3-甲基-2-乙酰苯腙喹喔啉1,4-二氧物的合成与抑菌活性研究
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摘要
为了合成一种有抑菌活性的新喹喔啉衍生物,即3-甲基-2-乙酰苯腙喹喔啉1,4-二氧物,以邻硝基苯胺为基本原料,经氧化反应,Beirut反应和加成缩合反应,制得目标产物,产率73.5%。用红外光谱法(IR)、质谱法(MS)和核磁共振谱法(NMR)对产物结构进行表征,证明合成产物为目标产物。并通过抑菌测试发现,新化合物对大肠杆菌、枯草杆菌、金葡萄球菌和青霉菌均有明显的抑菌活性,为今后开展喹喔啉及其衍生物的抗菌药用研究奠定基础。
In order to synthesize a new quinoxaline derivative with antibacterial activity,3-methyl-2-acetyl phenylhydrazone quinoxaline 1,4-dioxygen,using o-nitroaniline as raw material,and aquire the target derivatives in a yield of 73. 5% though Oxidation reaction、Beirut reaction and addition condensation reaction. It was proved that the new compound synthesized in experiment were target compound by infrared spectroscopy( IR),mass spectrometry( MS) and nuclear magnetic resonance spectroscopy( NMR). The antibacterial results showed that the 3-methyl-2-acetyl phenylhydrazone quinoxaline 1,4-dioxane had obvious inhibitory activity against Escherichia coli,Bacillus subtilis,Staphylococcus aureus and Penicillium. The experimental results will lay the foundation for the future research of quinoxaline and its derivatives.
In order to synthesize a new quinoxaline derivative with antibacterial activity,3-methyl-2-acetyl phenylhydrazone quinoxaline 1,4-dioxygen,using o-nitroaniline as raw material,and aquire the target derivatives in a yield of 73. 5% though Oxidation reaction、Beirut reaction and addition condensation reaction. It was proved that the new compound synthesized in experiment were target compound by infrared spectroscopy( IR),mass spectrometry( MS) and nuclear magnetic resonance spectroscopy( NMR). The antibacterial results showed that the 3-methyl-2-acetyl phenylhydrazone quinoxaline 1,4-dioxane had obvious inhibitory activity against Escherichia coli,Bacillus subtilis,Staphylococcus aureus and Penicillium. The experimental results will lay the foundation for the future research of quinoxaline and its derivatives.
引文
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[2]吴玉杰,陈冬梅,陶燕飞,等.高效液相色谱法测定动物组织中3-甲基喹喔啉-2-羧酸残留量[J].分析科学学报,2009,25(4):427-430.
[3]张春玲,许秀枝,王艰,等.3-取代喹喔啉衍生物的合成及其抗肿瘤活性的研究[J].广东药学院学报,2013,29(1):25-28.
[4]Xun L I,Yang K H,Xian-Jun Q U,et al.Advances in the research of quinoxalinonederivatives[J].Chinese Journal of Medicinal Chemistry,2006,31(11):979-989.
[5]Villalobos-Rocha J C,Sánchez-Torres L,Nogueda-Torres B,et al.Anti-Trypanosomacruzi and anti-leishmanial activity by quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives[J].Parasitology Research,2014,113(6):2027-2035.
[6]李建立,万玉春,王艳菊,等.新型喹喔啉衍生物的合成、光物理性质及理论分析[J].发光学报,2011,32(10):1024-1029.
[7]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.
[8]刘宇芳,刘博,董振明,等.苯并呋咱的新法合成[J].山西大学学报(自然科学版),2010,33(2):244-246.
[9]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.
[10]马敬中,王洪波,江洪.1,4-二氧喹喔啉-2-甲醛酰腙的合成和除草活性研究[J].精细化工,2004,21(4):309-312.
[11]马敬中,胡超男,占升卫,等.1,4-二氧喹喔啉甲醛双腙的合成及除草活性研究[J].现代化工,2005,25(6):27-28.
[12]李荀,杨康辉,曲显俊,等.喹喔啉类化合物的生物活性研究进展[J].药学研究,2007,26(1):34-36.
[13]Jaso A,Zarranz B,Aldana I,et al.Synthesis of new quinoxaline-2-carboxylate 1,4-dioxide derivatives as anti-Mycobacterium tuberculosis agents.[J].Journal of Medicinal Chemistry,2005,48(6):2019-25.
[14]Dudash J,Zhang Y,Moore J B,et al.Synthesis and evaluation of3-anilino-quinoxalinones as glycogen phosphorylase inhibitors[J].Bioorganic&Medicinal Chemistry Letters,2005,15(21):4790-4793.