文章摘要
二茂铁基咪唑并[1,2-a]吡啶化合物的合成及抗氧化性能
Synthesis and Antioxidant Properties of Ferrocenyl Imid-azo[1,2-a]pyridine Compounds
投稿时间:2019-06-16  修订日期:2019-07-09
DOI:
中文关键词: Groebke-Blackburn-Bienaym?反应  二茂铁基咪唑并[1,2-a]吡啶  抗氧化  自由基
英文关键词: Groebke-Blackburn-Bienaym? reaction  ferrocenyl imidazo[1,2-a]pyridine  antioxidant  free radical
基金项目:
作者单位E-mail
席高磊 河南中烟工业有限责任公司技术中心 xigaoleijida@126.com 
魏甲欣 河南中烟工业有限责任公司许昌卷烟厂 wei61391@sina.com 
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中文摘要:
      以乙醇为溶剂,在加热条件下采用LaCl3催化2-氨基吡啶、二茂铁甲醛和异氰之间的Groebke-Blackburn-Bienaym?三组分反应(GBB-3CR)合成5个二茂铁基咪唑并[1,2-a]吡啶化合物。利用核磁共振氢谱(proton magnetic resonance,1H NMR)、核磁共振碳谱(carbon-13 magnetic resonance,13C NMR)和超高效液相色谱-电喷雾离子源质谱联用仪(ultra high performance liquid chromatograph electrospray ion source mass spectrometer,UHPLC-ESI-MS)对合成产物结构进行了表征,并通过抑制HO?和还原型谷胱甘肽自由基(glutathione,GS?)引发的DNA氧化反应体系对化合物的抗氧化活性进行了检测,采用淬灭2,2?-偶氮-双-(3-乙基苯并噻唑啉-6-磺酸)二铵盐自由基(2,2’-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical,ABTS?)和二苯苦味酰肼自由基(2,2’-diphenyl-1-picrylhydrazyl,DPPH?)体系探索了化合物还原自由基的能力,进而探究了取代基对二茂铁基咪唑并[1,2-a]吡啶抗化合物氧化性能的影响。结果表明:5个目标化合物不仅能够有效地抑制自由基引发的DNA氧化反应,也能捕获自由基,是一类潜在的抗氧化剂。其中,在抑制HO?引发的DNA氧化反应体系中,5个化合物相对空白TBARS吸光度百分数可达65.4%~93.7%;在抑制GS?引发的DNA氧化反应体系中,5个化合物相对空白TBARS吸光度百分数可达25.6%~62.5%;5个二茂铁基咪唑并[1,2-a]吡啶化合物均能够捕获ABTS?和DPPH?两种自由基;双二茂铁基化合物VI抑制自由基引发的DNA氧化反应活性和捕获自由基能力优于其它化合物。
英文摘要:
      Five ferrocenyl imidazo[1,2-a]pyridine compounds were synthesized by Groeb-ke-Blackburn-Bienaym? three-component-reaction (GBB-3CR) among 2-aminopyridine, ferro-cenecarboxaldehyde, and isocyanide with LaCl3 being catalyst in ethanol. The structure of the com-pounds were confirmed by proton magnetic resonance (1H NMR), carbon-13 magnetic resonance (13C NMR), and ultra high performance liquid chromatograph electrospray ion source mass spec-trometer (UHPLC-ESI-MS). Antioxidant abilities of the obtained compounds were evaluated by in-hibiting HO?- and Cu2 /glutathione (GSH)-induced oxidation of DNA. The radical-scavenging prop-erties of the obtained compounds were estimated by quenching 2,2?-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS?) and 2,2?-diphenyl- 1-picrylhydrazyl (DPPH?), and then the effects of substituents on the antioxidant properties of fer-rocenyl imidazo[1,2-a]pyridine compounds could be explored. The results showed that the TBARS percentages of five compounds were 65.4%~93.7% in inhibiting HO?- induced oxidation of DNA. The TBARS percentages of five compounds were 25.6%~62.5% in inhibiting GS?- induced oxidation of DNA. All five ferrocenyl imidazo[1,2-a]pyridine compounds could scavenge ABTS? and DPPH?. The compounds VI containing two ferrocenyls exhibits higher activity than other compounds in quenching radicals and inhibiting radicals induced oxidation of DNA.
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