The "triamino-analogue" of methyl cholate; A facial amphiphile and scaffold with potential for combinatorial and molecular recognition chemistry

被引:48
作者
Broderick, S [1 ]
Davis, AP [1 ]
Williams, RP [1 ]
机构
[1] Trinity Coll, Dept Chem, Dublin 2, Ireland
关键词
D O I
10.1016/S0040-4039(98)01254-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The triamino steroid 2 is synthesized from cholic acid (1), and found to possess little tendency to aggregate at pH 5 - 6 in aqueous solution. 2 and/or related derivatives are expected to find use in the synthesis of receptors and combinatorial libraries, and as "contrafacial amphiphiles" for drug delivery across cell membranes. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6083 / 6086
页数:4
相关论文
共 26 条
[1]   BISQUATERNARY AMMONIUM SALTS DERIVED FROM 3ALPHA,12ALPHA-DIAMINO-5BETA-CHOLANE AND 3ALPHA,12ALPHA-DIAMINO-24-NOR-5BETA-CHOLANE [J].
AHMED, S ;
ALAUDDIN, M ;
CADDY, B ;
MARTINSM.M ;
SIDWELL, WTL ;
WATSON, TR .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (03) :521-&
[2]  
BATTA AK, 1991, J LIPID RES, V32, P977
[3]   PEPTIDOSTEROIDAL RECEPTORS FOR OPIOID-PEPTIDES - SEQUENCE-SELECTIVE BINDING USING A SYNTHETIC RECEPTOR LIBRARY [J].
BOYCE, R ;
LI, G ;
NESTLER, HP ;
SUENAGA, T ;
STILL, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7955-7956
[4]   FACIAL AMPHIPHILES [J].
CHEN, Y ;
HO, DM ;
GOTTLIEB, CR ;
KAHNE, D ;
BRUCK, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7319-7320
[5]   Sequence-selective peptide binding with a peptido-A,B-trans-steroidal receptor selected from an encoded combinatorial receptor library [J].
Cheng, YA ;
Suenaga, T ;
Still, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (07) :1813-1814
[6]   Anion recognition by tripodal receptors derived from cholic acid [J].
Davis, AP ;
Perry, JJ ;
Williams, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1793-1794
[7]   CHOLAPHANES ET-AL - STEROIDS AS STRUCTURAL COMPONENTS IN MOLECULAR ENGINEERING [J].
DAVIS, AP .
CHEMICAL SOCIETY REVIEWS, 1993, 22 (04) :243-253
[8]   Mitsunobu reactions with methanesulfonic acid; The replacement of equatorial hydroxyl groups by azide with net retention of configuration [J].
Davis, AP ;
Dresen, S ;
Lawless, LJ .
TETRAHEDRON LETTERS, 1997, 38 (24) :4305-4308
[9]   STEREOCONTROLLED SYNTHESIS OF CHOLIC-ACID DERIVATIVES WITH N-PROTECTED 7-BETA-AMINO AND OR 12-BETA-AMINO SUBSTITUENTS [J].
DAVIS, AP ;
ORCHARD, MG .
TETRAHEDRON LETTERS, 1992, 33 (35) :5111-5112
[10]  
DAVIS AP, 1996, COMPREHENSIVE SUPRAM, V4, P257