Liquid-phase combinatorial synthesis of alicyclic β-lactams via Ugi four-component reaction

被引:85
作者
Gedey, S
Van der Eycken, J
Fulöp, F
机构
[1] Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary
[2] State Univ Ghent, Dept Organ Chem, B-9000 Ghent, Belgium
关键词
D O I
10.1021/ol025986r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Alicyclic beta-lactams were successfully synthesized via a parallel liquid-phase Ugi four-center three-component reaction (U-4C-3CR), starting from alicyclic beta-amino acids such as cis-2-aminocyclohexanecarboxylic acid, cis-2-aminocyclopentanecarboxylic acid, 2,3-diexo-3-aminobicyclo[2.2.1]heptane-2-carboxylic acid and some of their partially unsaturated analogues. A six-membered mixture-based combinatorial library of beta-lactams was also generated.
引用
收藏
页码:1967 / 1969
页数:3
相关论文
共 45 条
[1]  
Achilles K, 2000, ARCH PHARM, V333, P243, DOI 10.1002/1521-4184(20008)333:8<243::AID-ARDP243>3.3.CO
[2]  
2-F
[3]   Synthesis and characterization of trans-2-aminocyclohexanecarboxylic acid oligomers:: An unnatural helical secondary structure and implications for β-peptide tertiary structure [J].
Appella, DH ;
Christianson, LA ;
Karle, IL ;
Powell, DR ;
Gellman, SH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6206-6212
[4]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[5]   STEREOCHEMICAL STUDIES .83. SATURATED HETEROCYCLES .76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES [J].
BERNATH, G ;
STAJER, G ;
SZABO, AE ;
FULOP, F ;
SOHAR, P .
TETRAHEDRON, 1985, 41 (07) :1353-1365
[6]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[7]  
2-A
[8]   Design, synthesis and stability of N-acyloxymethyl- and N-aminocarbonyloxymethyl-2-azetidinones as human leukocyte elastase inhibitors [J].
Clemente, A ;
Domingos, A ;
Grancho, AP ;
Iley, J ;
Moreira, R ;
Neres, J ;
Palma, N ;
Santana, AB ;
Valente, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (08) :1065-1068
[9]  
Dömling A, 1998, COMB CHEM HIGH T SCR, V1, P1
[10]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO