具类辣素结构丙烯酰胺的合成及其抑菌和防污性能

doi:10.3724/SP.J.1095.2014.30466

摘要/Abstract

摘要： 以N-羟甲基丙烯酰胺和苯酚类化合物为原料，合成了N-(2-羟基-3-丙烯酰胺甲基-4,6-二甲基苄基)丙烯酰胺(HMABA)、N-(2-羟基-3-丙烯酰胺甲基-4,5-二甲基苄基)丙烯酰胺(AMHBA)、N-(3,5-二甲基-4-羟基苄基)丙烯酰胺(MHBA)、N-(3,6-二甲基-4-丙烯酰胺甲基-2-羟基苄基)丙烯酰胺(MAHBA)和N-(2甲氧基-4-甲基-5-丙烯酰胺甲基苄基)丙烯酰胺(MMABA)5个类辣素结构的丙烯酰胺衍生物。通过红外光谱（IR）、核磁波谱（1H NMR）、质谱（HR-MS）和元素分析对化合物的结构进行了表征。抑菌试验表明，HMABA对金黄色葡萄球菌和大肠杆菌的抑制效果最好，最低抑菌浓度均可达0.125 g/L。将此5个化合物作为防污剂制备海洋防污涂料，120 d的实海结果表明，基本无污损海生物附着。

关键词: 含类辣素结构的丙烯酰胺, 合成, 抑菌, 防污性能

Abstract: Five acrylamide compounds containing capsaicin moieties were synthesized. Their structures were confirmed by IR spectroscopy, 1H NMR spectroscopy, HRMS and elemental analysis. The results of bacterium-inhibition experiments concluded that the minimal inhibitory concentration(MIC) of five tag compounds respectively to Staphyloccocus aureus and Escherichia coli both were 0.125 g/L. The antifouling properties of coatings were examined by immersing test panels in the sea for more than 120 days. The result shows that the test panels are covered with a few macroscopic fouling organisms balanus.

Key words: acrylamide containing capsaicin derivative, synthesis, bacterium-inhibition, antifoulant properties

中图分类号:

O625

于晓琳, 于良民, 姜晓辉. 具类辣素结构丙烯酰胺的合成及其抑菌和防污性能[J]. 应用化学, DOI: 10.3724/SP.J.1095.2014.30466.

YU Xiaolin,YU Liangmin*, JIANG Xiaohui. Synthesis, Bacteriostasic Activity and Antifouling Capability of Acrylamide Containing Capsaicin Derivative[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30466.

参考文献

[1] Bauer R S. Epoxy Resin,ACS Symposium Series[M]. Washington DC:American Chemical Society,1985:931-961.

[2] QIAN Junmin,LI Xuxiang. Modification of Epoxy Resin[J]. Eng. Plastics Appl.,2001,29(10):50-53(in Chinese).

钱军民，李旭祥. 环氧树脂改性研究进展[J]. 工程塑料应用,2001,29(10):50-53.

[3] ZHAO Zhichao,YUAN Caideng,XU Tao,et al. Environmentally Friendly Epoxy Coating[J]. Thermoset Resin,2005,20(6):32-35(in Chinese).

赵志超，袁才登，徐涛，等. 环保型环氧树脂涂料[J]. 热固性树脂,2005,20(6):32-35.

[4] Takahirookamatsu,Mitsukazuochi. Effect on the Toughness and Adhesion Properties of Epoxy Resin Modified with Silylcrosslinked Urethane Microsphere[J]. Polymer,2002,43(3):721-730.

[5] CONG Weiwei,YU Liangmin,ZHAO Haizhou,et al. N,N′-Dibutyl Dithio Oxymethyl Acrylamide, Antibacterial and Antifouling Properties[J]. Paint Ind,2010,9(40):9-15(in Chinese).

丛巍巍，于良民，赵海洲，等. N,N′-二丁氧基甲基二硫代二丙烯酰胺的合成、抑菌和防污性能研究[J]. 涂料工业,2010,9(40):9-15.

[6] Oommen S,John A R,Stinivas G,et al.Allicin(from garlic) Induces Caspase-mediated Apoptosis in Cancer Cells[J]. Physiol Mol Plant Pathol,2004,65(2):79.

[7] JIN Yong,LI Jun,YAO Hongwei,et al.Pepper Extract Inflammatory and Analgesic Effects[J]. Anhui Med Univ,2001,36(6)：430-431(in Chinese).

金涌，李俊，姚宏伟，等. 辣椒提取物的抗炎镇痛作用［J］. 安徽医药大学学报，2001，36(6)：430-431.

[8] Kenneth J Fischer. Marine Organism Repellent Covering for Protection of Underwater Objects and Method of Applying Same:US,5226380[P],1993.

[9] James L Watts. Antifouling Coating Composition Containing Capsaicin:US,5397385[P],1995.

[10] Hamanok,Nagatak. Naimal Repelling Aqueous Coating Composition:JP,6219906[P],1994.

[11] Wang J L,Peng Z H,Zhou S Z,et al. A Study of Pungency of Capsaicinoid as Affectd by Their Molecular Structure Alteration[J]. Sci Res,2011,2:109-115.

[12] PENG Bixian,WANG Junlian,PENG Zhenghong,et al. Synthetic Capsaicin Homologues, Spiciness and Antifouling Properties of Marine Organisms[J]. Sci China:Chem,2011,41(10):1464-1654(in Chinese)

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):1464-1654.

[13] XU Huanzhi,YU Liangmin,ZHANG Zhiming,et al. A Side-chain Hanging Pepper Rings Acrylamide Resin and Its Preparation Method and Application:CN,1624017[P],2005-6-8(in Chinese).

徐焕志,于良民,张志明,等. 一种侧链悬挂胡椒环的丙烯酰胺树脂及其制备方法和应用:CN,1624017A[P],2005-6-8.

[14] CHEN Sihao,XU Zicheng,XU Jingli,et al.Synthesis of Capsaicin:CN,1982287A[P],2007(in Chinese).

陈思浩，徐子成，徐菁利，等. 辣素的合成方法:CN,1982287A[P],2007.

[15] MurainaI 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] GB/T 5370-85,Antifouling Panels in Shallow Submergence[S].

[17] XU Huanzhi,YU Liangmin,LI Changcheng,et al. Capsaicin Derivatives and Their Inhibitory Activity Closterium[J]. Chinese J Appl Chem,2007,24(8):911-916(in Chinese).

徐焕志,于良民,李昌诚,等. 辣素衍生物的合成及其对新月菱形藻的抑制活性[J]. 应用化学,2007,24(8): 911-916.

[18] Pernak A,Skrzypczak A. 3-Alkylthiomethyl-1-ethylimidazolium Chlorides Correlation between Critical Micelle Concentrations and Minimum Inhibitory Concentrations[J]. Eur J Med Chem,1996,31(11):901-903.