Synthesis of New 1,2,3-Triazol-4-yl-quinazoline Nucleoside and Acyclonucleoside Analogues

被引:30
作者
Ouahrouch, Abdelaaziz [1 ,2 ]
Taourirte, Moha [1 ]
Engels, Joachim W. [3 ]
Benjelloun, Soumaya [4 ]
Lazrek, Hassan B. [2 ]
机构
[1] FSTG, Lab Bioorgan & Macromol Chem, Dept Chem, Marrakech 40000, Morocco
[2] Fac Sci Semlalia, Dept Chem, Lab Biomol & Med Chem, Marrakech 40000, Morocco
[3] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany
[4] Pasteur Inst Morocco, Viral Hepatitis Lab, Casablanca 20001, Morocco
关键词
quinazoline ribonucleosides; 1,2,3-triazole-acyclonucleosides; Huisgen cycloaddition; quinazolinone alkylation; HCV; ALKYNE 1,3-DIPOLAR CYCLOADDITION; ASSISTED CLICK CHEMISTRY; HEPATITIS-C; QUINAZOLINE DERIVATIVES; TRIAZOLYL-NUCLEOSIDES; BIOLOGICAL EVALUATION; TERMINAL ALKYNES; O-ALKYLATION; IN-VITRO; INTERFERON;
D O I
10.3390/molecules19033638
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
In this study, we describe the synthesis of 1,4-disustituted-1,2,3-triazolo-quinazoline ribonucleosides or acyclonucleosides by means of 1,3-dipolar cycloaddition between various O or N-alkylated propargyl-quinazoline and 1'-azido-2',3',5'-tri-O-benzoylribose or activated alkylating agents under microwave conditions. None of the compounds selected showed significant anti-HCV activity in vitro.
引用
收藏
页码:3638 / 3653
页数:16
相关论文
共 49 条
[1]   Microwave-assisted Niementowski reaction. Back to the roots [J].
Alexandre, FR ;
Berecibar, A ;
Besson, T .
TETRAHEDRON LETTERS, 2002, 43 (21) :3911-3913
[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]  
BOGENTOFT C, 1969, ACTA PHARM SUEC, V6, P489
[4]   Study of copper(I) catalysts for the synthesis of carbanucleosides via azide-alkyne 1,3-dipolar cycloaddition [J].
Broggi, Julie ;
Diez-Gonzalez, Silvia ;
Petersen, Jeffrey L. ;
Berteina-Raboin, Sabine ;
Nolan, Steven P. ;
Agrofoglio, Luigi A. .
SYNTHESIS-STUTTGART, 2008, (01) :141-148
[5]   Alkyne-azide click chemistry mediated carbanucleosides synthesis [J].
Broggi, Julie ;
Joubert, Nicolas ;
Aucagne, Vincent ;
Berteina-Raboin, Sabine ;
Diez-Gonzalez, S. ;
Nolan, Steve ;
Topalis, Dimitri ;
Deville-Bonne, Dominique ;
Balzarini, Jan ;
Neyts, Johan ;
Andrei, Graciela ;
Snoeck, Robert ;
Agrofoglio, Luigi A. .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12) :1391-1394
[6]   Click Azide-Alkyne Cycloaddition for the Synthesis of D-(-)-1,4-Disubstituted Triazolo-Carbanucleosides [J].
Broggi, Julie ;
Kumamoto, Hiroki ;
Berteina-Raboin, Sabine ;
Nolan, Steven P. ;
Agrofoglio, Luigi A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) :1880-1888
[7]   Synthesis of (±)-1,2,3-triazolo-3′-deoxy-4′-hydroxymethyl carbanucleosides via 'click' cycloaddition [J].
Broggi, Julie ;
Joubert, Nicolas ;
Diez-Gonzalez, Silvia ;
Berteina-Raboin, Sabine ;
Zevaco, Thomas ;
Nolan, Steven P. ;
Agrofoglio, Luigi A. .
TETRAHEDRON, 2009, 65 (06) :1162-1170
[8]   Boceprevir and Telaprevir in the Management of Hepatitis C Virus-Infected Patients [J].
Butt, Adeel A. ;
Kanwal, Fasiha .
CLINICAL INFECTIOUS DISEASES, 2012, 54 (01) :96-104
[9]   Synthesis of 1,3-diamino-7,8,9,10-tetrahydropyrido[3,2-f]-quinazolines. Inhibitors of Candida albicans dihydrofolate reductase as potential antifungal agents [J].
Chan, JH ;
Hong, JS ;
Kuyper, LF ;
Jones, ML ;
Baccanari, DP ;
Tansik, RL ;
Boytos, CM ;
Rudolph, SK ;
Brown, AD .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (01) :145-151
[10]   Click chemistry: Studies on the synthesis of novel fluorous tagged triazol-4-yl substituted quinazoline derivatives and their biological evaluation - Theoretical and experimental validation [J].
Chandrika, P. Mani ;
Yakaiah, T. ;
Gayatri, G. ;
Kumar, K. Pranay ;
Narsaiah, B. ;
Murthy, U. S. N. ;
Rao, A. Raghu Ram .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :78-84