EFFICIENT ONE-POT SYNTHESIS OF POLYSUBSTITUTED 6-[(1H-1,2,3-TRIAZOL-1-YL)METHYL]URACILS THROUGH THE "CLICK" PROTOCOL

被引：11

作者：

Jansa, Petr ^{[1
]}

Spacek, Petr ^{[1
]}

Votruba, Ivan ^{[1
]}

Brehova, Petra ^{[1
]}

Dracinsky, Martin ^{[1
]}

Klepetarova, Blanka ^{[1
]}

Janeba, Zlatko ^{[1
]}

机构：

[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, VVI, CR-16610 Prague 6, Czech Republic

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2011年 / 76卷 / 09期

关键词：

Nucleosides; Nucleotides; Biological activity; Heterocycles; Phosphorus; Click chemistry; ACYCLIC NUCLEOSIDE PHOSPHONATES; 5-PHOSPHONO-PENT-2-EN-1-YL NUCLEOSIDES; INHIBITORS; ANALOGS; DERIVATIVES; NUCLEOTIDE; DISCOVERY;

D O I：

10.1135/cccc2011074

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The preparation of several triazolo acyclic nucleosides and triazolo acyclic nucleoside phosphonates is described. The synthetic methodology has been developed as an efficient one-pot Cu(I)-catalyzed azide alkyne Huisgen "click" cycloaddition. A novel Cu(I)-catalyzed decarboxylation reaction of 1-substituted 1H-1,2,3-triazole-4-carboxylic acids at room temperature was observed and used for the preparation of 1-substituted 1H-1,2,3-triazoles. As congeners of TPI (Taiho pharmaceutical inhibitor), the prepared compounds were screened as potential inhibitors of human thymidine phosphorylase, but no inhibitory activity was observed.

引用

页码：1121 / 1131

页数：11

共 37 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] Cu(I)-Catalyzed Huisgen Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction in Nucleoside, Nucleotide, and Oligonucleotide Chemistry [J].

Amblard, Franck ;

Cho, Jong Hyun ;

Schinazi, Raymond F. .

CHEMICAL REVIEWS, 2009, 109 (09) :4207-4220

[3] CRYSTALS version 12: software for guided crystal structure analysis [J].

Betteridge, PW ;

Carruthers, JR ;

Cooper, RI ;

Prout, K ;

Watkin, DJ .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2003, 36 :1487-1487

[4] The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination reactions of purines [J].

Cechova, Lucie ;

Jansa, Petr ;

Sala, Michal ;

Dracinsky, Martin ;

Holy, Antonin ;

Janeba, Zlatko .

TETRAHEDRON, 2011, 67 (05) :866-871

[5] Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: A new class of antiviral acyclic nucleoside phosphonates [J].

Choo, Hyunah ;

Beadle, James R. ;

Chong, Youhoon ;

Trahan, Julissa ;

Hostetler, Karl Y. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) :1771-1779

[6] Antiviral activities of novel 5-phosphono-pent-2-en-1-yl nucleosides and their alkoxyalkyl phosphonoesters [J].

Choo, Hyunah ;

Beadle, James R. ;

Kern, Earl R. ;

Prichard, Mark N. ;

Keith, Kathy A. ;

Hartline, Caroll B. ;

Trahan, Julissa ;

Aldern, Kathy A. ;

Korba, Brent E. ;

Hostetler, Karl Y. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2007, 51 (02) :611-615

[7] Acyclic nucleoside phosphonates: A key class of antiviral drugs [J].

De Clercq, E ;

Holy, A .

NATURE REVIEWS DRUG DISCOVERY, 2005, 4 (11) :928-940

[8] The Discovery of Antiviral Agents: Ten Different Compounds, Ten Different Stories [J].

De Clercq, Erik .

MEDICINAL RESEARCH REVIEWS, 2008, 28 (06) :929-953

[9] Three decades of antiviral drugs [J].

De Clercq, Erik .

NATURE REVIEWS DRUG DISCOVERY, 2007, 6 (12) :941-941

[10] Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition [J].

Diab, Sonia Amel ;

Hienzch, Antje ;

Lebargy, Cyril ;

Guillarme, Stephane ;

Pfund, Emmanuel ;

Lequeux, Thierry .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (21) :4481-4490

← 1 2 3 4 →