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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 titleProject leaderProject codeProject type
Sinteza novih biološki aktivnih derivata nukleobaza i nukleotida[95066] Biserka Žinić098-0982914-2935MZOS
Mehanizam bioloških učinaka novih malih molekula na stanice tumora čovjeka[162671] Ljubica Glavaš Obrovac219-0982914-2176MZOS
Dizajn i sinteza bisamidina sa protutumorskim djelovanjem[1543] Miroslav Bajić053-0982914-2965MZOS
Depositing User: Biserka Žinić
Date Deposited: 11 Oct 2013 09:10
Last Modified: 06 Feb 2014 15:37
URI: http://fulir.irb.hr/id/eprint/769
DOI: 10.5562/cca2198

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