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Microwave assisted one-pot green synthesis of cinnoline derivatives inside natural sporopollenin microcapsules

机译:微波炉辅助一锅绿色合成天然孢子蛋白微胶囊内的脑油衍生物

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摘要

We present a green and efficient approach for the synthesis of novel cinnoline derivatives inside natural Lycopodium clavatum sporopollenin (LCS) microcapsules via a one-pot microwave (MW) assisted reaction for the first time. We also propose the concept that the robust micrometre-sized sporopollenin microcapsules can act as MW microreactors. We demonstrate the feasibility of this concept by in situ synthesising 8-hydroxy-7-nitro-6-(3-nitrophenyl)-3-oxo-2-(p-tolyl)-2,3,5,6-tetrahydrocinnoline-4-carbonitrile inside the LCS microcapsules via a microwave (MW) assisted reaction of ethyl 5-cyano-4-methyl-6-oxo-1-(p-tolyl)-1,6-dihydropyridazine-3-carboxylate with 1-nitro-2-phenylethylene in the presence of piperidine as a base at 100 degrees C for 20 minutes. The LCS microparticles are extensively characterised before and after the MW induced reaction using several techniques. The formation of the cinnoline compound inside the LCS microcapsules is confirmed by laser scanning confocal microscopy (LSCM), X-ray diffraction (XRD) and fourier-transform infrared spectroscopy (FTIR) analyses. Using liquid chromatography-mass spectrometry (LCMS) analyses, we show that the structural integrity of the cinnoline compound, recovered from the cinnoline loaded (cinn-loaded) LCS, is preserved. The pure cinnoline is found to show promising optical properties with two (max) absorption peaks at 310 and 610 nm. Both the pure cinnoline and cinn-loaded LCS show promising antibacterial activity against Pseudomonas aeruginosa (Gram-negative) and Bacillus cereus (Gram-negative) human pathogenic bacterial strains. The successful MW induced reaction of the prominent cinnoline derivative inside the biocompatible LCS microreactors can open up intriguing applications in materials and pharmaceutical sciences.
机译:我们首次通过单罐微波(MW)辅助反应在天然氯氰酸钙孢囊蛋白(LCS)微胶囊中合成新型肉碱衍生物的绿色和有效的方法。我们还提出了强大的微米尺寸的孢子蛋白微胶囊可以充当MW微孔剂的概念。我们通过原位展示该概念的可行性,以原位合成8-羟基-7-NITRO-6-(3-硝基苯基)-3-氧代-2-(对甲苯基)-2,3,5,6-四氢碱-4 - 通过微波(MW)微胶囊在LCS微胶囊内的碳氮溶液5-氰基-4-甲基-6-氧代-1-(对甲苯基)-1,6-二氢吡啶嗪-3-羧酸盐,1-硝基 - 2-苯基乙烯在哌啶存在下作为碱在100℃下施用20分钟。使用几种技术,LCS微粒在MW诱导反应之前和之后进行广泛表征。通过激光扫描共聚焦显微镜(LSCM),X射线衍射(XRD)和傅立叶 - 变换红外光谱(FTIR)分析来确认LCS微胶囊内的肉桂啉化合物的形成。采用液相色谱 - 质谱(LCMS)分析,我们表明,从肉桂碱上回收(CINN-LOADED)LCS的肉碱化合物的结构完整性。发现纯cinnoline在310和610nm处显示有前景的光学性质,具有两个(最大)吸收峰。纯cinnoline和Cinn-Loaded的LC均显示出对铜绿假单胞菌(革兰氏阴性)和芽孢杆菌(革兰氏阴性)的人致病性细菌菌株的有前途的抗菌活性。成功的MW诱导的生物相容性LCS微反应器内突出的肉瘤衍生物的反应可以在材料和药学中开辟有趣的应用。

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  • 来源
    《RSC Advances》 |2018年第41期|共11页
  • 作者单位

    Menia Univ Fac Sci Dept Chem Al Minya 61519 Egypt;

    Menia Univ Fac Sci Dept Chem Al Minya 61519 Egypt;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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