Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents

被引：59

作者：

Johnson, HA ^{[1
]}

Thomas, NR ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 02期

关键词：

D O I：

10.1016/S0960-894X(01)00719-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p- phenoxy] and 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-benzyloxy] propanes is reported. These compounds have been prepared to investigate the potential of incorporating iminosugars as useful recognition elements in DNA minor groove binding agents. The compounds were shown to have very moderate binding affinities for DNA in thermal denaturation and ethidium bromide displacement assays when compared with propamidine. They were also found to possess some in vitro anticancer activity that did not correlate with their DNA binding affinity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：237 / 241

页数：5

共 19 条

[11]

Lohray BB, 1999, INDIAN J CHEM B, V38, P1311

[12] POLYHYDROXYLATED PIPERIDINES AND AZEPANES FROM D-MANNITOL - SYNTHESIS OF 1-DEOXYNOJIRIMYCIN AND ANALOGS [J].

POITOUT, L ;

LEMERRER, Y ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1994, 35 (20) :3293-3296

[13] C-2-symmetrical tetrahydroxyazepanes as inhibitors of glycosidases and HIV/FIV proteases [J].

Qian, XH ;

MorisVaras, F ;

Fitzgerald, MC ;

Wong, CH .

BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (12) :2055-2069

[14]

Qian XH, 1996, BIOORG MED CHEM LETT, V6, P1117

[15] Synthetic DNA minor groove-binding drugs [J].

Reddy, BSP ;

Sondhi, SM ;

Lown, JW .

PHARMACOLOGY & THERAPEUTICS, 1999, 84 (01) :1-111

[16]

Uchida R, 1999, CHEM PHARM BULL, V47, P187

[17] NMR CHARACTERIZATION OF CALICHEAMICIN GAMMA(1)(I) BOUND TO DNA [J].

WALKER, SL ;

ANDREOTTI, AH ;

KAHNE, DE .

TETRAHEDRON, 1994, 50 (05) :1351-1360

[18] 1,5-bis(4-amidinophenoxy)pentane (pentamidine) is a potent inhibitor of [3H]idazoxan binding to imidazoline I2 binding sites [J].

Wood, DH ;

Hall, JE ;

Rose, BG ;

Tidwell, RR .

EUROPEAN JOURNAL OF PHARMACOLOGY, 1998, 353 (01) :97-103

[19] Design of an oligosaccharide scaffold that binds in the minor groove of DNA [J].

Xuereb, H ;

Maletic, M ;

Gildersleeve, J ;

Pelczer, I ;

Kahne, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (09) :1883-1890

← 1 2 →