Structure based design:: Novel spirocyclic ethers as nonpeptidal P2-ligands for HIV protease inhibitors

被引：33

作者：

Ghosh, AK

Krishnan, K

Walters, DE

Cho, WH

Cho, H

Koo, Y

Trevino, J

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 | 1998年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0960-894X(98)00139-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel spirocyclic ethers were designed to function as nonpeptidal P-2-ligands for HIV-1 protease inhibitors. Incorporation of designed ligands in the (R)-(hydroxyethylamino)sulfonamide isostere afforded potent HIV protease inhibitors. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：979 / 982

页数：4

相关论文

共 19 条

[1] Evaluation of furofuran as a P-2 ligand for symmetry-based HIV protease inhibitors [J].

Chen, XQ ;

Li, L ;

Kempf, DJ ;

Sham, H ;

Wideburg, NE ;

Saldivar, A ;

Vasavanonda, S ;

Marsh, KC ;

McDonald, E ;

Norbeck, DW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (23) :2847-2852

[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] CRAM RULE SELECTIVITY IN THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF CHIRAL ALDEHYDES - A CONVENIENT ROUTE TO CHIRAL SYSTEMS OF BIOLOGICAL INTEREST [J].

DANISHEFSKY, S ;

KOBAYASHI, S ;

KERWIN, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1981-1983

[4] THE HIV-1 PROTEASE AS A THERAPEUTIC TARGET FOR AIDS [J].

DEBOUCK, C .

AIDS RESEARCH AND HUMAN RETROVIRUSES, 1992, 8 (02) :153-164

[5] STRUCTURE-BASED DESIGN OF HIV-1 PROTEASE INHIBITORS - REPLACEMENT OF 2 AMIDES AND A 10-PI-AROMATIC SYSTEM BY A FUSED BIS-TETRAHYDROFURAN [J].

GHOSH, AK ;

THOMPSON, WJ ;

FITZGERALD, PMD ;

CULBERSON, JC ;

AXEL, MG ;

MCKEE, SP ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (16) :2506-2508

[6] THE DEVELOPMENT OF CYCLIC SULFOLANES AS NOVEL AND HIGH-AFFINITY P(2) LIGANDS FOR HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

LEE, HY ;

THOMPSON, WJ ;

CULBERSON, C ;

HOLLOWAY, MK ;

MCKEE, SP ;

MUNSON, PM ;

DUONG, TT ;

SMITH, AM ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) :1177-1188

[7] 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

[8] Nonpeptidal P-2 ligands for HIV protease inhibitors: Structure-based design, synthesis, and biological evaluation [J].

Ghosh, AK ;

Kincaid, JF ;

Walters, DE ;

Chen, Y ;

Chaudhuri, NC ;

Thompson, WJ ;

Culberson, C ;

Fitzgerald, PMD ;

Lee, HY ;

McKee, SP ;

Munson, PM ;

Duong, TT ;

Darke, PL ;

Zugay, JA ;

Schleif, WA ;

Axel, MG ;

Lin, J ;

Huff, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) :3278-3290

[9] CYCLIC SULFONE-3-CARBOXAMIDES AS NOVEL P-2-LIGANDS FOR RO-31-8959 BASED HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

THOMPSON, WJ ;

MUNSON, PM ;

LIU, WM ;

HUFF, JR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (01) :83-88

[10] CYCLIC SULFOLANES AS NOVEL AND HIGH-AFFINITY P-2 LIGANDS FOR HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

THOMPSON, WJ ;

LEE, HY ;

MCKEE, SP ;

MUNSON, PM ;

DUONG, TT ;

DARKE, PL ;

ZUGAY, JA ;

EMINI, EA ;

SCHLEIF, WA ;

HUFF, JR ;

ANDERSON, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (07) :924-927