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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2002年 / 10卷 / 06期

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.

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页码：1813 / 1818

页数：6

相关论文

共 37 条

[11] Design and synthesis of monocyclic β-lactams as mechanism-based inhibitors of human cytomegalovirus protease. [J].

Borthwick, AD ;

Weingarten, G ;

Haley, TM ;

Tomaszewski, M ;

Wang, W ;

Hu, ZH ;

Bedard, J ;

Jin, HL ;

Yuen, L ;

Mansour, TS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (04) :365-370

[12] A novel and selective approach to enantiomerically pure bicyclic-trans-lactams via a titanium enolate of a thiopyridyl ester [J].

Cooke, JWB ;

Berry, MB ;

Caine, DM ;

Cardwell, KS ;

Cook, JS ;

Hodgson, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :334-336

[13] Small ring constrained peptidomimetics. Synthesis of epoxy peptidomimetics, inhibitors of cysteine proteases [J].

Demarcus, M ;

Ganadu, ML ;

Mura, GM ;

Porcheddu, A ;

Quaranta, L ;

Reginato, G ;

Taddei, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :697-706

[14]

DEZIEL R, 1996, BIOORG MED CHEM LETT, V6, P1437

[15] NEW BIOLOGICAL FUNCTIONS OF PROSTATE-SPECIFIC ANTIGEN [J].

DIAMANDIS, EP ;

YU, H .

JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM, 1995, 80 (05) :1515-1517

[16]

FIRESTONE RA, 1990, TETRAHEDRON, V46, P2255

[17] ASYMMETRIC-SYNTHESIS OF (1'R,3R,4R)-4-ACETOXY-3-(1'-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL)-2-AZETIDINONE AND OTHER 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM (S)-(+)-ETHYL 3-HYDROXYBUTANOATE - FORMAL TOTAL SYNTHESIS OF (+)-THIENAMYCIN [J].

GEORG, GI ;

KANT, J ;

GILL, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1129-1135

[18]

GRAUERT M, 1985, LIEBIGS ANN CHEM, P1817

[19] AZETIDIN-2-ONE DERIVATIVES AS INHIBITORS OF THROMBIN [J].

HAN, WT ;

TREHAN, AK ;

WRIGHT, JJK ;

FEDERICI, ME ;

SEILER, SM ;

MEANWELL, NA .

BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (08) :1123-1143

[20] Hydrolytic stability versus ring size in lactams: Implications for the development of lactam antibiotics and other serine protease inhibitors [J].

Imming, P ;

Klar, B ;

Dix, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (22) :4328-4331

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