DESIGN, SYNTHESIS, ANTIVIRAL, AND CYTOTOXIC EVALUATION OF NOVEL PHOSPHONYLATED 1,2,3-TRIAZOLES AS ACYCLIC NUCLEOTIDE ANALOGUES

被引：21

作者：

Glowacka, Iwona E. ^{[1
]}

Balzarini, Jan ^{[2
]}

Wroblewski, Andrzej E. ^{[1
]}

机构：

[1] Med Univ Lodz, Fac Pharm, Bioorgan Chem Lab, PL-90151 Lodz, Poland

[2] Katholieke Univ Leuven, Rega Inst Med Res, Louvain, Belgium

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2012年 / 31卷 / 04期

关键词：

Phosphonylated nucleosides; azidophosphonates; 1,3-dipolar cycloaddition 1,4-disubstituted-1,2,3-triazoles; phosphonic acid; CLICK-CHEMISTRY; BIOLOGICAL EVALUATION; INHIBITORS; DERIVATIVES; NUCLEOSIDES; BINDING; AZIDES; ACID; CYCLOADDITION; CIDOFOVIR;

D O I：

10.1080/15257770.2012.662611

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：

The 1,3-dipolar cycloaddition of diethyl 2-azidoethyl-, 3-azidopropyl-, 2-azido-1-hydroxyethyl-, 3-azido-2-hydroxypropylphosphonates with selected N-propargyl nucleobases gave a series of the phosphonylated 1,2,3-triazole acyclonucleosides in which the phosphonate residue and nucleobases were linked by three-and four-carbon chains. Under standard conditions (TMSBr, ethanol), all synthesized O,O-diethylphosphonates were transformed into the respective phosphonic acids. All compounds were evaluated in vitro for activity against a broad variety of DNA and RNA viruses. Unfortunately, no antiviral activity was observed at 100 mu M.

引用

页码：293 / 318

页数：26

共 63 条

[1]

Akri K.E., 2007, BIOORG MED CHEM LETT, V16, P6656

[2] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY [J].

ALVAREZ, R ;

VELAZQUEZ, S ;

SANFELIX, A ;

AQUARO, S ;

DECLERCQ, E ;

PERNO, CF ;

KARLSSON, A ;

BALZARINI, J ;

CAMARASA, MJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) :4185-4194

[3] Facile synthesis of phosphorylated azides in ionic liquids and their use in the preparation of 1,2,3-triazoles [J].

Artyushin, Oleg I. ;

Vorob'eva, Daria V. ;

Vasil'eva, Tamara P. ;

Osipov, Sergey N. ;

Roeschenthaler, Gerd-Volker ;

Odinets, Irina L. .

HETEROATOM CHEMISTRY, 2008, 19 (03) :293-300

[4] Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives [J].

Aufort, Marie ;

Herscovici, Jean ;

Bouhours, Pascale ;

Moreau, Nicole ;

Girard, Christian .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) :1195-1198

[5] Structural studies on bioactive compounds.: Part 36:: Design, synthesis and biological evaluation of pyrimethamine-based antifolates against Pneumocystis carinii [J].

Chan, DCM ;

Laughton, CA ;

Queener, SF ;

Stevens, MFG .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) :3001-3011

[6] Exploration of click reaction for the synthesis of modified nucleosides as chitin synthase inhibitors [J].

Chaudhary, Preeti M. ;

Chavan, Sayalee R. ;

Shirazi, Fazal ;

Razdan, Meenakshi ;

Nimkar, Prachi ;

Maybhate, Shailaja P. ;

Likhite, Anjali P. ;

Gonnade, Rajesh ;

Hazara, Braja G. ;

Deshpande, Mukund V. ;

Deshpande, Sunita R. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (06) :2433-2440

[7] Synthesis and biological activity of novel phosphonate derivatives containing of pyridyl and 1,2,3-triazole rings [J].

Chen, Xiao-Bao ;

Shi, De-Qing .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (05) :1134-1144

[8] A series of potent and selective, triazolylphenyl-based histone deacetylases inhibitors with activity against pancreatic cancer cells and Plasmodium falciparum [J].

Chen, Yufeng ;

Lopez-Sanchez, Miriam ;

Savoy, Doris N. ;

Billadeau, Daniel D. ;

Dow, Geoffrey S. ;

Kozikowski, Alan P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (12) :3437-3448

[9] Nucleosides and oligonucleotides containing 1,2,3-triazole residues with nucleobase tethers: Synthesis via the azide-alkyne 'click' reaction [J].

Chittepu, Padmaja ;

Sirivolu, Venkata Ramana ;

Seela, Frank .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (18) :8427-8439

[10]

Chu C.K., 2003, Antiviral Nucleosides: Chiral Synthesis and Chemotherapy

← 1 2 3 4 5 6 7 →