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Pregled bibliografske jedinice broj: 304532

Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives


Gazivoda, Tatjana; Šokčević, Mario; Kralj, Marijeta; Šuman, Lidija; Pavelić, Krešimir; De Clercq, Erik; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Mintas, Mladen; Raić-Malić, Silvana
Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives // Journal of medicinal chemistry, 50 (2007), 17; 4105-4112 doi:10.1021/jm070324z (međunarodna recenzija, članak, znanstveni)


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Naslov
Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives

Autori
Gazivoda, Tatjana ; Šokčević, Mario ; Kralj, Marijeta ; Šuman, Lidija ; Pavelić, Krešimir ; De Clercq, Erik ; Andrei, Graciela ; Snoeck, Robert ; Balzarini, Jan ; Mintas, Mladen ; Raić-Malić, Silvana

Izvornik
Journal of medicinal chemistry (0022-2623) 50 (2007), 17; 4105-4112

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

Ključne riječi
C-5 alkynylated pyrimidines ; C-6 alkylfuro[2, 3-d]pyrimidines ; L-ascorbic acid ; antiviral and cytostatic activity evaluations

Sažetak
The novel C-5 alkynyl substituted pyrimidine (1-11) and furo[2, 3-d]pyrimidine derivatives (12-22) of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4', 5'-didehydro-5', 6'-dideoxy-L-ascorbic acid with terminal alkynes by using Sonogashira cross-coupling reaction conditions. The new compounds were evaluated for their cytostatic and antiviral activities. Among all evaluated compounds, the octynyl-substituted uracil derivative of L-ascorbic acid (3) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50 = 2-12 uM). Pyrimidine derivatives of L-ascorbic acid containing p-substituted phenylacetylene groups (8-11) displayed also a rather pronounced (IC50 = 3-37 uM) inhibitory effect toward all tumor cell lines. From the bicyclic series of compounds, 6-butylfuro[2, 3-d]pyrimidine derivative (12) and 6-p-bromophenylfuro[2, 3-d]pyrimidine derivative (19) showed the highest cytostatic activity (IC50 = 4.5-20 uM), particularly against malignant leukemia (L1210) and T-lymphocyte (Molt4/C8 and CEM) cells. Compounds 3 and 9 showed specific albeit moderate activity against cytomegalovirus (CMV, Davis strain, EC50 = 1.8 and 3.8 uM, respectively, for compounds 3 and 9) at a approximately 5-fold lower concentration than that required to show cytotoxicity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekti:
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)
MZOS-335-0982464-2393 - Molekularna obilježja miofibroblasta Dupuytrenove bolesti (Pavelić, Krešimir, MZOS ) ( POIROT)

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

Poveznice na cjeloviti tekst rada:

doi pubs.acs.org doi.org

Citiraj ovu publikaciju:

Gazivoda, Tatjana; Šokčević, Mario; Kralj, Marijeta; Šuman, Lidija; Pavelić, Krešimir; De Clercq, Erik; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Mintas, Mladen; Raić-Malić, Silvana
Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives // Journal of medicinal chemistry, 50 (2007), 17; 4105-4112 doi:10.1021/jm070324z (međunarodna recenzija, članak, znanstveni)
Gazivoda, T., Šokčević, M., Kralj, M., Šuman, L., Pavelić, K., De Clercq, E., Andrei, G., Snoeck, R., Balzarini, J., Mintas, M. & Raić-Malić, S. (2007) Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives. Journal of medicinal chemistry, 50 (17), 4105-4112 doi:10.1021/jm070324z.
@article{article, author = {Gazivoda, Tatjana and \v{S}ok\v{c}evi\'{c}, Mario and Kralj, Marijeta and \v{S}uman, Lidija and Paveli\'{c}, Kre\v{s}imir and De Clercq, Erik and Andrei, Graciela and Snoeck, Robert and Balzarini, Jan and Mintas, Mladen and Rai\'{c}-Mali\'{c}, Silvana}, year = {2007}, pages = {4105-4112}, DOI = {10.1021/jm070324z}, keywords = {C-5 alkynylated pyrimidines, C-6 alkylfuro[2, 3-d]pyrimidines, L-ascorbic acid, antiviral and cytostatic activity evaluations}, journal = {Journal of medicinal chemistry}, doi = {10.1021/jm070324z}, volume = {50}, number = {17}, issn = {0022-2623}, title = {Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives}, keyword = {C-5 alkynylated pyrimidines, C-6 alkylfuro[2, 3-d]pyrimidines, L-ascorbic acid, antiviral and cytostatic activity evaluations} }
@article{article, author = {Gazivoda, Tatjana and \v{S}ok\v{c}evi\'{c}, Mario and Kralj, Marijeta and \v{S}uman, Lidija and Paveli\'{c}, Kre\v{s}imir and De Clercq, Erik and Andrei, Graciela and Snoeck, Robert and Balzarini, Jan and Mintas, Mladen and Rai\'{c}-Mali\'{c}, Silvana}, year = {2007}, pages = {4105-4112}, DOI = {10.1021/jm070324z}, keywords = {C-5 alkynylated pyrimidines, C-6 alkylfuro[2, 3-d]pyrimidines, L-ascorbic acid, antiviral and cytostatic activity evaluations}, journal = {Journal of medicinal chemistry}, doi = {10.1021/jm070324z}, volume = {50}, number = {17}, issn = {0022-2623}, title = {Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4',5'-didehydro-L-ascorbic acid derivatives}, keyword = {C-5 alkynylated pyrimidines, C-6 alkylfuro[2, 3-d]pyrimidines, L-ascorbic acid, 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


Uključenost u ostale bibliografske baze podataka::


  • Chemical Abstracts
  • Excerpta Medica
  • Index Medicus


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