Solid-phase synthesis of α-hydroxy phosphonates and hydroxystatine amides.: Transition-state isosteres derived from resin-bound amino acid aldehydes

被引：25

作者：

Dolle, RE ^{[1
]}

Herpin, TF ^{[1
]}

Shimshock, YC ^{[1
]}

机构：

[1] Pharmacopeia Inc, Dept Chem, Princeton, NJ 08543 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(01)00097-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Resin-bound N-acylated amino acid aldehydes iv were converted in a single step to a-hydroxy phosphonates vii (Pudovik reaction) and in six-steps to hydroxystatine amides viii, demonstrating the utility of intermediates iv for constructing multiple aspartic acid transition-state isosteres. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1855 / 1858

页数：4

相关论文

共 14 条

[1] INHIBITORS OF ASPARTYL PROTEINASES [J].

ABDELMEGUID, SS .

MEDICINAL RESEARCH REVIEWS, 1993, 13 (06) :731-778

[2] Combinatorial method for the synthesis of alpha-hydroxy phosphonates on Wang resin [J].

Cao, XD ;

Mjalli, AMM .

TETRAHEDRON LETTERS, 1996, 37 (34) :6073-6076

[3] Identification of potent inhibitors of Plasmodium falciparum plasmepsin II from an encoded statine combinatorial library [J].

Carroll, CD ;

Patel, H ;

Johnson, TO ;

Guo, T ;

Orlowski, M ;

He, ZM ;

Cavallaro, CL ;

Guo, J ;

Oksman, A ;

Gluzman, IY ;

Connelly, J ;

Chelsky, D ;

Goldberg, DE ;

Dolle, RE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (17) :2315-2320

[4] Evaluation of a structure-based statine cyclic diamino amide encoded combinatorial library against plasmepsin II and cathepsin D [J].

Carroll, CD ;

Johnson, TO ;

Tao, S ;

Lauri, G ;

Orlowski, M ;

Gluzman, IY ;

Goldberg, DE ;

Dolle, RE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (22) :3203-3206

[5] Allylindium and allylboronic acid pinacolate: Mild reagents for the allylation of resin-bound aldehydes. Application to the solid-phase synthesis of hydroxypropylamines [J].

Cavallaro, CL ;

Herpin, T ;

McGuinness, BF ;

Shimshock, YC ;

Dolle, RE .

TETRAHEDRON LETTERS, 1999, 40 (14) :2711-2714

[6] RENIN INHIBITORS [J].

GREENLEE, WJ .

MEDICINAL RESEARCH REVIEWS, 1990, 10 (02) :173-236

[7] Potent, low-molecular-weight non-peptide inhibitors of malarial aspartyl protease plasmepsin II [J].

Haque, TS ;

Skillman, AG ;

Lee, CE ;

Habashita, H ;

Gluzman, IY ;

Ewing, TJA ;

Goldberg, DE ;

Kuntz, ID ;

Ellman, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) :1428-1440

[8] HIV PROTEASE - A NOVEL CHEMOTHERAPEUTIC TARGET FOR AIDS [J].

HUFF, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) :2305-2314

[9] Versatile approach to encoding combinatorial organic syntheses using chemically robust secondary amine tags [J].

Ni, ZJ ;

Maclean, D ;

Holmes, CP ;

Murphy, MM ;

Ruhland, B ;

Jacobs, JW ;

Gordon, EM ;

Gallop, MA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (08) :1601-1608

[10] THE RAPID IDENTIFICATION OF HIV PROTEASE INHIBITORS THROUGH THE SYNTHESIS AND SCREENING OF DEFINED PEPTIDE MIXTURES [J].

OWENS, RA ;

GESELLCHEN, PD ;

HOUCHINS, BJ ;

DIMARCHI, RD .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1991, 181 (01) :402-408