Synthesis of Novel Aliphatic N-sulfonylamidino Thymine Derivatives by Cu(I)-catalyzed Three-component Coupling Reaction

Krstulović, Luka; Ismaili, Hamit; Višnjevac, Aleksandar; Glavaš-Obrovac, Ljubica; Žinić, Biserka (2012) Synthesis of Novel Aliphatic N-sulfonylamidino Thymine Derivatives by Cu(I)-catalyzed Three-component Coupling Reaction. Croatica Chemica Acta, 85 (4). pp. 525-534. ISSN 0011-1643

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Abstract

A series of new aliphatic N-sulfonylamidino thymine derivatives containing nucleobase, N-sulfonyl and amidine pharmacophores in the structure were synthesized by Cu(I)-catalyzed three-component coupling of 1-propargyl thymine, benzenesulfonyl azides and amines or ammonium salts. Preliminary in vitro antitumor screening (human cervix adenocarcinoma -HeLa and leukemia cells - Jurkat) revealed promising activities of N,N-diethyl- (2) and N-4-cyanobenzyl- (6) derivatives of 4-acetamido-benzenesulfonyl amidine.

Item Type:	Article
Uncontrolled Keywords:	alkynes; azides; copper; nucleobases; N-sulfonylamidine; copper-catalyzed decomposition; carcinoma in-vivo; one-pot synthesis; click chemistry; sulfonylpyrimidine derivatives; benzenesulfonyl azide; diazotransfer reagent; antitumor-activity; crystal-structures; terminal alkynes
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry Division of Physical Chemistry
Projects:	Project title Project leader Project code Project type Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida [95066] Biserka Žinić 098-0982914-2935 MZOS Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka [162671] Ljubica Glavaš Obrovac 219-0982914-2176 MZOS Dizajn i sinteza bisamidina sa protutumorskim djelovanjem [1543] Miroslav Bajić 053-0982914-2965 MZOS
Depositing User:	Biserka Žinić
Date Deposited:	11 Oct 2013 09:10
URI:	http://fulir.irb.hr/id/eprint/769
DOI:	10.5562/cca2198

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