1,4-二氧喹醛酸酯合成及抑菌活性研究
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摘要
为了合成两种具有抑菌活性的1,4-二氧喹醛酸酯,即1,4-二氧喹喔啉-3-甲基-2-甲酸苯酯和1,4-二氧喹喔啉-3-甲基-2-甲酸肉桂酯,以苯并呋咱为原料,经Beirut反应、酯交换反应,合成了两种喹醛酸酯;1,4-二氧喹喔啉-3-甲基-2-甲酸苯酯合成产率为29.3%,1,4-二氧喹喔啉-3-甲基-2-甲酸肉桂酯合成产率为18.3%。两种1,4-二氧喹醛酸酯对大肠杆菌、金葡萄球菌、青霉菌和枯草杆菌均有明显的抑菌活性。通过测定产物的熔点和光谱分析证明系为所合成的目标产物。
Using benzofuroxan as raw material,two kinds of 1,4- dioxide quinoline aldehydes esters,1,4-dioxide quinoline- 3- methyl- 2- phenyl formate and 1,4- dioxide quinoline- 3- methyl- 2-cinnamylformate,were synthesized by Beirut reaction and ester exchange reaction. The yield of 1,4- dioxide quinoline- 3- methyl- 2- phenyl formate was 29. 3% and the yield of 1,4- dioxide quinoline- 3- methyl- 2- cinnamylformate was 18. 3%. Two kinds of 1,4- dioxide quinoline aldehyde ester have obvious antibacterial activity to Escherichia coli,Staphylococcus aureus,Penicillium sp. and Bacillus subtilis. It was proved that new compounds synthesized in experiment were target compounds by measuring the melting point and spectral analysis.
Using benzofuroxan as raw material,two kinds of 1,4- dioxide quinoline aldehydes esters,1,4-dioxide quinoline- 3- methyl- 2- phenyl formate and 1,4- dioxide quinoline- 3- methyl- 2-cinnamylformate,were synthesized by Beirut reaction and ester exchange reaction. The yield of 1,4- dioxide quinoline- 3- methyl- 2- phenyl formate was 29. 3% and the yield of 1,4- dioxide quinoline- 3- methyl- 2- cinnamylformate was 18. 3%. Two kinds of 1,4- dioxide quinoline aldehyde ester have obvious antibacterial activity to Escherichia coli,Staphylococcus aureus,Penicillium sp. and Bacillus subtilis. It was proved that new compounds synthesized in experiment were target compounds by measuring the melting point and spectral analysis.
引文
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[6]张道凌,梁剑平,刘宇,等.喹喔啉1,4-二氧化物的合成及抗菌活性[J].中国医药工业杂志,2008,39(6):410-412.
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[10]王道坤.国家一类新兽药——喹烯酮[J].畜牧市场,2007,12(1):57-57.
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[12]朱柱振,陈杖榴,冯淇辉.喹乙醇在鸡体内的药物动力学及组织浓度研究[J].畜牧兽医学报,1993(3):258-264.
[13]曾英华,方热军.喹烯酮的研究及应用概况[J].湖南饲料,2010(6):19-20.
[14]王旭,程古月,周秋格,等.兽用喹噁啉类毒理学研究进展[J].中国农学通报,2015(17):16-21.
[15]戴述诚,郭忠东,易惠文.喹烯酮合成方法的改进[J].中国兽药杂志,2005,39(10):42-43.
[16]唐树和,唐树民,孙松华.喹烯酮合成工艺的改进[J].化学通报:印刷版,2009,72(4):381-383.
[17]赵晓丽,郑国钧.喹烯酮合成方法的研究[J].兽药与饲料添加剂,2008,13(3):4-5.
[18]叶孟兆,谢荣春,徐伟亮.2-乙酰基-3-甲基喹喔啉-1,4-二氧化物的合成[J].浙江大学学报:农业与生命科学版,1994(4):427-430.
[19]魏晓然,王琳,罗星,等.3-甲基-2-[3-(2-呋喃基)丙烯甲酰]-喹喔啉-1,4-二氮氧化物合成研究[J].中国兽药杂志,2015,49(6):17-22.
[2]Beutin L,Preller E,Kowalski B.Mutagenicity of quindoxin,its metabolites,and two substituted quinoxaline-di-N-oxides.[J].Antimicrobial Agents&Chemotherapy,1981,20(3):336-343.
[3]Ganley B,Chowdhury G,Bhansali J,et al.Redox-activated,hypoxia-selective DNA cleavage by quinoxaline 1,4-di-Noxide.[J].Bioorganic&Medicinal Chemistry,2001,9(9):2395-2401.
[4]Carta A,Sanna P,Gherardini L,et al.Novel functionalized pyrido[2,3-g]quinoxalinones as antibacterial,antifungal and anticancer agents[J].Farmaco,2001,56(12):933–938.
[5]孔新刚.新1,4-二氧喹喔啉衍生物的合成、抑菌活性及与血清白蛋白相互作用的研究[D].新疆农业大学,2008.
[6]张道凌,梁剑平,刘宇,等.喹喔啉1,4-二氧化物的合成及抗菌活性[J].中国医药工业杂志,2008,39(6):410-412.
[7]马敬中,占升卫,胡超男,等.1,4-二氧喹喔啉甲醛亚胺的合成和抑菌活性[J].应用化学,2006,23(6):637-640.
[8]孔新刚,郭明,毛胜凤,等.新化合物1,4-二氧喹喔啉-3-甲醛缩氨基硫脲-2-甲酸乙酯的合成及抑菌活性[J].浙江农林大学学报,2008,25(6):685-688.
[9]Yen J T,Nienaber J A,Pond W G,et al.Effect of carbadox on growth,fasting metabolism,thyroid function and gastrointestinal tract in young pigs.[J].Journal of Nutrition,1985,115(8):970-979.
[10]王道坤.国家一类新兽药——喹烯酮[J].畜牧市场,2007,12(1):57-57.
[11]Ferrando R,Truhaut R,Raynaud J P,et al.Toxicity by relay.III.Safety for the human consumer of the use of Carbadox,a feed additive for swine,as estimated by a 7 years relay toxicity on dogs[J].Toxicology,1978,11(2):167-183.
[12]朱柱振,陈杖榴,冯淇辉.喹乙醇在鸡体内的药物动力学及组织浓度研究[J].畜牧兽医学报,1993(3):258-264.
[13]曾英华,方热军.喹烯酮的研究及应用概况[J].湖南饲料,2010(6):19-20.
[14]王旭,程古月,周秋格,等.兽用喹噁啉类毒理学研究进展[J].中国农学通报,2015(17):16-21.
[15]戴述诚,郭忠东,易惠文.喹烯酮合成方法的改进[J].中国兽药杂志,2005,39(10):42-43.
[16]唐树和,唐树民,孙松华.喹烯酮合成工艺的改进[J].化学通报:印刷版,2009,72(4):381-383.
[17]赵晓丽,郑国钧.喹烯酮合成方法的研究[J].兽药与饲料添加剂,2008,13(3):4-5.
[18]叶孟兆,谢荣春,徐伟亮.2-乙酰基-3-甲基喹喔啉-1,4-二氧化物的合成[J].浙江大学学报:农业与生命科学版,1994(4):427-430.
[19]魏晓然,王琳,罗星,等.3-甲基-2-[3-(2-呋喃基)丙烯甲酰]-喹喔啉-1,4-二氮氧化物合成研究[J].中国兽药杂志,2015,49(6):17-22.