含吗啉基片段的水杨醛席夫碱类化合物的合成及其淬灭1,1-二苯基-2-三硝基苯肼自由基性能
|
摘要
通过3-氟-4-吗啉基苯胺和取代水杨醛缩合反应,合成了14个含吗啉基片段水杨醛席夫碱类化合物(Ⅰa-Ⅰn)。通过核磁共振波谱仪(NMR)、傅里叶变换红外光谱仪(FTIR)、液相色谱-质谱联用仪(LC-MS)和元素分析等技术手段研究了产物的结构和淬灭1,1-二苯基-2-三硝基苯肼(DPPH)自由基的活性。结果表明,在0. 02～0. 10 g/L,所有化合物均表现出一定的淬灭DPPH自由基活性。其中,化合物Ⅰd和Ⅰf表现出较为优异的性能,化合物Ⅰd的活性在30%～55%,化合物Ⅰf的活性则大于50%。随着化合物Ⅰd、Ⅰh、Ⅰj和Ⅰn质量浓度的增大,其淬灭DPPH自由基的活性均呈现增强趋势。
Fourteen kinds of salicylaldehyde Schiff bases containing morpholinyl fragments are synthesized by the condensation reaction of 3-fluoro-4-morpholiniline and substituted salicylate and confirmed by nuclear magnetic resonance spectroscopy(NMR), Fourier transform infrared spectrometer(FTIR), liquid chromatography-mass spectrometer(LC-MS) and element analysis. The 1,1-diphenyl-2-picrylhydrazyl(DPPH) radical quenching activities of these Schiff bases are also studied. The results show that all compounds show certain quenching activity of DPPH radicals at concentrations of 0. 02 to 0. 10 g/L. Among them,the compounds Ⅰd and Ⅰf show excellent properties. The activity of compound Ⅰd is between 30% and55%,and the activity of compoundⅠf is more than 50%. With the increase of the concentration of compoundsⅠd,Ⅰh,Ⅰj andⅠn,the DPPH radical quenching activities increase.
Fourteen kinds of salicylaldehyde Schiff bases containing morpholinyl fragments are synthesized by the condensation reaction of 3-fluoro-4-morpholiniline and substituted salicylate and confirmed by nuclear magnetic resonance spectroscopy(NMR), Fourier transform infrared spectrometer(FTIR), liquid chromatography-mass spectrometer(LC-MS) and element analysis. The 1,1-diphenyl-2-picrylhydrazyl(DPPH) radical quenching activities of these Schiff bases are also studied. The results show that all compounds show certain quenching activity of DPPH radicals at concentrations of 0. 02 to 0. 10 g/L. Among them,the compounds Ⅰd and Ⅰf show excellent properties. The activity of compound Ⅰd is between 30% and55%,and the activity of compoundⅠf is more than 50%. With the increase of the concentration of compoundsⅠd,Ⅰh,Ⅰj andⅠn,the DPPH radical quenching activities increase.
引文
[1]ZHONG Keli,WANG Yutong,YU Qixuan,et al. Progress in Fluorescence Probes Based on 4-(N,N-Diethylamino)Salicylaldehyde Schiff Base[J]. Chem Bull,2018,81(1):37-44(in Chinese).钟克利,王禹童,于奇轩,等.基于4-(N,N-二乙氨基)水杨醛席夫碱类荧光探针的研究进展[J].化学通报,2018,81(1):37-44.
[2]Panneerselvam P,Nair R R,Vijayalakshmi G,et al. Synthesis of Schiff Bases of 4-(4-Aminophenyl)-morpholine as Potential Antimicrobial Agents[J]. Eur J Med Chem,2005,40(2):225-229.
[3]Kumari S,Chauhan G S. New Cellulose-Lysine Schiff-Base-Based Sensor-Adsorbent for Mercury Ions[J]. Appl Mater Interfaces,2014,6(8):5908-5917.
[4]Li C,Liu J C,Li Y R,et al. Synthesis and Antimicrobial Evaluation of 5-Aryl-1,2,4-triazole-3-thione Derivatives Containing a Rhodanine Moiety[J]. Bioorg Med Chem Lett,2015,25(15):3052-3056.
[5]LU Tianqi,WANG Po,RONG Zikun,et al. Synthesis and Optical Property of Schiff Base Containing Triphenylamine Group[J]. Chinese J Synth Chem,2017,25(12):1004-1007(in Chinese).鲁天琪,王坡,荣子鲲,等.一种含三苯胺基团的席夫碱的合成及其光学性[J].合成化学,2017,25(12):1004-1007.
[6]YUAN Zeli,WU Qing,YANG Xingbian,et al. Synthesis and Antibacterial Activity of Novel Schiff Base Macrocyclic Compounds Cotaining Triazole[J]. Chinese J Org Chem,2011,31(10):1698-1702.(in Chinese).袁泽利,吴庆,杨兴变,等.新型含均三唑席夫碱型大环化合物的合成及其抗菌活性[J].有机化学,2011,31(10):1698-1702.
[7]HE Qiangfang,WU Yinghong,CAI Zhijian,et al. Synthesis of Fluorescent Cross-Linked Stabilized Polymeric Micelles Based on Salicylidene Schiff Base/Zn2+Complexes and Sensor for Cu2+Detection[J]. Chinese J Appl Chem,2016,33(6):701-709(in Chinese).何强芳,吴映红,蔡志健,等.基于水杨醛席夫碱锌配合物交联稳定化荧光聚合物胶束的合成及其对铜离子的荧光响应性[J].应用化学,2016,33(6):701-709.
[8]Jin F,Pan C Y,Lu T Q,et al. Syntheses,Crystal Structures,DFT Calculation and Optical Properties of a Schiff Base and Its Dinuclear Mercury(Ⅱ)Complex[J]. Chinese J Struct Chem,2017,36(2):250-257.
[9]CAO Yi,LU Yun. Syntheses and Properties of Three Schiff Bases Containing Salicylaldehyde Units[J]. Chem Bull,2017,80(6):539-543(in Chinese).曹义,陆云.三种水杨醛类席夫碱的合成与性质研究[J].化学通报,2017,80(6):539-543.
[10]Shen Z H,Shi Y X,Yang M Y,et al. Synthesis,Crystal Structure,DFT Studies and Biological Activity of a Novel Schiff Base Containing Triazolo[4,3-a]pyridine Moiety[J]. Chinese J Struct Chem,2016,35(3):457-464.
[11]PAN Dingwu,DU Huan,LV Xinyang,et al. Synthesis and Antibacterial Activities of Novel Quinazoline-2,4-dione Derivatives Containing the 1,2,4-Triazole Schiff-Base Unit[J]. Chinese J Org Chem,2016,36(4):818-825(in Chinese).潘顶伍,杜欢,吕新阳,等.含1,2,4-三唑席夫碱的新型喹唑啉-2,4-二酮类衍生物的合成及其抗细菌活性研究[J].有机化学,2016,36(4):818-825.
[12]LI Yingjun,ZHANG Nan,JIN Kun,et al. Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu2+[J].Chinese J Org Chem,2017,37(10):2640-2646(in Chinese).李英俊,张楠,靳焜,等.新型基于咔唑-氨基硫脲席夫碱识别Cu2+的探针[J].有机化学,2017,37(10):2640-2646.
[13]Gao B J,Zhang D D,Li Y B. Synthesis and Photoluminescence Properties of Novel Schiff Base Type Polymer-Rare Earth Complexes Containing Furfural-Based Bidentate Schiff Base Ligands[J]. Opt Mater,2018,77:77-86.
[14]LIU Junhu,LIU Yong,JIAN Junyou,et al. Synthesis and Fungicidal Activities of Novel Quinazoline Derivatives Containing1,2,4-Triazole Schiff-Base Unit[J]. Chinese J Org Chem,2013,33:370-374(in Chinese).刘军虎,刘勇,蹇军友,等.含1,2,4-三唑席夫碱的新型喹唑啉类化合物的合成及其抗菌活性研究[J].有机化学,2013,33:370-374.
[15]XIE Qingfan,LU Huiqiang,YOU Xingying,et al. Synthesis,Characterization and Antioxidant Effect of Complexes from2-Aminomethyl Pyridine 5-Bromosalicylaldehyde Schiff base[J]. Chem Res,2015,26(1):35-38(in Chinese).解庆范,卢慧强,游兴英,等. 2-氨甲基吡啶缩5-溴水杨醛席夫碱配合物的合成、表征与抗氧化作用[J].化学研究,2015,26(1):35-38.
[16]PAN Sufang,YANG Guoyu,XU Cuilian,et al. Antioxidant Function of Chitooligosaccharides Salicylaldehyde Schiff Base Series[J]. J Henan Agric Univ,2012,46(6):687-690(in Chinese).潘素芳,杨国玉,徐翠莲,等.壳寡糖水杨醛系列席夫碱的抗氧化作用[J].河南农业大学学报,2012,46(6):687-690.
[17]Mamdouh S M,Alaa E A,Gehan S E,et al. Structural and Thermal Studies on Some Morpholine Complexes[J]. J Mol Struct,2019,1175:648-662.
[18]Sobhana B B,Abdul B A,Liu J,et al. Discovery of 3-Morpholino-imidazole[1,5-a]pyrazine BTK Inhibitors for Rheumatoid Arthritis[J]. Bioorg Med Chem Lett,2017,27(16):3939-3943.
[19]Li H M,Xu R,David C,et al. Design,Synthesis,and Structure Activity Relationship Studies of N-Arylsulfonyl Morpholines asγ-Secretase Inhibitors[J]. Bioorg Med Chem Lett,2010,20(22):6606-6609.
[20]Wu Y J,Jason G,Andrea M C,et al. Discovery of Morpholine-Based Aryl Sulfonamides as Nav1. 7 Inhibitors[J]. Bioorg Med Chem Lett,2018,28(5):958-962.
[21]Chan W H,Bruce M B,Joseph S W. Development of a Scalable Synthetic Route Towards a 2,2,6-Trisubstituted Chiral Morpholine via Stereoselective Hydroalkoxylation[J]. Tetra Lett,2018,29(19):1808-1812.
[22]Sun F M,Tian M K,Yang L,et al. Synthesis and Crystal Structure of Trans-4-[(5-(2,4-Dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyleneamino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones[J]. Chinese J Struct Chem,2008,27(7):789-792.
[2]Panneerselvam P,Nair R R,Vijayalakshmi G,et al. Synthesis of Schiff Bases of 4-(4-Aminophenyl)-morpholine as Potential Antimicrobial Agents[J]. Eur J Med Chem,2005,40(2):225-229.
[3]Kumari S,Chauhan G S. New Cellulose-Lysine Schiff-Base-Based Sensor-Adsorbent for Mercury Ions[J]. Appl Mater Interfaces,2014,6(8):5908-5917.
[4]Li C,Liu J C,Li Y R,et al. Synthesis and Antimicrobial Evaluation of 5-Aryl-1,2,4-triazole-3-thione Derivatives Containing a Rhodanine Moiety[J]. Bioorg Med Chem Lett,2015,25(15):3052-3056.
[5]LU Tianqi,WANG Po,RONG Zikun,et al. Synthesis and Optical Property of Schiff Base Containing Triphenylamine Group[J]. Chinese J Synth Chem,2017,25(12):1004-1007(in Chinese).鲁天琪,王坡,荣子鲲,等.一种含三苯胺基团的席夫碱的合成及其光学性[J].合成化学,2017,25(12):1004-1007.
[6]YUAN Zeli,WU Qing,YANG Xingbian,et al. Synthesis and Antibacterial Activity of Novel Schiff Base Macrocyclic Compounds Cotaining Triazole[J]. Chinese J Org Chem,2011,31(10):1698-1702.(in Chinese).袁泽利,吴庆,杨兴变,等.新型含均三唑席夫碱型大环化合物的合成及其抗菌活性[J].有机化学,2011,31(10):1698-1702.
[7]HE Qiangfang,WU Yinghong,CAI Zhijian,et al. Synthesis of Fluorescent Cross-Linked Stabilized Polymeric Micelles Based on Salicylidene Schiff Base/Zn2+Complexes and Sensor for Cu2+Detection[J]. Chinese J Appl Chem,2016,33(6):701-709(in Chinese).何强芳,吴映红,蔡志健,等.基于水杨醛席夫碱锌配合物交联稳定化荧光聚合物胶束的合成及其对铜离子的荧光响应性[J].应用化学,2016,33(6):701-709.
[8]Jin F,Pan C Y,Lu T Q,et al. Syntheses,Crystal Structures,DFT Calculation and Optical Properties of a Schiff Base and Its Dinuclear Mercury(Ⅱ)Complex[J]. Chinese J Struct Chem,2017,36(2):250-257.
[9]CAO Yi,LU Yun. Syntheses and Properties of Three Schiff Bases Containing Salicylaldehyde Units[J]. Chem Bull,2017,80(6):539-543(in Chinese).曹义,陆云.三种水杨醛类席夫碱的合成与性质研究[J].化学通报,2017,80(6):539-543.
[10]Shen Z H,Shi Y X,Yang M Y,et al. Synthesis,Crystal Structure,DFT Studies and Biological Activity of a Novel Schiff Base Containing Triazolo[4,3-a]pyridine Moiety[J]. Chinese J Struct Chem,2016,35(3):457-464.
[11]PAN Dingwu,DU Huan,LV Xinyang,et al. Synthesis and Antibacterial Activities of Novel Quinazoline-2,4-dione Derivatives Containing the 1,2,4-Triazole Schiff-Base Unit[J]. Chinese J Org Chem,2016,36(4):818-825(in Chinese).潘顶伍,杜欢,吕新阳,等.含1,2,4-三唑席夫碱的新型喹唑啉-2,4-二酮类衍生物的合成及其抗细菌活性研究[J].有机化学,2016,36(4):818-825.
[12]LI Yingjun,ZHANG Nan,JIN Kun,et al. Novel Carbazole-Thiosemicarbazide Based Schiff-Base Probes for Cu2+[J].Chinese J Org Chem,2017,37(10):2640-2646(in Chinese).李英俊,张楠,靳焜,等.新型基于咔唑-氨基硫脲席夫碱识别Cu2+的探针[J].有机化学,2017,37(10):2640-2646.
[13]Gao B J,Zhang D D,Li Y B. Synthesis and Photoluminescence Properties of Novel Schiff Base Type Polymer-Rare Earth Complexes Containing Furfural-Based Bidentate Schiff Base Ligands[J]. Opt Mater,2018,77:77-86.
[14]LIU Junhu,LIU Yong,JIAN Junyou,et al. Synthesis and Fungicidal Activities of Novel Quinazoline Derivatives Containing1,2,4-Triazole Schiff-Base Unit[J]. Chinese J Org Chem,2013,33:370-374(in Chinese).刘军虎,刘勇,蹇军友,等.含1,2,4-三唑席夫碱的新型喹唑啉类化合物的合成及其抗菌活性研究[J].有机化学,2013,33:370-374.
[15]XIE Qingfan,LU Huiqiang,YOU Xingying,et al. Synthesis,Characterization and Antioxidant Effect of Complexes from2-Aminomethyl Pyridine 5-Bromosalicylaldehyde Schiff base[J]. Chem Res,2015,26(1):35-38(in Chinese).解庆范,卢慧强,游兴英,等. 2-氨甲基吡啶缩5-溴水杨醛席夫碱配合物的合成、表征与抗氧化作用[J].化学研究,2015,26(1):35-38.
[16]PAN Sufang,YANG Guoyu,XU Cuilian,et al. Antioxidant Function of Chitooligosaccharides Salicylaldehyde Schiff Base Series[J]. J Henan Agric Univ,2012,46(6):687-690(in Chinese).潘素芳,杨国玉,徐翠莲,等.壳寡糖水杨醛系列席夫碱的抗氧化作用[J].河南农业大学学报,2012,46(6):687-690.
[17]Mamdouh S M,Alaa E A,Gehan S E,et al. Structural and Thermal Studies on Some Morpholine Complexes[J]. J Mol Struct,2019,1175:648-662.
[18]Sobhana B B,Abdul B A,Liu J,et al. Discovery of 3-Morpholino-imidazole[1,5-a]pyrazine BTK Inhibitors for Rheumatoid Arthritis[J]. Bioorg Med Chem Lett,2017,27(16):3939-3943.
[19]Li H M,Xu R,David C,et al. Design,Synthesis,and Structure Activity Relationship Studies of N-Arylsulfonyl Morpholines asγ-Secretase Inhibitors[J]. Bioorg Med Chem Lett,2010,20(22):6606-6609.
[20]Wu Y J,Jason G,Andrea M C,et al. Discovery of Morpholine-Based Aryl Sulfonamides as Nav1. 7 Inhibitors[J]. Bioorg Med Chem Lett,2018,28(5):958-962.
[21]Chan W H,Bruce M B,Joseph S W. Development of a Scalable Synthetic Route Towards a 2,2,6-Trisubstituted Chiral Morpholine via Stereoselective Hydroalkoxylation[J]. Tetra Lett,2018,29(19):1808-1812.
[22]Sun F M,Tian M K,Yang L,et al. Synthesis and Crystal Structure of Trans-4-[(5-(2,4-Dichlorophenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methyleneamino]-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-ones[J]. Chinese J Struct Chem,2008,27(7):789-792.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |