A FACILE SYNTHESIS OF 2-SUBSTITUTED N-TERT-BUTOXYCARBONYL-N-METHYL-1,3-PROPANEDIAMINES, KEY INTERMEDIATES FOR THE PREPARATION OF TRIPLEX DNA-SPECIFIC INTERCALATORS

被引:13
作者
STREKOWSKI, L [1 ]
GULEVICH, Y [1 ]
VANAKEN, K [1 ]
WILSON, DW [1 ]
FOX, KR [1 ]
机构
[1] UNIV SOUTHAMPTON,DEPT PHYSIOL & PHARMACOL,SOUTHAMPTON SO9 3TU,HANTS,ENGLAND
关键词
D O I
10.1016/0040-4039(94)02228-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-substituted 2-(2-naphthyl)quinolin-4-amines 4b,c are superior to other DNA intercalators reported to date in the ability to selectively stabilize triple helix DNA in the presence of duplex DNA. A facile synthesis of the title diamines 1 required for the preparation of 4 is based on a novel addition reaction of metallated tert-butyl N,N-dimethylcarbamate [Boc-N(Me)CH(2)M; 7, M=Li; 8, M=MgBr; 9, M=Cu(CN)ZnCl] with a nitroalkene.
引用
收藏
页码:225 / 228
页数:4
相关论文
共 14 条
[11]   RECENT PROGRESS USING CHIRAL FORMAMIDINES IN ASYMMETRIC SYNTHESES [J].
MEYERS, AI .
TETRAHEDRON, 1992, 48 (13) :2589-2612
[12]  
ROSINI G, 1988, SYNTHESIS-STUTTGART, P833
[13]   THE O-AMINO-TRIFLUOROMETHYL FUNCTIONALITY AS A NOVEL SYNTHON FOR 4-FLUOROQUINOLINES [J].
STREKOWSKI, L ;
KISELYOV, AS ;
HOJJAT, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :5886-5890
[14]   DNA TRIPLE-HELIX SPECIFIC INTERCALATORS AS ANTIGENE ENHANCERS - UNFUSED AROMATIC CATIONS [J].
WILSON, WD ;
TANIOUS, FA ;
MIZAN, S ;
YAO, SJ ;
KISELYOV, AS ;
ZON, G ;
STREKOWSKI, L .
BIOCHEMISTRY, 1993, 32 (40) :10614-10621