Copper-catalyzed Synthesis and Antimicrobial Activity of Disubstituted 1,2,3-Triazoles Starting from 1-Propargyluracils and Ethyl (4-Azido-1,2,3-trihydroxybutyl)furan-3-carboxylate

被引：15
作者：
El-Sayed, Wael A. [2 ]
Abdel-Rahman, Adel A. -H. [1 ]
机构：
[1] Menoufia Univ, Fac Sci, Dept Chem, Shibin Al Kawm, Egypt
[2] Natl Res Ctr, Photochem Dept, Cairo, Egypt
来源：
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2010年 / 65卷 / 01期
关键词：
1,3-Dipolar Cycloaddition; 1,2,3-Triazoles; 1,3,4-Oxadiazoles; Antimicrobial Activity; AZIDE-ALKYNE CYCLOADDITION; C-FURYL GLYCOSIDES; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; SOLID-PHASE; ANTIBACTERIAL ACTIVITY; ANTI-HIV-1; ACTIVITY; TERMINAL ALKYNES; SIDE-CHAIN; DERIVATIVES;
D O I：
10.1515/znb-2010-0110
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition reactions of 1-propargyluracils 2a-h with the azido derivative 3 afforded the corresponding 1,2,3-triazoles 4a-h. Hydrazinolysis of the esters 4a-h gave the corresponding acid hydrazides 5a-h. Reaction of 5a-h with carbon disulfide in ethanol afforded 6a-h. The antimicrobial activity of compounds 4-6 was determined.
引用
收藏
页码：57 / 66
页数：10
相关论文
共 52 条
[1]   Amino acid derivatives, VIII:: synthesis and antimicrobial evaluation of α-amino acid esters bearing an indole side chain [J].
Abdel-Rahman, Adel A. -H. ;
El-Sayed, Wael A. ;
Abdel-Bary, Hamed M. ;
Abdel-Megied, Ahmed E. -S. ;
Morcy, Emad M. I. .
MONATSHEFTE FUR CHEMIE, 2008, 139 (09) :1095-1101
[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]  
Ates O, 1997, ARZNEIMITTEL-FORSCH, V47, P1134
[4]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[5]   Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors [J].
Brik, A ;
Muldoon, J ;
Lin, YC ;
Elder, JH ;
Goodsell, DS ;
Olson, AJ ;
Fokin, VV ;
Sharpless, KB ;
Wong, CH .
CHEMBIOCHEM, 2003, 4 (11) :1246-1248
[6]   Directed DNA metallization [J].
Burley, GA ;
Gierlich, J ;
Mofid, MR ;
Nir, H ;
Tal, S ;
Eichen, Y ;
Carell, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1398-1399
[7]  
Dehne H., 1994, In Methoden der Organischen Chemie (Houben-Weyl), Schaumann, V8, P305
[8]   ALKYLATING NUCLEOSIDES .1. SYNTHESIS AND CYTOSTATIC ACTIVITY OF N-GLYCOSYL(HALOMETHYL)-1,2,3-TRIAZOLES - NEW TYPE OF ALKYLATING AGENT [J].
DELASHERAS, FG ;
ALONSO, R ;
ALONSO, G .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (05) :496-501
[9]  
Dowsett M, 2001, CANCER RES, V61, P8452
[10]   Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(I-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones [J].
El-Emam, AA ;
Al-Deeb, OA ;
Al-Omar, M ;
Lehmann, J .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (19) :5107-5113
123456