伞型酮类似物的合成及抗菌作用

2-甲基间二酚或5-甲基间二酚分别与dl-苹果酸或乙酰乙酸乙酯, 在浓硫酸催化下, 经Peachmann缩合反应得到伞型酮(7-羟基香豆素)类似物5～7. 5～7经甲基化得新化合物5a, 6a和7a; 经Williamson反应, TBAB(四正丁基溴化铵)相转移催化合成了14个新的香豆素类化合物5b～5e, 6b～6f, 7b～7f. 经IR, MS, ¹H NMR及元素分析对所有化合物的结构进行了表征. 初步生物活性实验结果表明, 在50 μg/mL浓度下, 化合物6对辣椒疫霉病菌(Phytophythora capsici)抑制率达58.5%, 化合物7c对番茄灰霉病菌(Botrytis cinerea)抑制率为54.0%, 化合物6c对水稻纹枯病菌(Rhizoctonia solani)的抑制率达83.7%.

Synthesis and Antifungal Activities of Umbelliferone Analogs

Resorcinol was reacted with dl-malic acid or ethyl acetoacetate under the catalysis of sulfuric acid via Pechmann condensation to produce three umbelliferone (7-hydroxycoumarin) analogs 5～7. 5a, 6a and 7a were synthesized by methylation of 5～7. Fourteen new coumarin compounds 5b～5e, 6b～6f and 7b～7f were prepared from the intermediates and alkyl halides via Williamson reaction using TBAB (tetrabutylammonium bromide) as catalyst. The structures of all those new compounds were confirmed by ~1H NMR, IR, MS techniques and elemental analysis. The preliminary bioassay showed that, compound 6 had inhibitory activity 58.5% against Phytophythora capsici, 7c had antifungal activity 54.0% against Botry-tis cinerea and 6c had antifungal activity 83.7.0% against Rhizoctonia solani at 50 μg/mL.