SYNTHESIS AND PROPERTIES OF 6A-AMINO-6A-DEOXY-ALPHA AND 6A-AMINO-6A-DEOXY-BETA-CYCLODEXTRIN

被引:64
作者
BROWN, SE [1 ]
COATES, JH [1 ]
COGHLAN, DR [1 ]
EASTON, CJ [1 ]
VANEYK, SJ [1 ]
JANOWSKI, W [1 ]
LEPORE, A [1 ]
LINCOLN, SF [1 ]
LUO, Y [1 ]
MAY, BL [1 ]
SCHIESSER, DS [1 ]
WANG, P [1 ]
WILLIAMS, ML [1 ]
机构
[1] UNIV ADELAIDE, DEPT CHEM, GPO BOX 498, ADELAIDE, SA 5001, AUSTRALIA
关键词
D O I
10.1071/CH9930953
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The monotosylates obtained by treatment of alpha- and beta-cyclodextrin with p-methylbenzenesulfonyl chloride reacted with ammonia to give the title compounds. These amines are of unusually low basicity, with pK(a) values of 8.70 and 8.72, respectively. In water at 25-degrees, the hydrochloride salt of the amine derived from beta-cyclodextrin is approximately 40 times more soluble than beta-cyclodextrin and, through complexation, the salt increases the solubility of Nabumetone over 800 times.
引用
收藏
页码:953 / 958
页数:6
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