姜晓辉,潘永萍,丛巍巍,于良民

• 1:中国海洋大学海洋化学理论与工程技术教育部重点实验室

摘要(Abstract)：

以N-羟甲基苯甲酰胺和取代芳烃为原料,合成了N-(3-苯甲酰胺甲基-2-羟基-4,5-二甲基苄基)苯甲酰胺(A)、N-(3-苯甲酰胺甲基-2-羟基-4,6-二甲基苄基)苯甲酰胺(B)、N-(4-苯甲酰胺甲基-2-羟基-3,6-二甲基苄基)苯甲酰胺(C)、N-(3-甲基-5-苯甲酰胺甲基-2-羟基苄基)苯甲酰胺(D)、N-(4-甲基-5-苯甲酰胺甲基-2-羟基苄基)苯甲酰胺(E)、N-(5-苯甲酰胺甲基-2-羟基-3-甲氧基苄基)苯甲酰胺(F)和N-(5-苯甲酰胺甲基-2-甲氧基-4-甲基苄基)苯甲酰胺(G)共7种双苯甲酰胺基取代的类辣素结构化合物。通过红外光谱(IR)和核磁氢谱(1 H NMR)对其结构进行了表征。抑菌试验结果表明化合物F和化合物G对2种受试菌金黄色葡萄球菌和大肠杆菌的抑制活性最高,最小抑菌浓度均可达到0.125mg/mL。以该7种化合物为辅助防污剂,复合氧化亚铜制备海洋防污涂料,实海挂板120天后,除含D试片外其余6个试片均表面光洁无污损生物附着,表现出优良的防污性能。

关键词(KeyWords)： 类辣素结构;双苯甲酰胺;合成;抑菌活性;防污活性

Abstract:

Keywords:

基金项目(Foundation): 中央高校基本科研业务费专项资金项目(201562026,201413024);; 国家科技支撑计划项目(2012BAB15B02);; 高等学校博士学科点专项科研基金项目(20130132130001)资助~~

作者(Author): 姜晓辉,潘永萍,丛巍巍,于良民

DOI: 10.16441/j.cnki.hdxb.20160296

参考文献(References)：

• [1]Callow M E,Callow J A.Marine biofouling:a sticky problem[J].Biologist,2002,49(1):1-5.
• [2]Schultz M P,Bendick J A,Holm E R,et al.Economic impact of biofouling on a naval surface ship[J].Biofouling,2011,27(1):87-98.
• [3]Abarzua S,Jakubowski S.Biotechnological investigation for the prevention of biofouling:Biological and biochemical principles for the preventionof biofouling[J].Marine Ecology Progress Series,1995,123(1):301-312.
• [4]Davis A R,Targett N M,Mcconnell O J,et al.Epibiosis of marine algae and benthic invertebrates:natural products chemistry and other mechanisms inhibiting settlement and overgrowth[J].Bioorganic Marine Chemistry,1989,3:85-114.
• [5]Finnie A A,Williams D N.Paint and coatings technology for the control of marine fouling[J].Oxford:Wiley-Blackwell,2010,12(12):185-206.
• [6]Guo S F,Lee H P,Chaw K C,et al.Effect of ultrasound on cyprids and juvenile barnacles[J].Biofouling,2011,27(2):185-192.
• [7]Guo S F,Lee H P,Teo S L,et al.Inhibition of barnacle cyprid settlement using low frequency and intensity ultrasound[J].Biofouling,2012,28(2):131-141.
• [8]J Bellas J.Prediction and assessment of mixture toxicity of compounds in antifouling paints using the sea-urchin embryo-larval bioassay[J].Aquatic Toxicology,2008,88(4):308-315.
• [9]彭必先,王俊莲,彭争宏,等.辣椒素同系物合成、辣度及海洋生物防污性能研究[J].中国科学:化学,2011,41(10):1646-1654.Peng B X,Wang J L,Peng Z H,et al.Studies on the synthesis,pungency and anti-biofouling performance of capsaicin analogues[J].Scientia Sinica Chimica,2011,41(10):1646-1654.
• [10]金涌,李俊,姚宏伟,等.辣椒提取物的抗炎镇痛作用[J].安徽医科大学学报,2001,36(6):430-431.Jin Y,Li J,Yao H W,et al.Antiinflammatory and analgesic effects of extract of capsicum[J].Acta Universitatis Medicinalis Anhui,2001,36(6):430-431.
• [11]唐胜球,董小英.辣椒素的生理功能及应用前景[J].粮油食品科技,2002,10(6):25-27.Tang S Q,Dong X Y.Physiological function and application prospect of capsaicin[J].Science and Technology of Cereals,Oils and Foods,2002,10(6):25-27.
• [12]汪文龙,黄燕兰,胡惟孝,等.辣椒素类似物的合成、结构及抗肿瘤活性[J].高等学校化学学报,2010,31(12):2400-2406.Wang W L,Huang Y L,Hu W X,et al.Synthesis,structures and anti-tumor properties of capsaicin analogues[J].Chemical Journal of Chinese Universities,2010,31(12):2400-2406.
• [13]Wang J L,Peng Z H,Zhou S Z,et al.A study of pungency of capsaicinoid as affected by their molecular structure alteration[J].Pharmacology&Pharmacy,2011,2:109-115.
• [14]Callow M E,Fletcher R L.The influence of low surface energy materials on bioadhesion——a review[J].International Biodeterioration&Biodegradation,1994,34(3-4):333-348.
• [15]Muraina I A,Picard J,Eloff J N.Development of a reproducible method to determine minimum inhibitory concentration(MIC)of plant extract against a slow-growing mycoplasmas organism[J].Phytomedicine,2009,16(2):262-264.
• [16]于良民,王宝娟,李霞.新型吲哚类防污剂抑菌性能评价[J].涂料工业,2007,37(4):17-20.Yu L M,Wang B J,Li X.Evaluation of antibacterial activity of indole derivatives as antifouling agent[J].Paint&Coatings Industry,2007,37(4):17-20.
• [17]王宝娟.海洋防污涂料及其主要成分的生物学性能研究[D].青岛:中国海洋大学,2007.Wang B J.Study on Capability of Marine Antifouling Paints and Its Main Compontent[D].Qingdao:Ocean University of China,2007.
• [18]董磊.羧甲基壳聚糖金属盐/壳聚糖包覆氧化亚铜的制备及其海洋防污性能研究[D].青岛:中国海洋大学,2007.Dong L.The Preparation of Carboxymethyl Chitosan Salt/nano Cu2O Enclosed by Chitosan and the Study of Their Usage in Marine Antifouling Paint[D].Qingdao:Ocean University of China,2007.
• [19]Pernak J,Skrzypczak A.3-alkylthiomethyl-1-ethylimidazolium chlorides correlation between critical micelle concentrations and minimum inhibitory concentrations[J].European Journal of Medicinal Chemistry,1996,31(11):901-903.
• [20]防污漆样板浅海浸泡试验方法[S].GB/T 5370-2007.Method for testing antifouling panels in shallow submergence[S].GB/T 5370-2007.
• [21]袁帅,刘峥,赖丽燕,等.含羧基席夫碱抑菌活性定量构效关系研究[J].化学通报,2013,76(12):1126-1131.Yuan S,Liu Z,Lai L Y.Study on quantitative structure-activity relationship of antibacterial activities of schiff bases containing carboxyl[J].Chemistry Bulletin,2013,76(12):1126-1131.

文章评论(Comment)：