An efficient synthesis of mimetics of neamine for RNA recognition

被引:36
作者
Ding, YL [1 ]
Hofstadler, SA [1 ]
Swayze, EE [1 ]
Griffey, RH [1 ]
机构
[1] ISIS Pharmaceut, Carlsbad, CA 92008 USA
关键词
D O I
10.1021/ol015794g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] As mimetics of neamine, several 4-heterocyclic 2-deoxystreptamine derivatives were chemically synthesized for RNA recognition. Conversion of 4-methylthiomethyl-5,6-di-O-acetyl-diazido-2-deoxystreptamine to the 4-chloromethyl derivative followed by reactions with different nuclophilic reagents gave the 4-heterocyclic 2-deoxystreptamine derivatives in satisfactory yields.
引用
收藏
页码:1621 / 1623
页数:3
相关论文
共 19 条
[1]  
COREY EJ, 1982, J AM CHEM SOC, V104, P6818, DOI 10.1021/ja00388a074
[2]   AN INEXPENSIVE AND CONVENIENT PREPARATION OF METHOXYMETHYL AND PHENYLTHIOMETHYL ETHERS [J].
DIETER, RK ;
DATAR, R .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (01) :63-70
[3]   A cationic cyclophane that forms a base-pair open complex with RNA duplexes [J].
FernandezSaiz, M ;
Schneider, HJ ;
Sartorius, J ;
Wilson, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) :4739-4745
[4]   Design and synthesis of new aminoglycoside antibiotics containing neamine as an optimal core structure: Correlation of antibiotic activity with in vitro inhibition of translation [J].
Greenberg, WA ;
Priestley, ES ;
Sears, PS ;
Alper, PB ;
Rosenbohm, C ;
Hendrix, M ;
Hung, SC ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6527-6541
[5]   Determinants of aminoglycoside-binding specificity for rRNA by using mass spectrometry [J].
Griffey, RH ;
Hofstadler, SA ;
Sannes-Lowery, KA ;
Ecker, DJ ;
Crooke, ST .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (18) :10129-10133
[6]  
Hooper I.R., 1982, Aminoglycoside Antibotic
[7]   DESIGN AND SYNTHESIS OF RNA-SPECIFIC GROOVE-BINDING CATIONS - IMPLICATIONS FOR ANTIVIRAL DRUG DESIGN [J].
MCCONNAUGHIE, AW ;
SPYCHALA, J ;
ZHAO, M ;
BOYKIN, D ;
WILSON, WD .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) :1063-1069
[8]   Discovery of selective, small-molecule inhibitors of RNA complexes .2. Self-splicing group I intron ribozyme [J].
Mei, HY ;
Cui, M ;
Lemrow, SM ;
Czarnik, AW .
BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (06) :1185-1195
[9]   INHIBITION OF AN HIV-1 TAT-DERIVED PEPTIDE BINDING TO TAR RNA BY AMINOGLYCOSIDE ANTIBIOTICS [J].
MEI, HY ;
GALAN, AA ;
HALIM, NS ;
MACK, DP ;
MORELAND, DW ;
SANDERS, KB ;
TRUONG, HN ;
CZARNIK, AW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (22) :2755-2760
[10]   INTERACTION OF ANTIBIOTICS WITH FUNCTIONAL SITES IN 16S RIBOSOMAL-RNA [J].
MOAZED, D ;
NOLLER, HF .
NATURE, 1987, 327 (6121) :389-394