The new unsaturated acyclic C-5 pyrimidine nucleoside analogues: Synthesis, cytostatic and anti-HIV evaluations

被引:0
作者
Gazivoda, Tatjana [1 ]
Raic-Malic, Silvana [1 ]
Kraljevic-Pavelic, Sandra
Pavelic, Kresimir
Balzarini, Jan
Mintas, Mladen [1 ]
机构
[1] Univ Zagreb, Fac Chem Engn & Technol, Dept Organ Chem, Zagreb 10000, Croatia
来源
CHEMISTRY OF NUCLEIC ACID COMPONENTS | 2008年 / 10卷
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中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of the novel C-5 alkynyl pyrimidine nucleoside analogues (1-14) in which the sugar moiety was replaced by the conformationally restricted (Z)- and (E)-2-butenyl spacer between the phthalimido and pyrimidine ring were synthesized by using Sonogashira cross-coupling reaction. Cytostatic activity evaluation of the novel compounds showed that E-isomers (8-14) exhibited better cytostatic activities than the corresponding Z-isomers (1-7). The compounds 3, 4 and 14 expressed some marginal inhibitory activity against HIV-1 and HIV-2.
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页码:439 / 441
页数:3
相关论文
共 9 条
[1]   SYNTHESIS AND ANTITUMOR AND ANTIVIRAL PROPERTIES OF 5-ALKYL-2'-DEOXYURIDINES, 3',5'-CYCLIC MONOPHOSPHATES, AND NEUTRAL CYCLIC TRIESTERS [J].
BERES, J ;
BENTRUDE, WG ;
BALZARINI, J ;
DECLERCQ, E ;
OTVOS, L .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (04) :494-499
[3]   The novel pyrimidine and purine derivatives of L-ascorbic acid:: synthesis, one- and two-dimensional 1H and 13C NMR study, cytostatic and antiviral evaluation [J].
Gazivoda, T ;
Plevnik, M ;
Plavec, J ;
Kraljevic, S ;
Kralj, M ;
Pavelic, K ;
Balzarini, J ;
De Clercq, E ;
Mintas, M ;
Raci-Malic, S .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) :131-139
[4]   Synthesis and antiviral and cytostatic evaluations of the new C-5 substituted pyrimidine and furo[2,3-d] pyrimidine 4′,5′-didehydro-L-ascorbic acid derivatives [J].
Gazivoda, Tatjana ;
Sokcevic, Mario ;
Kralj, Marijeta ;
Suman, Lidija ;
Pavelic, Kresimir ;
De Clercq, Erik ;
Andrei, Graciela ;
Snoeck, Robert ;
Balzarini, Jan ;
Mintas, Mladen ;
Raic-Malic, Silvana .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (17) :4105-4112
[5]   The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of L-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations [J].
Gazivoda, Tatjana ;
Raic-Malic, Silvana ;
Marjanovic, Marko ;
Kralj, Marijeta ;
Pavelic, Kresimir ;
Balzarini, Jan ;
De Clercq, Erik ;
Mintas, Mladen .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (02) :749-758
[6]   5-SUBSTITUTED-2'-DEOXYURIDINES AS ANTI-HSV-1 AGENTS - SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP [J].
HERDEWIJN, PAMM .
ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1994, 5 (03) :131-146
[7]   Synthesis, X-ray crystal structural study, antiviral and cytostatic evaluations of the novel unsaturated acyclic and epoxide nucleoside analogues [J].
Kristafor, Vedran ;
Raic-Malic, Silvana ;
Cetina, Mario ;
Kralj, Marijeta ;
Suman, Lidija ;
Pavelic, Kresimir ;
Balzarini, Jan ;
De Clereq, Erik ;
Mintas, Mladen .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (23) :8126-8138
[8]   Novel pyrimidine and purine derivatives of L-ascorbic acid: Synthesis and biological evaluation [J].
Raic-Malic, S ;
Hergold-Brundic, A ;
Nagl, A ;
Grdisa, M ;
Pavelic, K ;
De Clercq, E ;
Mintas, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (14) :2673-2678
[9]   Synthesis and antitumor activities of novel pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid and 4,5-didehydro-5,6-dideoxy-L-ascorbic acid [J].
Raic-Malic, S ;
Svedruzic, D ;
Gazivoda, T ;
Marunovic, A ;
Hergold-Brundic, A ;
Nagl, A ;
Balzarini, J ;
De Clercq, E ;
Mintas, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (25) :4806-4811