STRUCTURE AND STEREOCHEMISTRY OF THYSANONE - A NOVEL HUMAN RHINOVIRUS 3C-PROTEASE INHIBITOR FROM THYSANOPHORA-PENICILLOIDES

被引:69
作者
SINGH, SB [1 ]
CORDINGLEY, MG [1 ]
BALL, RG [1 ]
SMITH, JL [1 ]
DOMBROWSKI, AW [1 ]
GOETZ, MA [1 ]
机构
[1] MERCK SHARP & DOHME LTD,W POINT,PA 19486
关键词
THYSANONE; THYSANOPHORA-PENICILLOIDES; HRV 3C-PROTEASE INHIBITOR; NAPHTHOQUINONE-LACTOL;
D O I
10.1016/S0040-4039(00)92364-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structure of thysanone (1a), a novel naphthoquinone with a lactol ring was established on the basis of 1D and 2D NMR spectroscopy and confirmed by X-ray crystallographic analysis of the monomethyl ether (1b). Thysanone showed an IC50 of 13-mu-g/mL against HRV 3C-protease.
引用
收藏
页码:5279 / 5282
页数:4
相关论文
共 9 条
[1]   AN IMPROVED METHOD FOR HETERONUCLEAR CHEMICAL-SHIFT CORRELATION BY TWO-DIMENSIONAL NMR [J].
BAX, A ;
MORRIS, GA .
JOURNAL OF MAGNETIC RESONANCE, 1981, 42 (03) :501-505
[2]   INVESTIGATION OF COMPLEX NETWORKS OF SPIN-SPIN COUPLING BY TWO-DIMENSIONAL NMR [J].
BAX, A ;
FREEMAN, R .
JOURNAL OF MAGNETIC RESONANCE, 1981, 44 (03) :542-561
[3]   CORRELATION OF PROTON AND C-13 NMR-SPECTRA BY HETERONUCLEAR 2-DIMENSIONAL SPECTROSCOPY [J].
BODENHAUSEN, G ;
FREEMAN, R .
JOURNAL OF MAGNETIC RESONANCE, 1977, 28 (03) :471-476
[4]   CLEAVAGE OF SMALL PEPTIDES INVITRO BY HUMAN RHINOVIRUS 14-3C PROTEASE EXPRESSED IN ESCHERICHIA-COLI [J].
CORDINGLEY, MG ;
REGISTER, RB ;
CALLAHAN, PL ;
GARSKY, VM ;
COLONNO, RJ .
JOURNAL OF VIROLOGY, 1989, 63 (12) :5037-5045
[5]  
CORDINGLEY MG, 1990, J BIOL CHEM, V265, P9062
[6]  
GwaltneyJr JM, 1982, RHINOVIRUSES, P491
[7]  
KRAUSSLICH HG, 1988, ANNU REV BIOCHEM, V57, P701, DOI 10.1146/annurev.bi.57.070188.003413
[8]   PICORNAVIRAL PROCESSING - SOME NEW IDEAS [J].
PALMENBERG, AC .
JOURNAL OF CELLULAR BIOCHEMISTRY, 1987, 33 (03) :191-198
[9]   SPIRO INDOLINONE BETA-LACTAMS, INHIBITORS OF POLIOVIRUS AND RHINOVIRUS 3C-PROTEINASES [J].
SKILES, JW ;
MCNEIL, D .
TETRAHEDRON LETTERS, 1990, 31 (50) :7277-7280