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https://doi.org/10.5562/cca3273

Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues

Luka Krstulović ; Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000 Zagreb, Croatia
Dijana Saftić ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Hamit Ismaili ; Faculty of Mathematics and Natural Sciences, University of Pristina, Agim Ramadani n.n. 10000, Pristina, Kosovo
Miroslav Bajić ; Faculty of Veterinary Medicine, University of Zagreb, Heinzelova 55, HR-10000 Zagreb, Croatia
Ljubica Glavaš-Obrovac   ORCID icon orcid.org/0000-0001-7497-296X ; Department of Medicinal Chemistry, Biochemistry and Laboratory Medicine, Faculty of Medicine, Josip Juraj Strossmayer University of Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Biserka Žinić   ORCID icon orcid.org/0000-0002-1536-7142 ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia

Puni tekst: engleski, pdf (2 MB) str. 625-636 preuzimanja: 433* citiraj
APA 6th Edition
Krstulović, L., Saftić, D., Ismaili, H., Bajić, M., Glavaš-Obrovac, Lj. i Žinić, B. (2017). Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues. Croatica Chemica Acta, 90 (4), 625-636. https://doi.org/10.5562/cca3273
MLA 8th Edition
Krstulović, Luka, et al. "Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues." Croatica Chemica Acta, vol. 90, br. 4, 2017, str. 625-636. https://doi.org/10.5562/cca3273. Citirano 01.12.2020.
Chicago 17th Edition
Krstulović, Luka, Dijana Saftić, Hamit Ismaili, Miroslav Bajić, Ljubica Glavaš-Obrovac i Biserka Žinić. "Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues." Croatica Chemica Acta 90, br. 4 (2017): 625-636. https://doi.org/10.5562/cca3273
Harvard
Krstulović, L., et al. (2017). 'Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues', Croatica Chemica Acta, 90(4), str. 625-636. https://doi.org/10.5562/cca3273
Vancouver
Krstulović L, Saftić D, Ismaili H, Bajić M, Glavaš-Obrovac Lj, Žinić B. Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues. Croatica Chemica Acta [Internet]. 2017 [pristupljeno 01.12.2020.];90(4):625-636. https://doi.org/10.5562/cca3273
IEEE
L. Krstulović, D. Saftić, H. Ismaili, M. Bajić, Lj. Glavaš-Obrovac i B. Žinić, "Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues", Croatica Chemica Acta, vol.90, br. 4, str. 625-636, 2017. [Online]. https://doi.org/10.5562/cca3273

Sažetak
Two novel series of N-sulfonylamidino pyrimidine derivatives were synthesized via Cu-catalyzed three-component reaction of propargylated nucleobases with different benzenesulfonyl azides and amines. In this way 4-acetamido, 4-methyl and 4-carboxybenzenesulfonyl amidine products 15-26 in the uracil series and 4-acetamidobenzenesulfonyl amidine derivatives 27-29 in the cytosine series were prepared in 34-69 % yields. Attempts to prepare N-sulfonylamidino cytosine derivatives in reaction with 4-methylbenzenesulfonyl azide were unsuccessful. The cytosine derivatives 32 and 33 were prepared from the N-sulfonylamidino uracil derivatives via the C4 triazole intermediates.
The prepared N-sulfonylamidino pyrimidine derivatives 1-28 were tested for the antiproliferative activity on a panel of seven tumor cell lines of different histological origin (HeLa, Caco-2, NCI-H358, Raji, HuT78, K562, Jurkat) and on normal MDCK I cells. Most of the synthesized compounds showed antiproliferative activity on the tested cell lines.

Creative Commons License This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi
pyrimidines; N-sulfonylamidines; multi-component synthesis; copper(I); in vitro

Hrčak ID: 198182

URI
https://hrcak.srce.hr/198182

Posjeta: 636 *