Synthesis and in vivo biological activity of large-ringed calixarenes against Mycobacterium tuberculosis

被引：21

作者：

Goodworth, Kerry J. ^{[1
]}

Herve, Anne-Cecile ^{[1
]}

Stavropoulos, Evangelos ^{[2
]}

Herve, Gwenaelle ^{[1
]}

Casades, Isabel ^{[1
,2
]}

Hill, Alison M. ^{[3
]}

Weingarten, Gordon G. ^{[4
]}

Tascon, Ricardo E. ^{[2
]}

Colston, M. Joseph ^{[2
]}

Hailes, Helen C. ^{[1
]}

机构：

[1] UCL, Dept Chem, London WC1H 0AJ, England

[2] Natl Inst Med Res, London NW7 1AA, England

[3] Univ Exeter, Hatherly Labs, Sch Biosci, Exeter EX4 4PS, Devon, England

[4] GlaxoSmithKline Inc, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON | 2011年 / 67卷 / 02期

基金：

英国生物技术与生命科学研究理事会;

关键词：

Calixarenes; Tuberculosis; Anti-mycobacterial; p-Phenylcalixarene; Calixarene alkylation; Pegylation; POLYOXYETHYLENE ETHERS; TRANSFECTION; CONFORMATION; MACROPHAGES;

D O I：

10.1016/j.tet.2010.11.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of large-ringed calix[6,7,8]arene analogues have been synthesised and their affect against Mycobacterium tuberculosis in vivo established. In general, when p-phenylcalixarenes and tert-butylcalixarenes were not functionalised at the lower rim, low biological activities were observed. However on going from partially to fully lower rim pegylated calixarenes the anti-mycobacterial properties improved. The addition of cyanopropoxy groups at the lower rim gave rise to low activities, whereas the addition of acetate moieties interestingly had pro-TB effects. Two upper rim sulfonated calixarenes showed promising properties. In the course of this work, a high yielding procedure to synthesise p-phenylcalix[7]arene was also established. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：373 / 382

页数：10

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