Efficient and highly stereoselective synthesis of a β-lactam inhibitor of the serine protease prostate-specific antigen

被引:34
作者
Annunziata, R
Benaglia, M
Cinquini, M
Cozzi, F
Puglisi, A
机构
[1] Univ Milan, Ctr CNR, I-20133 Milan, Italy
[2] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
关键词
D O I
10.1016/S0968-0896(02)00017-2
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An efficient synthesis of a beta-lactam precursor of the serine protease, prostate-specific antigen inhibitor 1 has been accomplished. The synthesis relies on two completely stercoselective reactions that allow the introduction of the stereocenters at C-3 and C-4 of the azetidinone ring in a predictable manner. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1813 / 1818
页数:6
相关论文
共 37 条
[1]  
Achilles K, 2000, PHARMAZIE, V55, P798
[2]   Design and synthesis of novel monocyclic beta-lactam inhibitors of prostate specific antigen [J].
Adlington, RM ;
Baldwin, JE ;
Chen, BN ;
Cooper, SL ;
McCoull, W ;
Pritchard, GJ ;
Howe, TJ ;
Becker, GW ;
Hermann, RB ;
McNulty, AM ;
Neubauer, BL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (13) :1689-1694
[3]   SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - INFLUENCE OF THE IMINE STRUCTURE ON THE TRANS/CIS STEREOSELECTIVITY [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
COZZI, F ;
PONZINI, F ;
RAIMONDI, L .
TETRAHEDRON, 1994, 50 (09) :2939-2948
[4]  
Annunziata R, 1999, EUR J ORG CHEM, V1999, P3067
[5]   STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
COZZI, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4155-4162
[6]   Stereoselective synthesis of 2-azetidinones as cholesterol-absorption inhibitors [J].
Annunziata, R ;
Benaglia, M ;
Cinquini, M ;
Cozzi, F .
TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4841-4849
[7]   PHOTOCHEMICAL TRANSFORMATIONS .19. SOME PHOTOSENSITIVE PROTECTING GROUPS [J].
BARTON, DHR ;
CHOW, YL ;
COX, A ;
KIRBY, GW .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JUN) :3571-&
[8]  
BEARDSELL M, 2001, J CHEM SOC CHEM COMM
[9]  
Benaglia M, 2000, EUR J ORG CHEM, V2000, P563
[10]   Inhibition of human cytomegalovirus protease by monocyclic β-lactam derivatives:: Kinetic characterization using a fluorescent probe [J].
Bonneau, PR ;
Hasani, F ;
Plouffe, C ;
Malenfant, E ;
LaPlante, SR ;
Guse, I ;
Ogilvie, WW ;
Plante, R ;
Davidson, WC ;
Hopkins, JL ;
Morelock, MM ;
Cordingley, MG ;
Déziel, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :2965-2973