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Pregled bibliografske jedinice broj: 630602

N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study


Meščić, Andrijana; Glavač, Danijel; Osmanović, Amar; Završnik, Davorka; Cetina, Mario; Makuc, Damjan; Plavec, Janez; Ametamey, Simon M.; Raić-Malić, Silvana
N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study // Journal of molecular structure, 1039 (2013), 160-166 doi:10.1016/j.molstruc.2013.02.010 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 630602 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study

Autori
Meščić, Andrijana ; Glavač, Danijel ; Osmanović, Amar ; Završnik, Davorka ; Cetina, Mario ; Makuc, Damjan ; Plavec, Janez ; Ametamey, Simon M. ; Raić-Malić, Silvana

Izvornik
Journal of molecular structure (0022-2860) 1039 (2013); 160-166

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
N-acyclic and O-acyclic pyrimidine nucleoside analogs ; NMR ; regioisomers ; self-assembling ; X-ray diffraction

Sažetak
Synthesis of novel 5-(2-hydroxyethyl) and 5-(3-hydroxypropyl) acyclic pyrimidine nucleosides is described. Introduction of penciclovir-like side chain in C-5 substituted pyrimidines occurred both at N-1 and O-2 position of pyrimidine moiety that was corroborated by correlation of signals in 2D HMBC spectra. Therefore, alkylation of 5-(acetoxyethyl)-4-methoxypyrimidin-2-one (2a) and 5-(acetoxypropyl)-4-methoxypyrimidin-2-one (2b) afforded mixture of N- and O-acyclic pyrimidine nucleosides in the ratio of 49: 45 (4a: 5a) and 41: 21 (4b: 5b). Structures of 5-(acetoxyalkyl)-4-methoxypyrimidin-2-ones, as the first examples of 4-methoxypyrimidin-2-ones, were unambiguously confirmed by single crystal X-ray diffraction analysis.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekti:
125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Raić-Malić, Silvana, MZOS ) ( POIROT)

Ustanove:
Tekstilno-tehnološki fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Citiraj ovu publikaciju

Meščić, Andrijana; Glavač, Danijel; Osmanović, Amar; Završnik, Davorka; Cetina, Mario; Makuc, Damjan; Plavec, Janez; Ametamey, Simon M.; Raić-Malić, Silvana
N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study // Journal of molecular structure, 1039 (2013), 160-166 doi:10.1016/j.molstruc.2013.02.010 (međunarodna recenzija, članak, znanstveni)
Meščić, A., Glavač, D., Osmanović, A., Završnik, D., Cetina, M., Makuc, D., Plavec, J., Ametamey, S. & Raić-Malić, S. (2013) N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study. Journal of molecular structure, 1039, 160-166 doi:10.1016/j.molstruc.2013.02.010.
@article{article, year = {2013}, pages = {160-166}, DOI = {10.1016/j.molstruc.2013.02.010}, keywords = {N-acyclic and O-acyclic pyrimidine nucleoside analogs, NMR, regioisomers, self-assembling, X-ray diffraction}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2013.02.010}, volume = {1039}, issn = {0022-2860}, title = {N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study}, keyword = {N-acyclic and O-acyclic pyrimidine nucleoside analogs, NMR, regioisomers, self-assembling, X-ray diffraction} }
@article{article, year = {2013}, pages = {160-166}, DOI = {10.1016/j.molstruc.2013.02.010}, keywords = {N-acyclic and O-acyclic pyrimidine nucleoside analogs, NMR, regioisomers, self-assembling, X-ray diffraction}, journal = {Journal of molecular structure}, doi = {10.1016/j.molstruc.2013.02.010}, volume = {1039}, issn = {0022-2860}, title = {N-alkylated and O-alkylated regioisomers of 5-(hydroxyalkyl)pyrimidines : Synthesis and structural study}, keyword = {N-acyclic and O-acyclic pyrimidine nucleoside analogs, NMR, regioisomers, self-assembling, X-ray diffraction} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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