Improved preparation of perallylated cyclodextrins: facile synthesis of cyclodextrin-based polycationic and polyanionic compounds.
An improved procedure for the perallylation of cyclodextrins allowed the preparation of O-perallylated alpha-, beta-, and gamma-cyclodextrins in 89, 91, and 88% yields, respectively. These were converted into two cyclodextrin-based functionalized compounds, the polycationic heptakis[2,3,6-tri-O-(6-amino-3-thiahexyl)]-beta-cyclodextrin hydrochloride (3), and the polyanionic heptakis[2,3,6-tri-O-(sodium 5-carboxyl-3-thiapentyl)]-beta-cyclodextrin (4), a potential inhibitor of HIV-1 replication.
Ni
Jiahong
J
Institute of Human Virology, University of Maryland Biotechnology Institute, University of Maryland, 725 W. Lombard Street, Baltimore, MD 21201, USA.
Singh
Suddham
S
Wang
Lai-Xi
LX
D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D011073:Polyamines / Q000138:chemical synthesis* / Q000737:chemistry; D000071228:Polyelectrolytes; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry
D019380:Anti-HIV Agents; D003505:Cyclodextrins; D011073:Polyamines; D000071228:Polyelectrolytes; D011108:Polymers; C457440:heptakis(2,3,6-tri-O-(sodium 5-carboxyl-3-thiapentyl))-cyclodextrin