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

Ismaili, Hamit; Ban, Željka; Matić, Josipa; Saftić, Dijana; Jukić, Marijana; Glavaš-Obrovac, Ljubica; Žinić, Biserka (2019) An Efficient Synthesis and In vitro Cytostatic Activity of 5-Aminosulfonyl Uracil Derivatives. Croatica Chemica Acta, 92 (2). pp. 269-277. ISSN 0011-1643

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Official URL: https://hrcak.srce.hr/227023

Abstract

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.

Item Type:

Article

Uncontrolled Keywords:

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

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects:

Project title	Project leader	Project code	Project type
UNSPECIFIED	UNSPECIFIED	VIF2017-MEFOS-8	UNSPECIFIED
Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka-	Ljubica Glavaš Obrovac	219-0982914-2176	MZOS
Višenamjensko očitavanje DNA / RNA sekundarne strukture molekularnim kemijskim senzorima-DNA/RNA-MolSense	Ivo Piantanida	IP-2013-11-1477	HRZZ
Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida-	Biserka Žinić	098-0982914-2935	MZOS