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Pregled bibliografske jedinice broj: 301146

Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations


Prekupec, Svjetlana; Makuc, Damjan; Plavec, Janez; Šuman, Lidija; Kralj, Marijeta; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen; Raić-Malić, Silvana
Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations // Journal of medicinal chemistry, 50 (2007), 13; 3037-3045 doi:10.1021/jm0614329 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 301146 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations

Autori
Prekupec, Svjetlana ; Makuc, Damjan ; Plavec, Janez ; Šuman, Lidija ; Kralj, Marijeta ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen ; Raić-Malić, Silvana

Izvornik
Journal of medicinal chemistry (0022-2623) 50 (2007), 13; 3037-3045

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

Ključne riječi
fluoroalkylated pyrimidines ; positron-emission tomography ; NMR conformational analysis ; antiviral and cytostatic activity evaluations

Sažetak
The synthetic route for introduction of a fluoroalkyl (7-12, 14), fluoroalkenyl (15 and 16), fluorophenylalkyl (17, 19, 20, and 22), and fluorophenylalkenyl (18, 21) side chain at C-6 of the pyrimidine involved the lithiation of the pyrimidine derivatives 3 and 3a and subsequent nucleophilic addition or substitution reactions of the organolithium intermediate thus obtained with various electrophiles. Conformational properties of the novel fluorinated pyrimidine derivatives were assessed by the use of 1D difference NOE enhancements and C-F coupling constants. Compounds 4-22 were evaluated for their antiviral and cytostatic activities. Of all compounds evaluated, the 5-bromopyrimidine derivatives 5 and 6 showed the highest inhibitory activities. Among the series of fluoroalkylated pyrimidines, which is generally more active than the series of fluorophenylalkylated pyrimidines, compounds 8 and 14 displayed moderate cytostatic activities against the tested tumor cell lines. Moreover, compound 8 containing a 2-fluoromethylpropyl side chain expressed some but not highly specific activity against varicella-zoster virus (VZV). From C-6 fluorophenylalkylated pyrimidine derivatives, 17a and 21 showed a slight activity against cytomegalovirus (CMV), VZV, and Coxsackie B4 virus, respectively. Besides, compounds 17a and 21 showed no cytotoxic effect.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekti:
098-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti
MZOS-098-0982464-2514 - Uloga različitih mehanizama odgovora stanica na terapiju oštećenjem DNA (Kralj, Marijeta, MZOS ) ( POIROT)
MZOS-125-0982464-2922 - RAZVOJ NOVIH PROLIJEKOVA I LIJEKOVA PROTIV VIRUSA I RAKA (Mintas, Mladen, MZOS ) ( POIROT)
MZOS-125-0982464-2925 - Razvoj i primjena novih molekula u pozitron-emisijskoj tomografiji (PET) (Raić-Malić, Silvana, MZOS ) ( POIROT)

Ustanove:
Institut "Ruđer Bošković", Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Poveznice na cjeloviti tekst rada:

doi dx.doi.org pubs.acs.org

Citiraj ovu publikaciju:

Prekupec, Svjetlana; Makuc, Damjan; Plavec, Janez; Šuman, Lidija; Kralj, Marijeta; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen; Raić-Malić, Silvana
Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations // Journal of medicinal chemistry, 50 (2007), 13; 3037-3045 doi:10.1021/jm0614329 (međunarodna recenzija, članak, znanstveni)
Prekupec, S., Makuc, D., Plavec, J., Šuman, L., Kralj, M., Pavelić, K., Balzarini, J., De Clercq, E., Mintas, M. & Raić-Malić, S. (2007) Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations. Journal of medicinal chemistry, 50 (13), 3037-3045 doi:10.1021/jm0614329.
@article{article, author = {Prekupec, Svjetlana and Makuc, Damjan and Plavec, Janez and \v{S}uman, Lidija and Kralj, Marijeta and Paveli\'{c}, Kre\v{s}imir and Balzarini, Jan and De Clercq, Erik and Mintas, Mladen and Rai\'{c}-Mali\'{c}, Silvana}, year = {2007}, pages = {3037-3045}, DOI = {10.1021/jm0614329}, keywords = {fluoroalkylated pyrimidines, positron-emission tomography, NMR conformational analysis, antiviral and cytostatic activity evaluations}, journal = {Journal of medicinal chemistry}, doi = {10.1021/jm0614329}, volume = {50}, number = {13}, issn = {0022-2623}, title = {Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations}, keyword = {fluoroalkylated pyrimidines, positron-emission tomography, NMR conformational analysis, antiviral and cytostatic activity evaluations} }
@article{article, author = {Prekupec, Svjetlana and Makuc, Damjan and Plavec, Janez and \v{S}uman, Lidija and Kralj, Marijeta and Paveli\'{c}, Kre\v{s}imir and Balzarini, Jan and De Clercq, Erik and Mintas, Mladen and Rai\'{c}-Mali\'{c}, Silvana}, year = {2007}, pages = {3037-3045}, DOI = {10.1021/jm0614329}, keywords = {fluoroalkylated pyrimidines, positron-emission tomography, NMR conformational analysis, antiviral and cytostatic activity evaluations}, journal = {Journal of medicinal chemistry}, doi = {10.1021/jm0614329}, volume = {50}, number = {13}, issn = {0022-2623}, title = {Novel C-6 fluorinated acyclic side chain pyrimidine derivatives: Synthesis, H-1 and C-13 NMR conformational studies, and antiviral and cytostatic evaluations}, keyword = {fluoroalkylated pyrimidines, positron-emission tomography, NMR conformational analysis, antiviral and cytostatic activity evaluations} }

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
  • MEDLINE


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  • CA Search (Chemical Abstracts)


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