Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles

被引：4
作者：
Morsy, H. A. [1 ]
Mohammed, S. M. [2 ]
Hamid, A. M. Abdel [2 ]
Moustafa, A. H. [2 ]
El-Sayed, H. A. [2 ]
机构：
[1] Higher Inst Engn & Modern Technol, Cairo 13774, Egypt
[2] Zagazig Univ, Fac Sci, Dept Chem, Zagazig 44519, Egypt
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 56卷 / 01期
关键词：
2-oxonicotinonitrile; 1; 2; 3-triazole; nucleosides; click reaction; antimicrobial activity; SULFA-DRUGS; DESIGN; DERIVATIVES;
D O I：
10.1134/S1070428020010224
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile synthesis of a new series of 1,2,3-triazolyl nucleosides via one-pot click reaction is described. Acetylenic nicotinonitriles synthesized previously by alkylation of 4,6-diaryl-2-oxonicotinonitriles with propargyl bromide were involved in cycloaddition with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl azide in the presence of copper(I) to afford 1,2,3-triazole derivatives which were deprotected by treatment with aqueous triethylamine. The obtained 1,2,3-triazole nucleosides showed significant antimicrobial activities against some Gram-positive and Gram-negative bacteria and fungi.
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页码：143 / 147
页数：5
相关论文
共 18 条
[1]  
Adeniyi B A, 1996, Afr J Med Med Sci, V25, P221
[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]  
BAUER AW, 1966, AM J CLIN PATHOL, V45, P493
[4]   Synthesis of glucosylated 1,2,3-triazole derivatives [J].
Chen, XM ;
Li, ZJ ;
Ren, ZX ;
Huang, ZT .
CARBOHYDRATE RESEARCH, 1999, 315 (3-4) :262-267
[5]   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
[6]   Strategies in the design of antiviral drugs [J].
De Clercq, E .
NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (01) :13-25
[7]   In search of a selective antiviral chemotherapy [J].
DeClercq, E .
CLINICAL MICROBIOLOGY REVIEWS, 1997, 10 (04) :674-+
[8]   Pyrazole and Nicotinonitrile Derivatives Synthesized from Sulfa Drugs, and Their Antibacterial Activity [J].
El-Sayed, H. A. ;
Moustafa, A. H. ;
Fadda, A. A. ;
Abd El-Rahman, K. E. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (02) :339-347
[9]   A Series of Pyridines and Pyridine Based Sulfa-Drugs as Antimicrobial Agents: Design, Synthesis and Antimicrobial Activity [J].
El-Sayed, H. A. ;
Moustafa, A. H. ;
El-Torky, A. E. ;
Abd El-Salam, E. A. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (10) :2401-2408
[10]   Design, synthesis, and antimicrobial activity of fluorophore 1,2,3-triazoles linked nicotinonitrile derivatives [J].
El-Sayed, Hassan A. ;
Hamid, Atef M. Abdel ;
Mohammed, Samar M. ;
Moustafa, Ahmed H. .
SYNTHETIC COMMUNICATIONS, 2019, 49 (16) :2096-2105
12