Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents
Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents
复制标题
具有2-苯氧基甲基取代基的4H-3,1-苯并恶嗪-4-酮和3H-喹唑啉-4-酮的简易合成及除草评价
DOI：
10.3390/molecules17033181
复制
发表时间：
2012-03-01
期刊：
影响因子：
4.6
通讯作者：
Zhang, Aidong
中科院分区：
文献类型：
--
作者：
Aibibuli, Zumuretiguli;Wang, Yufeng;Zhang, Aidong
通过邻氨基苯甲酸与2-苯氧基乙酰氯的一锅N-酰化/闭环反应，合成了一系列具有苯氧甲基取代基的4H-3，1-苯并恶嗪-4-酮和~3H-喹唑啉-4-酮，并用氨基取代得到了~3H-喹唑啉-4-酮。对模式植物藜草(单子叶植物)和油菜(双子叶植物)进行了除草评价，大多数标题化合物都表现出较高的植物毒性。活性亚结构和抑制表型分析表明，这些化合物可能属于植物激素抑制剂类。几个有代表性的化合物与激素受体TIR1的对接研究发现，这些化合物在活性部位有明显的构象匹配，暗示这些化合物是针对该受体的潜在先导化合物。
Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently substituted with amino derivatives to obtain the 3H-quinazolin-4-ones. The herbicidal evaluation was performed on the model plants barnyard grass (a monocotyledon) and rape (a dicotyledon), and most of the title compounds displayed high levels of phytotoxicity. The active substructure and inhibitory phenotype analysis indicated that these compounds could be attributed to the class of plant hormone inhibitors. A docking study of several representative compounds with the hormone receptor TIR1 revealed an appreciable conformational match in the active site, implicating these compounds are potential lead hits targeting this receptor.