Formation of isoxazoles using cerium ammonium nitrate (CAN):: A one-pot synthesis of glycomimetics

被引:22
作者
Beha, Sara [1 ]
Giguere, Denis [1 ]
Patnam, Ramesh [1 ]
Roy, Rene [1 ]
机构
[1] Univ Quebec, Dept Chem, Montreal, PQ H3C 3P8, Canada
关键词
carbohydrates; cycloadditions; heterocycles; isoxazoles; CAN(IV);
D O I
10.1055/s-2006-947330
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3-Dipolar cycloaddition reactions of carbohydrate dipolarophiles with cerium(IV) ammonium nitrate CAN(IV) in acetone, acetophenone, or pinacolone yielded the corresponding 3,5-disubstituted isoxazoles, stable pharmacophores for glycomimetic syntheses.
引用
收藏
页码:1739 / 1743
页数:5
相关论文
共 68 条
[1]   Galectin-3 precipitates as a pentamer with synthetic multivalent carbohydrates and forms heterogeneous cross-linked complexes [J].
Ahmad, N ;
Gabius, HJ ;
André, S ;
Kaltner, H ;
Sabesan, S ;
Roy, R ;
Liu, BC ;
Macaluso, F ;
Brewer, CF .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (12) :10841-10847
[2]   First demonstration of differential inhibition of lectin binding by synthetic tri- and tetravalent glycoclusters from cross-coupling of rigidified 2-propynyl lactoside [J].
André, S ;
Liu, BC ;
Gabius, HJ ;
Roy, R .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (22) :3909-3916
[3]  
[Anonymous], 1988, NITRILE OXIDES NITRO
[4]   Synthesis and protein binding properties of T-antigen containing GlycoPAMAM dendrimers [J].
Baek, MG ;
Roy, R .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (01) :11-17
[5]   Baylis-Hillman reaction assisted parallel synthesis of 3,5-disubstituted isoxazoles and their in vivo bioevaluation as antithrombotic agents [J].
Batra, S ;
Roy, AK ;
Patra, A ;
Bhaduri, AP ;
Surin, WR ;
Raghavan, SAV ;
Sharma, P ;
Kapoor, K ;
Dikshit, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2059-2077
[6]   Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues [J].
Berecibar, A ;
Grandjean, C ;
Siriwardena, A .
CHEMICAL REVIEWS, 1999, 99 (03) :779-844
[7]  
Bode JW, 2001, ANGEW CHEM INT EDIT, V40, P2082, DOI 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO
[8]  
2-1
[9]   Receptor binding studies disclose a novel class of high-affinity inhibitors of the Escherichia coli FimH adhesin [J].
Bouckaert, J ;
Berglund, J ;
Schembri, M ;
De Genst, E ;
Cools, L ;
Wuhrer, M ;
Hung, CS ;
Pinkner, J ;
Slättegård, R ;
Zavialov, A ;
Choudhury, D ;
Langermann, S ;
Hultgren, SJ ;
Wyns, L ;
Klemm, P ;
Oscarson, S ;
Knight, SD ;
De Greve, H .
MOLECULAR MICROBIOLOGY, 2005, 55 (02) :441-455
[10]  
Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, V1, P291