Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

Stephen Hanessian; Jianchio Wang; Debra Montgomery; Vincent Stoll; Kent D. Stewart; Warren Kati; Clarence Maring; Dale Kempf; Charles Hutchins; W. Graeme Laver

doi:10.1016/S0960-894X(02)00732-1

Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

Stephen Hanessian^*, Jianchio Wang, Debra Montgomery, Vincent Stoll, Kent D. Stewart, Warren Kati, Clarence Maring, Dale Kempf, Charles Hutchins, W. Graeme Laver

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

Structure-based design has led to the synthesis of a novel analogue of GS-4071, an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (K_i=45 nM) bound to the active site shows that the vinyl group occupies the same subsite as the amino group in GS-4071.

Original language	English
Pages (from-to)	3425-3429
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	12
Issue number	23
DOIs	https://doi.org/10.1016/S0960-894X(02)00732-1
Publication status	Published - Dec 2002

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abstract = "Structure-based design has led to the synthesis of a novel analogue of GS-4071, an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (Ki=45 nM) bound to the active site shows that the vinyl group occupies the same subsite as the amino group in GS-4071.",

author = "Stephen Hanessian and Jianchio Wang and Debra Montgomery and Vincent Stoll and Stewart, {Kent D.} and Warren Kati and Clarence Maring and Dale Kempf and Charles Hutchins and Laver, {W. Graeme}",

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AU - Hanessian, Stephen

AU - Wang, Jianchio

AU - Montgomery, Debra

AU - Stoll, Vincent

AU - Stewart, Kent D.

AU - Kati, Warren

AU - Maring, Clarence

AU - Kempf, Dale

AU - Hutchins, Charles

AU - Laver, W. Graeme

PY - 2002/12

Y1 - 2002/12

N2 - Structure-based design has led to the synthesis of a novel analogue of GS-4071, an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (Ki=45 nM) bound to the active site shows that the vinyl group occupies the same subsite as the amino group in GS-4071.

AB - Structure-based design has led to the synthesis of a novel analogue of GS-4071, an influenza neuraminidase inhibitor, in which the basic amino group has been replaced by a hydrophobic vinyl group. An X-ray co-crystal structure of the new inhibitor (Ki=45 nM) bound to the active site shows that the vinyl group occupies the same subsite as the amino group in GS-4071.

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U2 - 10.1016/S0960-894X(02)00732-1

DO - 10.1016/S0960-894X(02)00732-1

M3 - Article

SN - 0960-894X

VL - 12

SP - 3425

EP - 3429

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm

Abstract

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