Design and synthesis of DNA-intercalating 9-fluoren-β-O-glycosides as potential IFN-inducers, and antiviral and cytostatic agents

被引：32

作者：

Alcaro, S

Arena, A

Neri, S

Ottanà, R

Ortuso, F

Pavone, B

Vigorita, MG

机构：

[1] Univ Messina, Fac Farm, Dipartimento Farmacochim, I-98168 Messina, Italy

[2] Fac Med & Chirurg, Microbiol Unit, Dipartimento Discipline Chirurg, I-98125 Messina, Italy

[3] Univ Catanzaro Magna Graecia, Dipartimento Sci Farmacobiol, I-88021 Roccelletta Di Borgia, Italy

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 07期

关键词：

D O I：

10.1016/j.bmc.2003.12.034

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel 9-fluoren-beta-O-glycosides, designed as DNA-intercalating agents in structural correlation with antiviral tilorone and anticancer anthracyclines, have been prepared with yields in beta-anomers ranging between 25 and 63%. They have been screened for antiproliferative, immunostimulating and antiviral properties against HSV-1 and HSV-2 viruses. Compounds displaying significant antiviral activity against HSV-2 are acetylated 1 and deprotected 6 9-fluorenyl-O-D-arabinopyranoses, whereas 9-fluorenyl-O-D-glucopyranose 3 is the most effective on HSV-1 replication, followed by 1 and 6. The conformational properties of these compounds have been evaluated by molecular modelling techniques. (C) 2004 Published by Elsevier Ltd.

引用

页码：1781 / 1791

页数：11

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