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Original scientific paper

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

Fulltext: english, pdf (135 KB) pages 261-267 downloads: 670* cite
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. Retrieved from 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, no. 2, 2005, pp. 261-267. https://hrcak.srce.hr/20. Accessed 15 Sep. 2019.
Chicago 17th Edition
Kašnar-Šamprec, Jelena, Ljubica Glavaš-Obrovac, Marina Pavlak, Ivica Mihaljević, Vladimir Mrljak, Nikola Štambuk, Paško Konjevoda and Biserka Žinić. "Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives." Croatica Chemica Acta 78, no. 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), pp. 261-267. Available at: https://hrcak.srce.hr/20 (Accessed 15 September 2019)
Vancouver
Kašnar-Šamprec J, Glavaš-Obrovac Lj, Pavlak M, Mihaljević I, Mrljak V, Štambuk N, et al. Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives. Croatica Chemica Acta [Internet]. 2005 [cited 2019 September 15];78(2):261-267. Available from: 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, no. 2, pp. 261-267, 2005. [Online]. Available: https://hrcak.srce.hr/20. [Accessed: 15 September 2019]

Abstracts
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.

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

Hrčak ID: 20

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

[croatian]

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