TY  - JOUR
AU  - Salihovic, Mirsada
AU  - Osmanović, Amar
AU  - Špirtović-Halilović, Selma
AU  - Roca, Sunčica
AU  - Meščić, Andrijana
AU  - Vujisić, Ljubodrag V.
AU  - Trifunović, Snežana S.
AU  - Završnik, Davorka
AU  - Sofić, Emin
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3448
AB  - Because of the great pharmacological potential of the pyrimidine motif, novel C-5 substituted N-3 acyclic and O-4 acyclic pyrimidine derivatives were prepared as an interesting class of compounds for biological evaluation. Introduction of the 2,3-dihydroxypropyl (DHP) and penciclovir (PCV)-like side chains to 2-methoxypyrimidin-4-one (2) afforded a mixture of N- and O-acyclic pyrimidine nucleosides in the ratio of 54: 29 (3:4) and 57:21 (5:6) with N-3 isomer being dominant. Distinction between N- and O-alkylated pyrimidine moiety was deduced from extensive experimental FT-IR, HPLC-MS and 1D (H-1, C-13) and 2D (COSY, HMQC and HMBC) NMR analyses. The N-, O-regioisomers were also examined by computational method at density functional theory (DFT) RB3LYP/6-31G(d), 6-31G** and 6-31+G* levels. DFT global chemical reactivity descriptors (total energy, chemical hardness, electronic chemical potential and electrophilicity) were calculated for the isomers and used to predict and describe their relative stability and reactivity. The chemical reactivity indices were related to the C-2-N-3-C-4 bond angle. Theoretical predictions can be used to compare chemical reactivity and stability with future biological evaluation and behaviour of these compounds.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine
VL  - 1091
SP  - 170
EP  - 176
DO  - 10.1016/j.molstruc.2015.02.078
ER  - 

@article{
author = "Salihovic, Mirsada and Osmanović, Amar and Špirtović-Halilović, Selma and Roca, Sunčica and Meščić, Andrijana and Vujisić, Ljubodrag V. and Trifunović, Snežana S. and Završnik, Davorka and Sofić, Emin",
year = "2015",
abstract = "Because of the great pharmacological potential of the pyrimidine motif, novel C-5 substituted N-3 acyclic and O-4 acyclic pyrimidine derivatives were prepared as an interesting class of compounds for biological evaluation. Introduction of the 2,3-dihydroxypropyl (DHP) and penciclovir (PCV)-like side chains to 2-methoxypyrimidin-4-one (2) afforded a mixture of N- and O-acyclic pyrimidine nucleosides in the ratio of 54: 29 (3:4) and 57:21 (5:6) with N-3 isomer being dominant. Distinction between N- and O-alkylated pyrimidine moiety was deduced from extensive experimental FT-IR, HPLC-MS and 1D (H-1, C-13) and 2D (COSY, HMQC and HMBC) NMR analyses. The N-, O-regioisomers were also examined by computational method at density functional theory (DFT) RB3LYP/6-31G(d), 6-31G** and 6-31+G* levels. DFT global chemical reactivity descriptors (total energy, chemical hardness, electronic chemical potential and electrophilicity) were calculated for the isomers and used to predict and describe their relative stability and reactivity. The chemical reactivity indices were related to the C-2-N-3-C-4 bond angle. Theoretical predictions can be used to compare chemical reactivity and stability with future biological evaluation and behaviour of these compounds.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine",
volume = "1091",
pages = "170-176",
doi = "10.1016/j.molstruc.2015.02.078"
}

Salihovic, M., Osmanović, A., Špirtović-Halilović, S., Roca, S., Meščić, A., Vujisić, L. V., Trifunović, S. S., Završnik, D.,& Sofić, E.. (2015). Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 1091, 170-176.
https://doi.org/10.1016/j.molstruc.2015.02.078

Salihovic M, Osmanović A, Špirtović-Halilović S, Roca S, Meščić A, Vujisić LV, Trifunović SS, Završnik D, Sofić E. Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine. in Journal of Molecular Structure. 2015;1091:170-176.
doi:10.1016/j.molstruc.2015.02.078 .

Salihovic, Mirsada, Osmanović, Amar, Špirtović-Halilović, Selma, Roca, Sunčica, Meščić, Andrijana, Vujisić, Ljubodrag V., Trifunović, Snežana S., Završnik, Davorka, Sofić, Emin, "Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine" in Journal of Molecular Structure, 1091 (2015):170-176,
https://doi.org/10.1016/j.molstruc.2015.02.078 . .

TY  - JOUR
AU  - Salihovic, Mirsada
AU  - Osmanović, Amar
AU  - Špirtović-Halilović, Selma
AU  - Roca, Sunčica
AU  - Meščić, Andrijana
AU  - Vujisić, Ljubodrag V.
AU  - Trifunović, Snežana S.
AU  - Završnik, Davorka
AU  - Sofić, Emin
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1696
AB  - Because of the great pharmacological potential of the pyrimidine motif, novel C-5 substituted N-3 acyclic and O-4 acyclic pyrimidine derivatives were prepared as an interesting class of compounds for biological evaluation. Introduction of the 2,3-dihydroxypropyl (DHP) and penciclovir (PCV)-like side chains to 2-methoxypyrimidin-4-one (2) afforded a mixture of N- and O-acyclic pyrimidine nucleosides in the ratio of 54: 29 (3:4) and 57:21 (5:6) with N-3 isomer being dominant. Distinction between N- and O-alkylated pyrimidine moiety was deduced from extensive experimental FT-IR, HPLC-MS and 1D (H-1, C-13) and 2D (COSY, HMQC and HMBC) NMR analyses. The N-, O-regioisomers were also examined by computational method at density functional theory (DFT) RB3LYP/6-31G(d), 6-31G** and 6-31+G* levels. DFT global chemical reactivity descriptors (total energy, chemical hardness, electronic chemical potential and electrophilicity) were calculated for the isomers and used to predict and describe their relative stability and reactivity. The chemical reactivity indices were related to the C-2-N-3-C-4 bond angle. Theoretical predictions can be used to compare chemical reactivity and stability with future biological evaluation and behaviour of these compounds.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Molecular Structure
T1  - Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine
VL  - 1091
SP  - 170
EP  - 176
DO  - 10.1016/j.molstruc.2015.02.078
ER  - 

@article{
author = "Salihovic, Mirsada and Osmanović, Amar and Špirtović-Halilović, Selma and Roca, Sunčica and Meščić, Andrijana and Vujisić, Ljubodrag V. and Trifunović, Snežana S. and Završnik, Davorka and Sofić, Emin",
year = "2015",
abstract = "Because of the great pharmacological potential of the pyrimidine motif, novel C-5 substituted N-3 acyclic and O-4 acyclic pyrimidine derivatives were prepared as an interesting class of compounds for biological evaluation. Introduction of the 2,3-dihydroxypropyl (DHP) and penciclovir (PCV)-like side chains to 2-methoxypyrimidin-4-one (2) afforded a mixture of N- and O-acyclic pyrimidine nucleosides in the ratio of 54: 29 (3:4) and 57:21 (5:6) with N-3 isomer being dominant. Distinction between N- and O-alkylated pyrimidine moiety was deduced from extensive experimental FT-IR, HPLC-MS and 1D (H-1, C-13) and 2D (COSY, HMQC and HMBC) NMR analyses. The N-, O-regioisomers were also examined by computational method at density functional theory (DFT) RB3LYP/6-31G(d), 6-31G** and 6-31+G* levels. DFT global chemical reactivity descriptors (total energy, chemical hardness, electronic chemical potential and electrophilicity) were calculated for the isomers and used to predict and describe their relative stability and reactivity. The chemical reactivity indices were related to the C-2-N-3-C-4 bond angle. Theoretical predictions can be used to compare chemical reactivity and stability with future biological evaluation and behaviour of these compounds.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Molecular Structure",
title = "Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine",
volume = "1091",
pages = "170-176",
doi = "10.1016/j.molstruc.2015.02.078"
}

Salihovic, M., Osmanović, A., Špirtović-Halilović, S., Roca, S., Meščić, A., Vujisić, L. V., Trifunović, S. S., Završnik, D.,& Sofić, E.. (2015). Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine. in Journal of Molecular Structure
Elsevier Science Bv, Amsterdam., 1091, 170-176.
https://doi.org/10.1016/j.molstruc.2015.02.078

Salihovic M, Osmanović A, Špirtović-Halilović S, Roca S, Meščić A, Vujisić LV, Trifunović SS, Završnik D, Sofić E. Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine. in Journal of Molecular Structure. 2015;1091:170-176.
doi:10.1016/j.molstruc.2015.02.078 .

Salihovic, Mirsada, Osmanović, Amar, Špirtović-Halilović, Selma, Roca, Sunčica, Meščić, Andrijana, Vujisić, Ljubodrag V., Trifunović, Snežana S., Završnik, Davorka, Sofić, Emin, "Synthesis, structural, conformational and DFT studies of N-3 and O-4 alkylated regioisomers of 5-(hydroxypropyl)pyrimidine" in Journal of Molecular Structure, 1091 (2015):170-176,
https://doi.org/10.1016/j.molstruc.2015.02.078 . .