Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones

被引：7
作者：
Bianchi, DA
Sutich, EG
Kaufman, TS
机构：
[1] Univ Nacl Rosario, Inst Quim Organ Sintesis, CONICET, UNR,Fac Ciencias Bioquim & Farmaceut, Rosario, Argentina
[2] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Dept Microbiol, Rosario, Argentina
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 03期
关键词：
D O I：
10.1016/j.bmcl.2003.11.015
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The elaboration and biological activity of 15, containing the proposed pharmacophore for the antibiotic activity of the pyranonaphthoquinones, are reported. The synthetic strategy involved acid-catalyzed lactonization of mandelate 17 for isochroman ring formation, in combination with a Wittig-oxa-Michael functionalization of isochroman-3-ol derivative 20, a lactonization involving configurational inversion of a benzylic alcohol and a final AgO oxidation. Compound 15 showed activity against Staphylococcus aureus and Bacillus subtilis with MIC of 64 and 32 mug/mL, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
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页码：757 / 760
页数：4
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