Synthesis and antimycobacterial activity of agelasine E and analogs

被引：69

作者：

Bakkestuen, AK ^{[1
]}

Gundersen, LL ^{[1
]}

Petersen, D ^{[1
]}

Utenova, BT ^{[1
]}

Vik, A ^{[1
]}

机构：

[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 06期

关键词：

D O I：

10.1039/b417471b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Agelasine E, previously isolated from the marine sponge Agelas nakamurai, has been synthesized for the. first time, together with analogs with various terpenoid side chains. Treatment of N-6- methoxy- 9- methyl- 9H- purin- 6- amine with allylic bromides gave the desired 7,9- dialkylpurinium salts together with minor amounts of the N6- alkylated isomer. The N6- methoxy group was finally removed reductively. H-1 - (NHMBC)-N-15 and H-1 - N-15 HSQC NMR spectroscopy gave additional information on tautomerism and charge delocalization in the purine derivatives studied. The heterocyclic products were screened for activity against Mycobacterium tuberculosis and agelasine analogs carrying a relatively long terpenoid substituent in the purine 7- position and a methoxy group at N- 6 were potent inhibitors of bacterial growth. Since agelasine analogs with the geranylgeranyl chain at N- 7 exhibited antimicrobial activity, several strategies for synthesis of geometrically pure ( 2E, 6E, 10E)- geranylgeranyl bromide from geranyllinalool were evaluated.

引用

页码：1025 / 1033

页数：9

共 28 条

[11] The 11 positional isomers of Nx,Ny-dimethyladenine:: Their chemistry, physicochemical properties, and biological activities [J].