噻吩并嘧啶酮衍生物的合成及其抑菌活性  

Synthesis and bacteriostatic activities of thienopyrimidinones

作　　者：胡海军[1] 严凯[1] 陈鸿[1] 廖全斌[1] 刘明国[1] 

机构地区：[1]三峡大学化学与生命科学学院,湖北宜昌443002

出　　处：《化学研究与应用》2012年第1期31-36,共6页Chemical Research and Application

基　　金：天然产物研究与利用湖北省重点实验室开放研究基金项目(批准号:2006NP01);三峡大学自然科学研究基金项目(HY0803)资助

摘　　要：利用三组分氮杂Wittig反应,以磷亚胺2、对氯苯基异氰酸酯和酚,合成了16个未见文献报道的2-芳氧基-3-对氯苯基-3,5,6,7-四氢-4H-环戊二烯并[4,5]噻吩并[2,3-d]-嘧啶-4-酮衍生物,产率52～74%。通过IR、1H NMR、MS和元素分析对目标化合物的结构进行了表征。初步探讨了所合成化合物的抑菌活性,结果显示所合成的化合物对真菌的抑制活性优于对细菌的抑制活性,对桔青霉菌的抑制活性在65.2%以上,其中5n的抑菌率最高,达到89.1%。在化合物对细菌的抑制活性中,对绿脓杆菌的抑菌率较好,在52.8～73.0%之间,对金黄色葡萄球菌的抑制活性最低,在43.3～65.5%之间。Sixteen new 2-aryloxy-3-（4-chluorophenyl ） -3,5,6,7-tetrahydro-4H-cyclopenta [ 4,5 ] thieno [ 2,3-d ] pyrimidin-4-ones were synthesized in 52 - 74% yields by aza-Wittig reaction of iminophosphorane 2 with 4-chluorophenyl iso-cyanate, and subsequent reaction with phenols. The structures were confirmed by IR, ^1H NMR, MS and element analyse. Initial activity evaluation of the title compounds indicated their antifungal activities were better than anti-bacterial activities. The inhibitory activities against Penicillium citrinum Thorn were higher than 65.2%, of which 5n exhibited best inhibition rate of 89. 1%. Their anti-bacterial inhibition rate against Pseudomonas acruginosa were 52. 8 -73.0% ,which were better than Staphylococcus aureus with the lowest inhibition rate of 43.3 -65.5%.

关 键 词：四氢环戊二烯并噻吩并嘧啶酮 氮杂WITTIG反应 合成 抑菌活性 

分 类 号：O626.41[理学—有机化学]