Original scientific paper

https://doi.org/10.5562/cca3567

An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives

Hamit Ismaili ; Faculty of Mathematics and Natural Sciences, University of Pristina, Agim Ramadani n.n. 10000, Pristina, Kosovo
Željka Ban ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Josipa Matić ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 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
Marijana Jukić ; Department of Medicinal Chemistry, Biochemistry and Laboratory Medicine, Faculty of Medicine, Josip Juraj Strossmayer University of Osijek, Huttlerova 4, HR-31000 Osijek, Croatia
Ljubica Glavaš-Obrovac 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 ; Laboratory for Biomolecular Interactions and Spectroscopy, Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia

Abstract

Efficient synthesis of 5-aminosulfonyl uracil derivatives 2-9 and results of their antiproliferative activity are provided. Sulfonylation of the amino group in 5-aminouracil 1 with selected arylsulfonyl chlorides occurs regioselectively when the reaction is carried out in pyridine at room temperature. Simple isolation of the products by recrystallization of the crude product mixture from aqueous methanol provides good to excellent yields. The prepared 5-aminosulfonyl uracil derivatives 2-9 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, Jurkat, K562) and normal MDCK I cells. Derivatives 2-9 were found more efficient to lymphoma and leukemia cells compared to solid tumor and normal cells.

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

Keywords

5-aminouracil; arylsulfonyl chlorides; 5-aminosulfonyl uracil derivatives; in vitro; anticancer activity

Hrčak ID:

227023

URI

https://hrcak.srce.hr/227023

Publication date:

29.7.2019.

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