Exploring the potential of the β-thiolactones in bioorganic chemistry

被引:16
作者
Aubry, Sylvain [1 ]
Sasaki, Kaname [1 ]
Eloy, Laure [1 ]
Aubert, Genevieve [1 ]
Retailleau, Pascal [1 ]
Cresteil, Thierry [1 ]
Crich, David [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91190 Gif Sur Yvette, France
关键词
CYSTEINE PROTEINASE-INHIBITORS; FREE-RADICAL CHEMISTRY; PROTEASOME INHIBITORS; SALINOSPORAMIDE-A; MOLECULAR-STRUCTURE; COUPLING REACTIONS; CANCER-THERAPY; ACTIVE-SITE; CATHEPSIN-B; LACTONES;
D O I
10.1039/c1ob05967j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel peptide-based beta-thiolactones were synthesized and assayed for cytotoxicity against several human cancer cell lines, where they showed greater activity than the corresponding beta-lactones and beta-lactams. Several of the beta-thiolactones prepared showed strong inhibitory activity in vitro against human cathepsins B and L.
引用
收藏
页码:7134 / 7143
页数:10
相关论文
共 99 条
[51]  
MATHIAS LJ, 1979, SYNTHESIS-STUTTGART, P561
[52]  
MATIJASIC I, 1987, CROAT CHEM ACTA, V60, P285
[53]  
Matijasic I., 1984, CROAT CHEM ACTA, V54, P621
[54]  
MILINOVIC I, 1973, CROAT CHEM ACTA, V45, P551
[55]   Highly diastereoselective, tandem, three-component synthesis of tetrahydrofurans from ketoaldehydes via silylated β-lactone intermediates [J].
Mitchell, T. Andrew ;
Zhao, Cunxiang ;
Romo, Daniel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) :5026-5029
[56]   Double Diastereoselective, Nucleophile-Catalyzed Aldol Lactonizations (NCAL) Leading to β-Lactone Fused Carbocycles and Extensions to β-Lactone Fused Tetrahydrofurans [J].
Morris, Kay A. ;
Arendt, Kevin M. ;
Oh, Seong Ho ;
Romo, Daniel .
ORGANIC LETTERS, 2010, 12 (17) :3764-3767
[57]   Bioinspired Total Synthesis and Human Proteasome Inhibitory Activity of (-)-Salinosporamide A, (-)-Homosalinosporamide A, and Derivatives Obtained via Organonucleophile Promoted Bis-cyclizations [J].
Nguyen, Henry ;
Ma, Gil ;
Gladysheva, Tatiana ;
Fremgen, Trisha ;
Romo, Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :2-12
[58]   BOND ANGLES IN LACTONES AND LACTAMS [J].
NORSKOVLAURITSEN, L ;
BURGI, HB ;
HOFMANN, P ;
SCHMIDT, HR .
HELVETICA CHIMICA ACTA, 1985, 68 (01) :76-82
[59]   Proteasome inhibitors in cancer therapy: Lessons from the first decade [J].
Orlowski, Robert Z. ;
Kuhn, Deborah J. .
CLINICAL CANCER RESEARCH, 2008, 14 (06) :1649-1657
[60]  
POMMIER A, 1995, SYNTHESIS-STUTTGART, P729