Novel cyclourethane-derived HIV protease inhibitors: A ring-closing olefin metathesis based strategy

被引：10

作者：

Ghosh, AK

Swanson, LM

Liu, CF

Hussain, KA

Cho, H

Walters, DE

Holland, L

Buthod, J

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

[2] Finch Univ Hlth Sci Chicago Med Sch, Dept Biol Chem, N Chicago, IL 60064 USA

[3] IIT, Res Inst, Dept Life Sci, Chicago, IL 60616 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 15期

关键词：

D O I：

10.1016/S0960-894X(02)00300-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel macrocyclic urethanes incorporating a (R)-hydroxyethylamine isostere was designed and synthesized. Ring size and substituent efffects have been investigated. Cyclourethanes containing 14- to 16-membered rings exhibited low nanomolar inhibitory potencies against HIV-1 protease. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1993 / 1996

页数：4

相关论文

共 18 条

[1] Recent developments in antiretroviral therapies [J].

Cihlar, T ;

Bischofberger, N .

ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 35, 2000, 35 :177-189

[2] ANTIVIRAL PROPERTIES OF RO 31-8959, AN INHIBITOR OF HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) PROTEINASE [J].

CRAIG, JC ;

DUNCAN, IB ;

HOCKLEY, D ;

GRIEF, C ;

ROBERTS, NA ;

MILLS, JS .

ANTIVIRAL RESEARCH, 1991, 16 (04) :295-305

[3] A distinct binding mode of a hydroxyethylamine isostere inhibitor of HIV-1 protease [J].

Dohnálek, J ;

Hasek, J ;

Dusková, J ;

Petroková, H ;

Hradilek, M ;

Soucek, M ;

Konvalinka, J ;

Brynda, J ;

Sedlácek, J ;

Fábry, M .

ACTA CRYSTALLOGRAPHICA SECTION D-BIOLOGICAL CRYSTALLOGRAPHY, 2001, 57 :472-476

[4] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[5] HIV-protease inhibitors [J].

Flexner, C .

NEW ENGLAND JOURNAL OF MEDICINE, 1998, 338 (18) :1281-1292

[6] Potent HIV protease inhibitors incorporating high-affinity P2-ligands and (R)-(hydroxyethylamino)sulfonamide isostere [J].

Ghosh, AK ;

Kincaid, JF ;

Cho, WH ;

Walters, DE ;

Krishnan, K ;

Hussain, KA ;

Koo, Y ;

Cho, H ;

Rudall, C ;

Holland, L ;

Buthod, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (06) :687-690

[7] N,N'-DISUCCINIMIDYL CARBONATE - A USEFUL REAGENT FOR ALKOXYCARBONYLATION OF AMINES [J].

GHOSH, AK ;

DUONG, TT ;

MCKEE, SP ;

THOMPSON, WJ .

TETRAHEDRON LETTERS, 1992, 33 (20) :2781-2784

[8] Structure-based design of non-peptide HIV protease inhibitors [J].

Ghosh, AK ;

Shin, D ;

Swanson, L ;

Krishnan, K ;

Cho, H ;

Hussain, KA ;

Walters, DE ;

Holland, L ;

Buthod, J .

FARMACO, 2001, 56 (1-2) :29-32

[9] Convenient synthesis of novel macrocyclic urethanes: Alkoxycarbonylation of amines and ring-closing metathesis strategy [J].

Ghosh, AK ;

Hussain, KA .

TETRAHEDRON LETTERS, 1998, 39 (14) :1881-1884

[10] POTENT HIV PROTEASE INHIBITORS - THE DEVELOPMENT OF TETRAHYDROFURANYLGLYCINES AS NOVEL P(2)-LIGANDS AND PYRAZINE AMIDES AS P(3)-LIGANDS [J].

GHOSH, AK ;

THOMPSON, WJ ;

HOLLOWAY, MK ;

MCKEE, SP ;

DUONG, TT ;

LEE, HY ;

MUNSON, PM ;

SMITH, AM ;

WAI, JM ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (16) :2300-2310