1,2,5,6-tetra-O-benzyl-D-mannitol derivatives as novel HIV protease inhibitors

被引：8

作者：

Bouzide, A ^{[1
]}

Sauvé, G ^{[1
]}

Sévigny, G ^{[1
]}

Yelle, J ^{[1
]}

机构：

[1] Pharmacor Inc, Laval, PQ H7V 3S8, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 20期

关键词：

D O I：

10.1016/S0960-894X(03)00677-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis and structure-activity relationships of HIV protease inhibitors derived from carbohydrate alditols are discussed. We disclose a new series of 1,2,5,6-tetra-O-alkyl-D-mannitol exhibiting sub-micromolar activity against HIV-protease. This series of inhibitors are non-nitrogen containing HIV-protease inhibitors and they are readily prepared in a few chemical steps from inexpensive commercially available starting materials. (C) 2003 Published by Elsevier Ltd.

引用

页码：3601 / 3605

页数：5

共 33 条

[21]

Mahler ME, 1997, SYNLETT, P193

[22]

MATAYOSHI ED, 1990, SCIENCE, V247, P957

[23] A SYNTHETIC HIV-1 PROTEASE INHIBITOR WITH ANTIVIRAL ACTIVITY ARRESTS HIV-LIKE PARTICLE MATURATION [J].

MCQUADE, TJ ;

TOMASSELLI, AG ;

LIU, L ;

KARACOSTAS, V ;

MOSS, B ;

SAWYER, TK ;

HEINRIKSON, RL ;

TARPLEY, WG .

SCIENCE, 1990, 247 (4941) :454-456

[24]

MOLLA A, 1998, J ANTIVIRAL RES, V1

[25] POSSIBLE MODEL FOR A NEW CHIRAL GLYCERIDE SYNTHESIS .1. SYNTHESIS OF 1-O-AROYL-2-O-TOSYL-SN-GLYCEROLS [J].

MORPAIN, C ;

TISSERAND, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1379-1383

[26] Structure-based design and synthesis of HIV-1 protease inhibitors employing β-D-mannopyranoside scaffolds [J].

Murphy, PV ;

O'Brien, JL ;

Gorey-Feret, LJ ;

Smith, AB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (13) :1763-1766

[27] Design and synthesis of potent C2-symmetric diol-based HIV-1 protease inhibitors:: Effects of fluoro substitution [J].

Pyring, D ;

Lindberg, J ;

Rosenquist, Å ;

Zuccarello, G ;

Kvarnström, I ;

Zhang, H ;

Vrang, L ;

Unge, T ;

Classon, B ;

Hallberg, A ;

Samuelsson, B .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (19) :3083-3091

[28] RATIONAL DESIGN OF PEPTIDE-BASED HIV PROTEINASE-INHIBITORS [J].

ROBERTS, NA ;

MARTIN, JA ;

KINCHINGTON, D ;

BROADHURST, AV ;

CRAIG, JC ;

DUNCAN, IB ;

GALPIN, SA ;

HANDA, BK ;

KAY, J ;

KROHN, A ;

LAMBERT, RW ;

MERRETT, JH ;

MILLS, JS ;

PARKES, KEB ;

REDSHAW, S ;

RITCHIE, AJ ;

TAYLOR, DL ;

THOMAS, GJ ;

MACHIN, PJ .

SCIENCE, 1990, 248 (4953) :358-361

[29]

SHAM HL, 1996, EXPERT OPIN INV DRUG, V5, P977

[30] X-ray crystallographic structure of ABT-378 (lopinavir) bound to HIV-1 protease [J].

Stoll, V ;

Qin, WY ;

Stewart, KD ;

Jakob, C ;

Park, C ;

Walter, K ;

Simmer, RL ;

Helfrich, R ;

Bussiere, D ;

Kao, J ;

Kempf, D ;

Sham, HL ;

Norbeck, DW .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2803-2806

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