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Pregled bibliografske jedinice broj: 516150

Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives

Krištafor, Svjetlana; Meščić, Andrijana; Cetina, Mario; Korunda, Silvija; Makuc, Damjan; Plavec, Janez; Raić-Malić, Silvana
Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives // Journal of fluorine chemistry, 132 (2011), 9; 573-578 doi:10.1016/j.jfluchem.2011.06.002 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 516150 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives

Autori
Krištafor, Svjetlana ; Meščić, Andrijana ; Cetina, Mario ; Korunda, Silvija ; Makuc, Damjan ; Plavec, Janez ; Raić-Malić, Silvana

Izvornik
Journal of fluorine chemistry (0022-1139) 132 (2011), 9; 573-578

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

Ključne riječi
mono- and difluorinated N-methyl thymine derivatives ; C-6 unsaturated side-chain ; Z- and E-isomers ; NMR conformational analysis ; positron emission tomography (PET)

Sažetak
A new series of conformationally restricted pyrimidine derivatives bearing C-6 isobutenyl side-chain (2–9) has been prepared. The novel fluoroalkenyl pyrimidine nucleoside mimetic 3 as model compound for development of tracer molecule in positron emission tomography (PET) was synthesized by fluorination reaction of methoxytritylated pyrimidine derivative using diethylaminosulfur trifluoride (DAST). Conversion of one hydroxyl group to methoxytritylated, fluorinated, mesylated and acetylated pyrimidine derivatives (2, 3, 5–7 and 9) afforded a mixture of Z- and E-isomers in which Z-isomers were predominant. Conformational study of 1, and its fluorinated structural congeners 3 and 4 by the use of NOE experiments revealed predominant conformation of compounds where vinyl H-10 proton is spatially close to N-1 methyl and H-30b methylene protons and on the other hand H-30a methylene protons are close to C-5 methyl protons. The stereostructure of 1, 3-dihydroxyisobutenyl N- methyl thymine 1 was unambiguously confirmed by X- ray crystal structure analysis.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA

Projekti:
MZOS-119-1193079-3069 - Novi organski i koordinacijski spojevi - sinteza i suodnos struktura-svojstvo (Kaitner, Branko, MZOS ) ( CroRIS)
MZOS-125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Raić-Malić, Silvana, MZOS ) ( CroRIS)

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

Profili:

Avatar Url Svjetlana Krištafor (autor)

Avatar Url Silvana Raić-Malić (autor)

Avatar Url Andrijana Meščić Macan (autor)

Avatar Url Silvija Maračić (autor)

Avatar Url Mario Cetina (autor)

Poveznice na cjeloviti tekst rada:

doi www.sciencedirect.com dx.doi.org

Citiraj ovu publikaciju:

Krištafor, Svjetlana; Meščić, Andrijana; Cetina, Mario; Korunda, Silvija; Makuc, Damjan; Plavec, Janez; Raić-Malić, Silvana
Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives // Journal of fluorine chemistry, 132 (2011), 9; 573-578 doi:10.1016/j.jfluchem.2011.06.002 (međunarodna recenzija, članak, znanstveni)
Krištafor, S., Meščić, A., Cetina, M., Korunda, S., Makuc, D., Plavec, J. & Raić-Malić, S. (2011) Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives. Journal of fluorine chemistry, 132 (9), 573-578 doi:10.1016/j.jfluchem.2011.06.002.
@article{article, author = {Kri\v{s}tafor, Svjetlana and Me\v{s}\v{c}i\'{c}, Andrijana and Cetina, Mario and Korunda, Silvija and Makuc, Damjan and Plavec, Janez and Rai\'{c}-Mali\'{c}, Silvana}, year = {2011}, pages = {573-578}, DOI = {10.1016/j.jfluchem.2011.06.002}, keywords = {mono- and difluorinated N-methyl thymine derivatives, C-6 unsaturated side-chain, Z- and E-isomers, NMR conformational analysis, positron emission tomography (PET)}, journal = {Journal of fluorine chemistry}, doi = {10.1016/j.jfluchem.2011.06.002}, volume = {132}, number = {9}, issn = {0022-1139}, title = {Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives}, keyword = {mono- and difluorinated N-methyl thymine derivatives, C-6 unsaturated side-chain, Z- and E-isomers, NMR conformational analysis, positron emission tomography (PET)} }
@article{article, author = {Kri\v{s}tafor, Svjetlana and Me\v{s}\v{c}i\'{c}, Andrijana and Cetina, Mario and Korunda, Silvija and Makuc, Damjan and Plavec, Janez and Rai\'{c}-Mali\'{c}, Silvana}, year = {2011}, pages = {573-578}, DOI = {10.1016/j.jfluchem.2011.06.002}, keywords = {mono- and difluorinated N-methyl thymine derivatives, C-6 unsaturated side-chain, Z- and E-isomers, NMR conformational analysis, positron emission tomography (PET)}, journal = {Journal of fluorine chemistry}, doi = {10.1016/j.jfluchem.2011.06.002}, volume = {132}, number = {9}, issn = {0022-1139}, title = {Synthesis, structural and conformational studies of Z- and E-isomers of fluorinated C-6 isobutenyl N-methyl thymine derivatives}, keyword = {mono- and difluorinated N-methyl thymine derivatives, C-6 unsaturated side-chain, Z- and E-isomers, NMR conformational analysis, positron emission tomography (PET)} }

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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