3,3-二甲基-1-(吡啶-3-基)-丁-2-酮肟酯的合成及抑菌活性
收稿日期: 2017-05-05
修回日期: 2017-06-01
网络出版日期: 2017-06-16
基金资助
山东省自然科学基金（No.ZR2014BM030）资助项目.
Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity
Received date: 2017-05-05
Revised date: 2017-06-01
Online published: 2017-06-16
Supported by
Project supported by the Natural Science Foundation of Shandong Province (No.ZR2014BM030).
以3-甲基吡啶、特戊酸乙酯、盐酸羟胺和取代苯甲酸等为原料，经加成、肟化和酯化反应，合成了12种新型的3，3-二甲基（吡啶-3-基）-丁-2-酮肟酯.该方法反应条件比较温和、收率高.化合物的结构通过IR、1H NMR、13C NMR和元素分析确证.采用菌丝生长速率法测试了目标化合物对两种病原菌的离体抑制活性，O-（4-溴苯甲酰基）-3，3-二甲基-1-（吡啶-3-基）-丁-2-酮肟（3h）和O-（4-氯苯甲酰基）-3，3-二甲基-1-（吡啶-3-基）-丁-2-酮肟（3j）对菌核菌有较强的抑制活性，EC50值分别为5.07和4.81 μg/mL；3h、3j和O-（3，4-二氯苯甲酰基）-3，3-二甲基-1-（吡啶-3-基）-丁-2-酮肟（3l）对灰霉菌显示出较高的抑制活性，EC50值分别为4.98、5.44和6.34 μg/mL.
昝宁宁 , 张钰镭 , 张帅 , 刘思 , 姜林 . 3,3-二甲基-1-(吡啶-3-基)-丁-2-酮肟酯的合成及抑菌活性[J]. 有机化学, 2017 , 37(10) : 2767 -2771 . DOI: 10.6023/cjoc201705009
A series of novel pyridine derivatives containing oxime esters have been synthesized from 3-methylpyridine, ethyl pivalate, hydroxylamine hydrochloride and substituted benzoic acid by addition, oximization and esterification reactions,which has the advantages of moderate reaction condition and high yield. Their structures were elucidated by IR, 1H NMR, 13C NMR and elemental analysis. Moreover, the target compounds were evaluated for their antifungal activity against two plant pathogens by the mycelium growth rate method. The results indicated that O-(4-bromobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3h) and O-(4-chlorobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3j) exhibited strong antifungal activity against S. sclerotiorum with EC50 values of 5.07 and 4.81 μg/mL, and 3h, 3j and O-(3,4-dichlorobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3l) displayed high antifungal activity against B. cinerea with EC50 values of 4.98, 5.44 and 6.34 μg/mL, respectively.
Key words： pyridine; ketones; oxime; carboxylic acids; synthesis design; antifungal activity
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