Synthesis and evaluation of 9-deoxy analogues of (-)-thysanone, an inhibitor of HRV 3C protease

被引：15

作者：

Jeong, Joo Young ^{[1
,2
]}

Sperry, Jonathan ^{[1
]}

Taylor, John A. ^{[2
]}

Brimble, Margaret A. ^{[1
,3
]}

机构：

[1] Univ Auckland, Sch Chem Sci, Auckland 1142, New Zealand

[2] Univ Auckland, Sch Biol Sci, Auckland 1010, New Zealand

[3] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, Auckland Mail Ctr, Auckland 1142, New Zealand

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 87卷

关键词：

HRV 3C protease; Inhibitor; Pyranonaphthoquinone; Thysanone; C-H activation; 3C-PROTEASE INHIBITOR; BIOLOGICAL EVALUATION; HUMAN RHINOVIRUSES; FORMAL SYNTHESIS; DEOXY ANALOGS; THYSANONE; EFFICIENT; STEREOCHEMISTRY; INFECTIONS; QUINONES;

D O I：

10.1016/j.ejmech.2014.09.063

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

9-Deoxy analogues of the HRV 3C protease inhibitor (-)-thysanone display better inhibitory properties than the natural product, inferring the C9-OH hinders binding to the enzyme. (C) 2014 Elsevier Masson SAS. All rights reserved.

引用

页码：220 / 227

页数：8

共 36 条

[1] Strategies towards the synthesis of 6-N,N-diethylcarbamyloxy-1,4-dimethoxy-7-naphthylboronic acid [J].

Ameer, F. ;

Green, I. R. ;

Krohn, K. ;

Sitoza, M. .

SYNTHETIC COMMUNICATIONS, 2007, 37 (18) :3041-3057

[2] Human rhinoviruses: coming in from the cold [J].

Arden, Katherine E. ;

Mackay, Ian M. .

GENOME MEDICINE, 2009, 1

[3] Chemoenzymatic synthesis of deoxy analogues of the DNA topoisomerase II inhibitor eleutherin and the 3C-protease inhibitor thysanone [J].

Bachu, Prabhakar ;

Sperry, Jonathan ;

Brimble, Margaret A. .

TETRAHEDRON, 2008, 64 (21) :4827-4834

[4] Isomerization of 7-Oxabenzonorbornadienes into Naphthols Catalyzed by [RuCl2(CO)3]2 [J].

Ballantine, Melissa ;

Menard, Michelle L. ;

Tam, William .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7570-7573

[5]

Brimble M., 2010, SYNTHESIS-STUTTGART, V2010, P2604

[6] Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone [J].

Brimble, MA ;

Elliott, RJR .

TETRAHEDRON, 2002, 58 (01) :183-189

[7] Synthesis of a regioisomeric analogue of the 3C-protease inhibitor thysanone via a Hauser annulation strategy [J].

Brimble, Margaret A. ;

Houghton, Scott I. ;

Woodgate, Paul D. .

TETRAHEDRON, 2007, 63 (04) :880-887

[8]

Brunble M., 2009, SYNTHESIS-STUTTGART, V2009, P2561

[9] Synthesis and absolute stereochemistry of thysanone [J].

Donner, CD ;

Gill, M .

TETRAHEDRON LETTERS, 1999, 40 (20) :3921-3924

[10]

Dormer C.D., 2002, J CHEM SOC P1, V1, P938

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