与蠕孢菌素相关的氧杂双环类似物的合成及其植物生长特性

Synthesis and phytogrowth properties of oxabicyclic analogues related to helminthosporin.

作者信息

Barbosa Luiz Cláudio Almeida, Nogueira Leonardo Brandão, Maltha Célia Regina Alvares, Teixeira Róbson Ricardo, Silva Antônio Alberto

机构信息

Department of Chemistry, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil.

出版信息

Molecules. 2009 Jan 1;14(1):160-73. doi: 10.3390/molecules14010160.

DOI:10.3390/molecules14010160

PMID:19127245

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6253885/

Abstract

This investigation describes the synthesis and biological evaluation of a series of oxabicyclic analogues related to the helminthosporins. Four oxabicycles were prepared by [4+3] cycloaddition of an oxyallyl carbocation, generated in situ from 2,4-dibromopentan-3-one, with selected furans. Functional group manipulations of the oxabicyclic architecture generated nine further derivatives. The phytotoxic properties of these oxabicycles were evaluated as their ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings. In both species, the most active compounds were oxabicycles possessing a carbonyl group conjugated with a double bond.

摘要

本研究描述了一系列与蠕孢菌素相关的氧杂双环类似物的合成及生物学评价。通过由2,4-二溴戊-3-酮原位生成的氧烯丙基碳正离子与选定的呋喃进行[4+3]环加成反应制备了四种氧杂双环。对氧杂双环结构进行官能团操作又得到了另外九种衍生物。评估了这些氧杂双环的植物毒性，即它们干扰高粱和黄瓜幼苗生长的能力。在这两个物种中，活性最高的化合物是具有与双键共轭的羰基的氧杂双环。