流感病毒神经氨酸酶抑制剂的研究进展
作者：李璟;陈;孙雅博;黄永茂;范继业;
Author：
收稿日期： 年卷（期）页码：2015,30(01):-113-116
期刊名称：华西药学杂志
Journal Name：WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字：唾液酸;神经氨酸酶;抑制剂;流感;病毒;合成;研究进展;综述
Key words：
基金项目：
中文摘要
流感病毒在感染和传播过程中,神经氨酸酶(NA)起到了关键作用,因此,神经氨酸(即唾液酸)已成为设计、合成流感病毒神经氨酸酶抑制剂(NAIs)的重要先导化合物和模版分子。文中综述了抗流感病毒唾液酸类NAIs的研究进展。
参考文献
[1]黄兰,周剑芳,韦红,等.流感病毒神经氨酸酶抑制剂药物耐药现状及机制研究进展[J].病毒学报,2012,28(5):572-576.
[2]Calfee D,Hayden F.New approaches to influenza chemotherapy neuraminidase inhibitors[J].Drugs,1998,56(4):537-553.
[3]Meindl P,Bodo G,Lindner J,et al.Einfluss von 2-desoxy-2,3-dehydro-N-acetylneuramins ure auf myxovirus-neuraminidasen und die replikation von influenza-und newcastle disease virus[J].Z Narurforsch B,1971,26(8):792-797.
[4]Goodford PJ.A computational procedure for determining energetically favorable binding sites on biologically important macromolecules[J].J Med Chem,1985,28(7):849-857.
[5]Kim CU,Lew W,Williams MA,et al.Design,synthesis,and structural analysis of carbocyelic sialic acid analogues with potent anti-influenza activity[J].J Am Chem Soc,1997,119(4):681-690.
[6]Marek JJ,Singh S,Brouillette WJ,et al.Struetures of aromatic inhibitors of influenza virus neuraminidase[J].Biochemistry,1995,34(10):3144-3151.
[7]Williams M,Bischofberger N,Swaminathan S,et al.Synthesis and influenza neuraminidase inhibitory activity of aromatic analogues of sialic acid[J].Bioorg Med Chem Lett,1995,5(19):2251-2254.
[8]Singh S,Jedrzejas MJ,Air GM,et al.Structure-based inhibitors of influenza virus sialidase.A benzoic acid lead with novel interaction[J].J Med Chem,1995,38(17):3217-3225.
[9]Chand P,Babu YS,Bantia S,et al.Design and synthesis of benzoic acid derivatives as influenza neuraminidase inhibitors using structure-based drug design[J].J Med Chem,1997,40(25):4030-4052.
[10]Atigadda VR,Brouillette WJ,Duarte F,et al.Potent inhibition of influenza sialidase by a benzoic acid containing a 2-pyrmlidine substituent[J].J Med Chem,1999,42(13):2332-2343.
[11]Mack H,Brossmer R.Synthesis of 6-thiosialic acids and 6-thio-N-acetyl-D-neuraminic acid[J].Telra Lett,1987,28(2):191-194.
[12]Parr IB,Horenstein BA.New electronic analogs of the sialyl cation:N-functionalized 4-acetamido-2,4-dihydroxypiperidines.Inhibition of bacterial sialidases[J].J Org Chem,1997,62(21):7459-7494.
[13]Hanessian S,Rogel O.Synthesis of glyeophostones:Cyclic phosphonate analogues of biologically relevant sugars[J].J Org Chem,2000,65(9):2667-2674.
[14]Zhang LJ,Williams MA,Mendel DB,et al.Synthesis and evaluation of l,4,5,6-tetrarydropyridazine derivatives as influenza neuraminidase inhibitors[J].Bioorg Med Chem Lett,1999,9(13):1751-1756.
[15]Shitara E,Nishimura Y,Nerome K,et al.Synthesis of 6-acetamido-5-amino-and-5-guanidino-3,4-dehydro-N-(2-ethylbutyryl)-3-piperidine-carboxylic acids related to Zanamivir and Oseltamivir,Inhibitors of influenza virus neuraminidases[J].Org Lett,2000,2(24):3837-3840.
[16]Kati WM,Montgomery D,Maring C,et al.Novel alpha-and beta-amino acid inhibitors of influenza virus neuraminidase[J].Antimicro Agents Chemother,2001,45(9):2563-2570.
[17]Chand P,Kotian PL,Morris PE,et al.Synthesis and inhibitory activity of benzoic acid and pyridine derivatives on influenza neuraminidase[J].Bioorg Med Chem,2005,13(7):2665-2678.
[18]Wang GT,Wang S,Gentles R,et al.Design,synthesis,and struetural analysis of inhibitors of influenza neuranunidase containing a 2,3-disubstituted tetrahydrofuran-5-carboxylic acid core[J].Bioorg Med Chem Lett,2005,15(l):125-128.
[19]Babu YS,Chand P,Bantia S,et al.BCX-1812(RWJ-270201):Discovery of a novel,highly potent,orally active,and selective influenza neuraminidase inhibitor through structurebased drug design[J].J Med Chem,2000,43:3482-3486.
[20]Chand P,Kotian PL,Dehghani A,et al.Systematic structurebased design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity[J].J Med Chem,2001,44:4379-4392.
[21]Wang GT,Chen Y,Wang S,et al.Design,synthesis,and structural analysis of influenza neuraminidase inhibitors containing pyrrolidine cores[J].J Med Chem,2001,44:1192-1201.
[22]Kati WM,Montgomery D,Carriek R,et al.In vitro characterization of A-315675,a highly potent inhibitor of A and B strain influenza virus neuraminidases and influenza virus replication[J].Antimicrob Agents Chemorher,2002,46(4):1014-1021.
[23]Shie JJ,Fang JM,Wong CH,et al.Synthesis of tamiflu and its phosphonate congeners possessing potent anti-influenza activity[J].J Am Chem Soc,2007,129:11892-11893.
[24]Honda T,Yoshida S,Arai M,et al.Synthesis and anti-influenza evaluation of polyvalent sialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives[J].Bioorg Chem Lett,2002,12(15):1929-1932.
[25]Macdonald SJF,Cameron R,Demaine DA,et al.Dimeric Zanamivir conjugates with various linking groups are potent,longlasting lnhibitors of influenza neuraminidase ineluding H5N1avian influenza[J].J Medicinal Chemistry,2005,48(8):2964-2971.
[26]Watson KG,Cameron R,Fenton RJ,et al.Highly potent and long-acting trimeric and tetrameric inhibitors of influenza virus neuraminidase[J].Bioorg Med Chem Lett,2004,14:1589-1592.
[27]Wen WH,Lin M,Su CY,et al.Synergistic effect of Zanamivir-porphyrin conjugates on inhibition of neuraminidase and inactivation of influenza virus[J].J Med Chem,2009,52:4903-4910.
[28]Russell RJ,Haire LF,Stevens DJ,et al.The structure of H5N1avian influenza neuraminidase suggests new opportunities for drug design[J].Nature,2006,443:45-49.
[29]Du QS,Wang SQ,Chou KC.Analogue inhibitors by modifying oseltamivir based on the crystal neuraminidase strueture for treating drug-resistant H5N1 virus[J].Biochem Biophysi Res Commun,2007,362(2):525-531.
[30]Mitrasinovie PM.On the structure-based design of novel inhibitors of H5N1 influenza avirus neuraminidase(NA)[J].Biophys Chem,2009,140(l-3):35-38.
[31]Dursi P,Chiappori F,Merelli I,et a1.Virtual screening pipeline and ligand modelling for H5N1neuraminidase[J].Biochem Biophs Res Commun,2009,383(4):445-449.
[32]Li Y,Zhou B,Wang R.Rational design of Tamitlu derivatives targeting at the open conformation of nettraminidase subtype 1[J].J Mol Graph Model,2009,28(3):203-219.
[33]Sun C,Zhang X,Huang H,et al.Synthesis and evaluation of a new series of substituted acyl(thio)urea and thiadiazolo[2,3-a]pyrimidine derivatives as potent inhibitors of influenza virus neuraminidase[J].Bioorg Med Chem,2006,14(24):8574-8581.
[34]An J,Lee DCW,Law AHY,et al.A novel small-molceule inhibitor of the avian influenza H5N1virus determined through computational screening against the neuraminidase[J].J Medicinal Chemistry,2009,52(9):2667-2672.
[35]Amaro RE.Mechanism of 150-cavity formation in influenza neuraminidase[J].Nat Commun,2:388.
[36]Santosh R,Jeffrey CD,Andrea M,et al.Novel 3,4-disubstitutedNeu5Ac2en derivatives as probes to investigate flexibility of the influenza virus sialidase 150-loop[J].Bioorg Med Chem,2013,21(16):4820-4830.
【关闭】
