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Croatica Chemica Acta, Vol.78 No.2 Lipanj 2005.

Izvorni znanstveni članak

Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives

Jelena Kašnar-Šamprec
Ljubica Glavaš-Obrovac
Marina Pavlak
Ivica Mihaljević
Vladimir Mrljak
Nikola Štambuk
Paško Konjevoda
Biserka Žinić

Puni tekst: engleski, pdf (135 KB) str. 261-267 preuzimanja: 619* citiraj
APA 6th Edition
Kašnar-Šamprec, J., Glavaš-Obrovac, Lj., Pavlak, M., Mihaljević, I., Mrljak, V., Štambuk, N., ... Žinić, B. (2005). Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives. Croatica Chemica Acta, 78 (2), 261-267. Preuzeto s https://hrcak.srce.hr/20
MLA 8th Edition
Kašnar-Šamprec, Jelena, et al. "Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives." Croatica Chemica Acta, vol. 78, br. 2, 2005, str. 261-267. https://hrcak.srce.hr/20. Citirano 23.07.2018.
Chicago 17th Edition
Kašnar-Šamprec, Jelena, Ljubica Glavaš-Obrovac, Marina Pavlak, Ivica Mihaljević, Vladimir Mrljak, Nikola Štambuk, Paško Konjevoda i Biserka Žinić. "Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives." Croatica Chemica Acta 78, br. 2 (2005): 261-267. https://hrcak.srce.hr/20
Harvard
Kašnar-Šamprec, J., et al. (2005). 'Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives', Croatica Chemica Acta, 78(2), str. 261-267. Preuzeto s: https://hrcak.srce.hr/20 (Datum pristupa: 23.07.2018.)
Vancouver
Kašnar-Šamprec J, Glavaš-Obrovac Lj, Pavlak M, Mihaljević I, Mrljak V, Štambuk N i sur. Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives. Croatica Chemica Acta [Internet]. 15.06.2005. [pristupljeno 23.07.2018.];78(2):261-267. Dostupno na: https://hrcak.srce.hr/20
IEEE
J. Kašnar-Šamprec, et al., "Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives", Croatica Chemica Acta, vol.78, br. 2, str. 261-267, Srpanj 2018. [Online]. Dostupno na: https://hrcak.srce.hr/20. [Citirano: 23.07.2018.]

Sažetak
Large scale preparation of N-1-sulfonylcytosine derivatives has been optimized. The best method was the condensation reaction of silylated cytosine (1) with p-toluenesulfonyl chloride in acetonitrile. Depending on the isolation procedure, 1-(p-toluenesulfonyl)cytosine 2 and 1-(p- -toluenesulfonyl)cytosine hydrochloride 3 were isolated in 80 % and 75 % yields, respectively. The NMR evidence presented shows that 2 appears as a common keto-amino tautomer in DMSO-d6 solution while its hydrochloride 3 forms exclusively the rare keto imino tautomer. N-1-Sulfonylcytosine derivatives 2 and 3 were investigated for possible cytotoxic activity on human normal fibroblasts (WI38), human pancreatic adenocarcinoma cells (MIAPaCa2), poorly differentiated cells from lymph node metastases of colon carcinoma (SW-620), and human Burkitt lymphoma cells (Raji). MTT-cytotoxicity screens in human tissue culture cell lines
showed that both investigated compounds demonstrated antiproliferative activity in different histological types of tumors. In comparison with 5-fluorouracil, some of N-1-sulfonylcytosine
derivatives showed 10 times stronger activity, with respect IC50. The inhibitory effect of the investigated derivatives on normal human cells was lower compared to their antitumor effects. In addition to antitumor effects, hematological findings following the parenteral administration of substances were also investigated.

Ključne riječi
N-1-sulfonylcytosine derivatives: in vitro antiproliferative effect; antitumor activity; hematological findings

Hrčak ID: 20

URI
https://hrcak.srce.hr/20

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