Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

Jie Zhang; Qiang Wang; Hao Fang; Wenfang Xu; Ailin Liu; Guanhua Du

doi:10.1016/j.bmc.2007.01.020

Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

Jie Zhang
, Qiang Wang
, Hao Fang
, Wenfang Xu
, Ailin Liu
, Guanhua Du

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

29 Scopus citations

Abstract

A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroxy-l-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC₅₀ = 1.56-2.71 μM) which are compared to that the NA inhibitor Oseltamivir (IC₅₀ = 1.06 μM), and could be used as lead compoundS in the future.

Original language	English
Pages (from-to)	2749-2758
Number of pages	10
Journal	Bioorganic and Medicinal Chemistry
Volume	15
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2007.01.020
State	Published - 1 Apr 2007
Externally published	Yes

Keywords

Neuraminidase inhibitor
Peptidomimetics
Pyrrolidine derivatives
SAR study

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10.1016/j.bmc.2007.01.020

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title = "Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors",

abstract = "A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroxy-l-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 μM) which are compared to that the NA inhibitor Oseltamivir (IC50 = 1.06 μM), and could be used as lead compoundS in the future.",

keywords = "Neuraminidase inhibitor, Peptidomimetics, Pyrrolidine derivatives, SAR study",

author = "Jie Zhang and Qiang Wang and Hao Fang and Wenfang Xu and Ailin Liu and Guanhua Du",

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T1 - Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

AU - Zhang, Jie

AU - Wang, Qiang

AU - Fang, Hao

AU - Xu, Wenfang

AU - Liu, Ailin

AU - Du, Guanhua

PY - 2007/4/1

Y1 - 2007/4/1

N2 - A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroxy-l-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 μM) which are compared to that the NA inhibitor Oseltamivir (IC50 = 1.06 μM), and could be used as lead compoundS in the future.

AB - A series of pyrrolidine derivatives were synthesized and evaluated for their ability to inhibit neuraminidase (NA) of influenza A virus (H3N2). All compounds were synthesized in good yields starting from commercially 4-hydroxy-l-proline using a suitable synthetic strategy. These compounds showed potent inhibitory activity against influenza A neuraminidase. Within this series, five compounds, 6e, 9c, 9e, 9f, and 10e, have good potency (IC50 = 1.56-2.71 μM) which are compared to that the NA inhibitor Oseltamivir (IC50 = 1.06 μM), and could be used as lead compoundS in the future.

KW - Neuraminidase inhibitor

KW - Peptidomimetics

KW - Pyrrolidine derivatives

KW - SAR study

UR - https://www.scopus.com/pages/publications/33847636143

U2 - 10.1016/j.bmc.2007.01.020

DO - 10.1016/j.bmc.2007.01.020

M3 - 文章

C2 - 17287121

AN - SCOPUS:33847636143

SN - 0968-0896

VL - 15

SP - 2749

EP - 2758

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 7

ER -

Design, synthesis, inhibitory activity, and SAR studies of pyrrolidine derivatives as neuraminidase inhibitors

Abstract

Keywords

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