Practical synthesis of unsymmetrical polyamine amides

被引：74

作者：

Blagbrough, IS ^{[1
]}

Geall, AJ ^{[1
]}

机构：

[1] Univ Bath, Dept Pharm & Pharmacol, Bath BA2 7AY, Avon, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 5-6期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)10542-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Desymmetrisation of readily available symmetrical polyamines is an important first step in the synthesis of many polyamine containing natural products. Likewise in the synthesis of polyamine amides which are potentially useful for gene delivery and as neuroprotectants, based upon channel blocking toxins found in certain wasp and spider venoms. The application of trifluoroacetyl as a protecting group allows unsymmetrical polyamine amides to be easily prepared on a gram scale. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：439 / 442

页数：4

共 39 条

[21] NEW CHEMISTRY OF NATURALLY-OCCURRING POLYAMINES [J].

GANEM, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (09) :290-298

[22] Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes [J].

Geall, AJ ;

Blagbrough, IS .

TETRAHEDRON LETTERS, 1998, 39 (5-6) :443-446

[23] Novel polyaminolipids enhance the cellular uptake of oligonucleotides [J].

GuyCaffey, JK ;

Bodepudi, V ;

Bishop, JS ;

Jayaraman, K ;

Chaudhary, N .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (52) :31391-31396

[24] Synthesis and pharmacological activity of philanthotoxin-343 analogs: Antagonists of ionotropic glutamate receptors [J].

Huang, DW ;

Jiang, H ;

Nakanishi, K ;

Usherwood, PNR .

TETRAHEDRON, 1997, 53 (37) :12391-12404

[25] FACILE SYNTHESIS OF 2'-AMINO-2'-DEOXYRIBOFURANOSYL PURINES [J].

IMAZAWA, M ;

ECKSTEIN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12) :2039-2041

[26] MONO-PROTECTED DIAMINES - N-TERT-BUTOXYCARBONYL-ALPHA,OMEGA-ALKANEDIAMINES FROM ALPHA,OMEGA-ALKANEDIAMINES [J].

KRAPCHO, AP ;

KUELL, CS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (16) :2559-2564

[27] POTASSIUM CHANNEL BLOCK BY CYTOPLASMIC POLYAMINES AS THE MECHANISM OF INTRINSIC RECTIFICATION [J].

LOPATIN, AN ;

MAKHINA, EN ;

NICHOLS, CG .

NATURE, 1994, 372 (6504) :366-369

[28] NEUROTOXIC ACYLPOLYAMINES FROM SPIDER VENOMS [J].

MCCORMICK, KD ;

MEINWALD, J .

JOURNAL OF CHEMICAL ECOLOGY, 1993, 19 (10) :2411-2451

[29] Total syntheses of polyamine amides PhTX-4.3.3 and PhTX-3.4.3: Reductive alkylation is a rapid, practical route to philanthotoxins [J].

Moya, E ;

Blagbrough, IS .

TETRAHEDRON LETTERS, 1995, 36 (51) :9401-9404

[30] PHILANTHOTOXIN-433 (PHTX-433), A NONCOMPETITIVE GLUTAMATE RECEPTOR INHIBITOR [J].

NAKANISHI, K ;

GOODNOW, R ;

KONNO, K ;

NIWA, M ;

BUKOWNIK, R ;

KALLIMOPOULOS, TA ;

USHERWOOD, P ;

ELDEFRAWI, AT ;

ELDEFRAWI, ME .

PURE AND APPLIED CHEMISTRY, 1990, 62 (07) :1223-1230

← 1 2 3 4 →