second messenger leading to relaxation. Tolerance to the frequent applications of the new compound was not observed, moreover a slight increase of the effect was detected in comparison with IS-5-MN for which tolerance was observed to a great extent. Clinically, the new ON could be favorable in all types of angina in comparison with the classical IS-5-MN.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Arzneimittelforschung - Drug Research",
title = "Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug",
volume = "54",
number = "4",
pages = "195-202",
doi = "10.1055/s-0031-1296959",
url = "https://hdl.handle.net/21.15107/rcub_farfar_476"
}

Stepanović-Petrović, R., Tokić-Vujošević, Z., Milovanović, S., Ceković, Z.,& Tomić, M.. (2004). Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug. in Arzneimittelforschung - Drug Research
Georg Thieme Verlag Kg, Stuttgart., 54(4), 195-202.
https://doi.org/10.1055/s-0031-1296959
https://hdl.handle.net/21.15107/rcub_farfar_476

Stepanović-Petrović R, Tokić-Vujošević Z, Milovanović S, Ceković Z, Tomić M. Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug. in Arzneimittelforschung - Drug Research. 2004;54(4):195-202.
doi:10.1055/s-0031-1296959
https://hdl.handle.net/21.15107/rcub_farfar_476 .

Stepanović-Petrović, Radica, Tokić-Vujošević, Zorana, Milovanović, S, Ceković, Z, Tomić, Maja, "Comparison of the relaxant effects of a new oxime-nitrate derived from isosorbide-5-mononitrate and the parent drug" in Arzneimittelforschung - Drug Research, 54, no. 4 (2004):195-202,
https://doi.org/10.1055/s-0031-1296959 .,
https://hdl.handle.net/21.15107/rcub_farfar_476 .

TY  - JOUR
AU  - Petrović, RMS
AU  - Tokić-Vujošević, Zorana
AU  - Milovanov, S
AU  - Ceković, Z
AU  - Bokonjić, Dubravko
AU  - Dobrić, Silva
PY  - 2002
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/322
PB  - Govi-Verlag Gmbh, Eschborn
T2  - Pharmazie
T1  - Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery
VL  - 57
IS  - 7
SP  - 507
EP  - 508
UR  - https://hdl.handle.net/21.15107/rcub_farfar_322
ER  - 

@article{
author = "Petrović, RMS and Tokić-Vujošević, Zorana and Milovanov, S and Ceković, Z and Bokonjić, Dubravko and Dobrić, Silva",
year = "2002",
publisher = "Govi-Verlag Gmbh, Eschborn",
journal = "Pharmazie",
title = "Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery",
volume = "57",
number = "7",
pages = "507-508",
url = "https://hdl.handle.net/21.15107/rcub_farfar_322"
}

Petrović, R., Tokić-Vujošević, Z., Milovanov, S., Ceković, Z., Bokonjić, D.,& Dobrić, S.. (2002). Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery. in Pharmazie
Govi-Verlag Gmbh, Eschborn., 57(7), 507-508.
https://hdl.handle.net/21.15107/rcub_farfar_322

Petrović R, Tokić-Vujošević Z, Milovanov S, Ceković Z, Bokonjić D, Dobrić S. Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery. in Pharmazie. 2002;57(7):507-508.
https://hdl.handle.net/21.15107/rcub_farfar_322 .

Petrović, RMS, Tokić-Vujošević, Zorana, Milovanov, S, Ceković, Z, Bokonjić, Dubravko, Dobrić, Silva, "Pharmacological evaluation of a novel oxime derived from isosorbide-5-mononitrate on isolated rat superior mesenteric artery" in Pharmazie, 57, no. 7 (2002):507-508,
https://hdl.handle.net/21.15107/rcub_farfar_322 .

TY  - JOUR
AU  - Tokić-Vujošević, Zorana
AU  - Ceković, Z
PY  - 2001
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/303
AB  - The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.
PB  - Georg Thieme Verlag
T2  - Synthesis
T1  - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives
IS  - 13
SP  - 2028
EP  - 2034
DO  - 10.1055/s-2001-17705
ER  - 

@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
abstract = "The synthesis of the diastereomeric nitrate esters (3R,4R)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (5b) and (3R,4S)-(2-hydroxy-4-nitrooxytetrahydrofuran-3-yloxy)acetonitrile (9) was achieved by the Beckmann fragmentation of 1,4:3,6-dianhydro-D-glucitol-5-(or -2-)nitrate-2-(or -5-)ketoximes (4b and 8), respectively. The bicyclic delta -lactams, (1R,6R,7R)-N-methyl-7-endo-nitrooxy-3-oxo-5,9-dioxa-2-azabicy-clo[4.3.0]nonane (15b) and the stereoisomer (1R,6R,7S)-7-exo-nitrooxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18b) were prepared by the Beckmann rearrangement of nitrones 14b and 17b, respectively. The stereoisomeric delta -lactams, N-methyl-7-endo-benzoyloxy- (15a) and N-methyl-7-exo-benzoyloxy-3-oxo-5,9-dioxa-2-azabicyclo[4.3.0]nonane (18a) were prepared from the corresponding nitrones 14a and 17a, respectively.",
publisher = "Georg Thieme Verlag",
journal = "Synthesis",
title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives",
number = "13",
pages = "2028-2034",
doi = "10.1055/s-2001-17705"
}

Tokić-Vujošević, Z.,& Ceković, Z.. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. in Synthesis
Georg Thieme Verlag.(13), 2028-2034.
https://doi.org/10.1055/s-2001-17705

Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives. in Synthesis. 2001;(13):2028-2034.
doi:10.1055/s-2001-17705 .

Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrate II: Bicyclic delta-lactams and tetrahydrofuran derivatives" in Synthesis, no. 13 (2001):2028-2034,
https://doi.org/10.1055/s-2001-17705 . .

TY  - JOUR
AU  - Tokić-Vujošević, Zorana
AU  - Ceković, Z
PY  - 2001
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/289
AB  - A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.
PB  - Freund Publishing House Ltd, London
T2  - Heterocyclic Communications
T1  - Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates
VL  - 7
IS  - 1
SP  - 43
EP  - 48
UR  - https://hdl.handle.net/21.15107/rcub_farfar_289
ER  - 

@article{
author = "Tokić-Vujošević, Zorana and Ceković, Z",
year = "2001",
abstract = "A synthesis of diastereomeric (7R) 7-endo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0]nonane (4b) and (7S) 7-exo-nitrooxy-3-oxo-2,5,9-trioxabicyclo[4.3.0] (7b) is described using D-glucitol as a starting compound. Bicyclic delta -lactones 4 and 7 are obtained in the reaction of 1,4-3,6-dianhydro-2-keto-D-glucitol-5-acylates 3 and 1,4-3, 6-dianhydro-5-keto-D-glucitol-2-acylates 6 with m-chloroperbenzoic acid. Hydrolysis of lactones 4b and 7b and subsequent esterification afforded the corresponding stereoisomeric (3R,4R) methyl (2-acetoxy-4-nitrooxytetrahydrofuran-3-yloxy)-acetate 10 and (3R,4S) isomer 12, respectively.",
publisher = "Freund Publishing House Ltd, London",
journal = "Heterocyclic Communications",
title = "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates",
volume = "7",
number = "1",
pages = "43-48",
url = "https://hdl.handle.net/21.15107/rcub_farfar_289"
}

Tokić-Vujošević, Z.,& Ceković, Z.. (2001). Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications
Freund Publishing House Ltd, London., 7(1), 43-48.
https://hdl.handle.net/21.15107/rcub_farfar_289

Tokić-Vujošević Z, Ceković Z. Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates. in Heterocyclic Communications. 2001;7(1):43-48.
https://hdl.handle.net/21.15107/rcub_farfar_289 .

Tokić-Vujošević, Zorana, Ceković, Z, "Synthesis of new stereoisomeric nitrate esters derived from isosorbide-mononitrates" in Heterocyclic Communications, 7, no. 1 (2001):43-48,
https://hdl.handle.net/21.15107/rcub_farfar_289 .