A novel solid-phase reductive alkylation route to acridine and dansyl polyamine conjugates

被引:20
作者
Carrington, S
Renault, J
Tomasi, S
Corbel, JC
Uriac, P
Blagbrough, IS [1 ]
机构
[1] Univ Bath, Dept Pharm & Pharmacol, Bath BA2 7AY, Avon, England
[2] Univ Rennes 1, Fac Pharm, F-35043 Rennes, France
关键词
D O I
10.1039/a904023d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Solid-phase organic synthesis (SPOS) routes to target unsymmetrical polyamines and their acridinyl and dansyl conjugates have been developed based upon borane-pyridine complex (BAP) mediated reductive alkylation, azide reduction with triphenylphosphine, and the use of pent-4-enoyl (Pnt) as an orthogonal amine protecting group.
引用
收藏
页码:1341 / 1342
页数:2
相关论文
共 29 条
[1]   Asymmetric intercalation of N1-(acridin-9-ylcarbonyl)spermine at homopurine sites of duplex DNA [J].
Blagbrough, IS ;
Taylor, S ;
Carpenter, ML ;
Novoselskiy, V ;
Shamma, T ;
Haworth, IS .
CHEMICAL COMMUNICATIONS, 1998, (08) :929-930
[2]  
BLAGBROUGH IS, 1997, PHARM SCI, V3, P223
[3]   SYNTHESIS OF THE SPIDER TOXINS NEPHILATOXIN-9 AND NEPHILATOXIN-11 BY A NOVEL SOLID-PHASE STRATEGY [J].
BYCROFT, BW ;
CHAN, WC ;
HONE, ND ;
MILLINGTON, S ;
NASH, IA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7415-7416
[4]   One pot synthesis of unsymmetrically functionalized polyamines by a solid phase strategy starting from their symmetrical polyamine-counterparts. [J].
Byk, G ;
Frederic, M ;
Scherman, D .
TETRAHEDRON LETTERS, 1997, 38 (18) :3219-3222
[5]   Synthesis, activity, and structure-activity relationship studies of novel cationic lipids for DNA transfer [J].
Byk, G ;
Dubertret, C ;
Escriou, V ;
Frederic, M ;
Jaslin, G ;
Rangara, R ;
Pitard, B ;
Crouzet, J ;
Wils, P ;
Schwartz, B ;
Scherman, D .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (02) :224-235
[6]   CHEMOSELECTIVITY OF THE REACTION OF DICHLOROBORANES WITH FUNCTIONAL AZIDES - EFFICIENT FUNCTIONALIZED SECONDARY AMINE SYNTHESIS [J].
CARBONI, B ;
VAULTIER, M ;
CARRIE, R .
TETRAHEDRON, 1987, 43 (08) :1799-1810
[7]   ALIPHATIC AMINO AZIDES AS KEY BUILDING-BLOCKS FOR EFFICIENT POLYAMINE SYNTHESES [J].
CARBONI, B ;
BENALIL, A ;
VAULTIER, M .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3736-3741
[8]   Macrocyclic polyamine lactam synthesis by diphenyl ether closure of 23-, 24- and 28-membered rings [J].
Carrington, S ;
Fairlamb, AH ;
Blagbrough, IS .
CHEMICAL COMMUNICATIONS, 1998, (21) :2335-2336
[9]   N-1-dansyl-spermine and N-1-(n-octanesulfonyl)-spermine, novel glutamate receptor antagonists: Block and permeation of N-methyl-D-aspartate receptors [J].
Chao, J ;
Seiler, N ;
Renault, J ;
Kashiwagi, K ;
Masuko, T ;
Igarashi, K ;
Williams, K .
MOLECULAR PHARMACOLOGY, 1997, 51 (05) :861-871
[10]   SYNTHESIS AND ASSAY OF HYBRID ANALOGS OF ARGIOTOXIN-636 AND PHILANTHOTOXIN-433 - GLUTAMATE-RECEPTOR ANTAGONISTS [J].
CHOI, SK ;
NAKANISHI, K ;
USHERWOOD, PNR .
TETRAHEDRON, 1993, 49 (26) :5777-5790