CAJ | 학술논문

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(Phytphythra capsici)抑制率达58.5%,化合物7c对番茄灰霉病菌(Botrytis cinema)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%.
2-갑기간이분혹5-갑기간이분분별여dl-평과산혹을선을산을지,재농류산최화하,경Peachmann축합반응득도산형동(7-간기향두소)유사물5～7.5～7경갑기화득신화합물5a,6a화7a;경Williamson반응,TBAB(사정정기추화안)상전이최화합성료14개신적향두소류화합물5b～5e,6b～6f,7b～7f.경IR,MS,~1H NMR급원소분석대소유화합물적결구진행료표정.초보생물활성실험결과표명,재50 μg/mL농도하,화합물6대랄초역매병균(Phytphythra capsici)억제솔체58.5%,화합물7c대번가회매병균(Botrytis cinema)억제솔위54.0%.화합물6c대수도문고병균(Rhizoctonia solani)적억제솔체83.7%.
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.