Simple syntheses of cyclic polyamines using selectively N-tritylated polyamines and succinic anhydride

被引:14
作者
Militsopoulou, M [1 ]
Tsiakopoulos, N [1 ]
Chochos, C [1 ]
Magoulas, G [1 ]
Papaioannou, D [1 ]
机构
[1] Univ Patras, Dept Chem, GR-26500 Patras, Greece
关键词
spermine; spermidine; cyclic anhydride; cyclic polyamine; trityl group;
D O I
10.1016/S0040-4039(02)00335-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of selectively N-tritylated spermidine and spermine derivatives with succinic anhydride, followed by PyBrOP-mediated intramolecular amide bond formation and LiAlH4 reduction, allows for an easy and general entry to cyclic polyamine derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2593 / 2596
页数:4
相关论文
共 26 条
[1]   Solid-phase synthesis of bis-cyclic guanidines from tripeptides [J].
Acharya, AN ;
Ostresh, JM ;
Houghten, RA .
TETRAHEDRON, 2001, 57 (50) :9911-9914
[2]   The synthesis of L-proline derived tetraazamacrocyclic ligands of C2 symmetry via intramolecular ester aminolysis [J].
Achmatowicz, M ;
Jurczak, J .
TETRAHEDRON-ASYMMETRY, 2001, 12 (01) :111-119
[3]   The synthesis of L-proline derived hexaazamacrocyclic ligands of C3 symmetry via intramolecular methyl ester aminolysis [J].
Achmatowicz, M ;
Jurczak, J .
TETRAHEDRON-ASYMMETRY, 2001, 12 (03) :487-495
[4]   ASYMMETRIC-SYNTHESIS OF HIGHLY FUNCTIONALIZED POLYAZAMACROCYCLES VIA REDUCTION OF CYCLIC PEPTIDE PRECURSORS [J].
ASTON, KW ;
HENKE, SL ;
MODAK, AS ;
RILEY, DP ;
SAMPLE, KR ;
WEISS, RH ;
NEUMANN, WL .
TETRAHEDRON LETTERS, 1994, 35 (22) :3687-3690
[5]   PRACTICAL SYNTHESIS OF THE PUTATIVE POLYAMINE SPIDER TOXIN FTX - A PROPOSED BLOCKER OF VOLTAGE-SENSITIVE CALCIUM CHANNELS [J].
BLAGBROUGH, IS ;
MOYA, E .
TETRAHEDRON LETTERS, 1994, 35 (13) :2057-2060
[6]   Cheno-, urso- and deoxycholic acid spermine conjugates: Relative binding affinities for calf thymus DNA [J].
Blagbrough, IS ;
Al-Hadithi, D ;
Geall, AJ .
TETRAHEDRON, 2000, 56 (21) :3439-3447
[7]  
BLAGBROUGH IS, 1997, PHARM SCI, V3, P223
[8]   CYCLOPOLYAMINES - SYNTHESIS OF CYCLOSPERMIDINES AND CYCLOSPERMINES, ANALOGS OF SPERMIDINE AND SPERMINE [J].
BRAND, G ;
HOSSEINI, MW ;
RUPPERT, R .
TETRAHEDRON LETTERS, 1994, 35 (46) :8609-8612
[9]   Homologation of polyamines in the rapid synthesis of lipospermine conjugates and related lipoplexes [J].
Geall, AJ ;
Blagbrough, IS .
TETRAHEDRON, 2000, 56 (16) :2449-2460
[10]  
Karigiannis G, 2000, EUR J ORG CHEM, V2000, P1841