An alternative synthesis of peptidyl α-keto-2-oxazolines

被引:8
作者
Dunn, D [1 ]
Chatterjee, S [1 ]
机构
[1] Cephalon Inc, Dept Chem, W Chester, PA 19380 USA
关键词
D O I
10.1016/S0960-894X(98)00203-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Application of Wipf's protocol to generate alpha-keto-2-oxazolines is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1273 / 1276
页数:4
相关论文
共 15 条
[1]   Peptidyl alpha-keto thiazole as potent thrombin inhibitors [J].
Akiyama, Y ;
Tsutsumi, S ;
Hatsushiba, E ;
Ohuchi, S ;
Okonogi, T .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (05) :533-538
[2]  
BURKHART JP, 1988, TETRAHEDRON LETT, V29, P3343
[3]   Potent thrombin inhibitors that probe the S-1' subsite: Tripeptide transition state analogues based on a heterocycle-activated carbonyl group [J].
Costanzo, MJ ;
Maryanoff, BE ;
Hecker, LR ;
Schott, MR ;
Yabut, SC ;
Zhang, HC ;
AndradeGordon, P ;
Kauffman, JA ;
Lewis, JM ;
Krishnan, R ;
Tulinsky, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (16) :3039-3043
[4]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[5]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[6]   PEPTIDYL ALPHA-KETOHETEROCYCLIC INHIBITORS OF HUMAN NEUTROPHIL ELASTASE .3. IN-VITRO AND IN-VIVO POTENCY OF A SERIES OF PEPTIDYL ALPHA-KETOBENZOXAZOLES [J].
EDWARDS, PD ;
ZOTTOLA, MA ;
DAVIS, M ;
WILLIAMS, J ;
TUTHILL, PA .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (20) :3972-3982
[7]   PEPTIDYL ALPHA-KETOHETEROCYCLIC INHIBITORS OF HUMAN NEUTROPHIL ELASTASE .2. EFFECT OF VARYING THE HETEROCYCLIC RING ON IN-VITRO POTENCY [J].
EDWARDS, PD ;
WOLANIN, DJ ;
ANDISIK, DW ;
DAVIS, MW .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) :76-85
[8]   DESIGN, SYNTHESIS, AND KINETIC EVALUATION OF A UNIQUE CLASS OF ELASTASE INHIBITORS, THE PEPTIDYL ALPHA-KETOBENZOXAZOLES, AND THE X-RAY CRYSTAL-STRUCTURE OF THE COVALENT COMPLEX BETWEEN PORCINE PANCREATIC ELASTASE AND AC-ALA-PRO-VAL-2-BENZOXAZOLE [J].
EDWARDS, PD ;
MEYER, EF ;
VIJAYALAKSHMI, J ;
TUTHILL, PA ;
ANDISIK, DA ;
GOMES, B ;
STRIMPLER, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1854-1863
[9]   STEREOSPECIFIC SYNTHESIS OF PEPTIDYL ALPHA-KETO AMIDES AS INHIBITORS OF CALPAIN [J].
HARBESON, SL ;
ABELLEIRA, SM ;
AKIYAMA, A ;
BARRETT, R ;
CARROLL, RM ;
STRAUB, JA ;
TKACZ, JN ;
WU, CC ;
MUSSO, GF .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (18) :2918-2929
[10]   ASYMMETRIC ADDITION OF ORGANOMETALLICS TO CHIRAL KETOOXAZOLINES - PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXY ACIDS [J].
MEYERS, AI ;
SLADE, J .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (14) :2785-2791