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Nanoporous AlSBA-15 catalysed Claisen–Schmidt condensation for the synthesis of novel and biologically active chalcones
Journal of Porous Materials ( IF 2.5 ) Pub Date : 2020-01-20 , DOI: 10.1007/s10934-019-00854-3
Palani Elamathi , Govindasamy Chandrasekar , M.M. Balamurali

Mesoporous AlSBA-15 catalysts (nSi/nAl ratios of 41, 129 and 210) were synthesized by sol–gel method. These materials were characterized by XRD, N2 sorption, FTIR, TPD-NH3, FESEM, EDX, and TEM analysis. XRD analysis of AlSBA-15 catalysts confirmed the existence of well-ordered crystalline structure having p6mm symmetry. N2 sorption isotherm of AlSBA-15 catalysts showed a type IV adsorption isotherm with H1 hysteresis loops. SEM analysis of AlSBA-15 (41) indicated worm-like particle morphology with a size range of 3 μm with co-occurrence of smaller particles of size ca. 1 μm. TEM analysis of AlSBA-15 (41) showed existence of uniform array of tubular nano-channels. The catalytic application of AlSBA-15 catalysts was tested on industrially important chalcones synthesis via Claisen–Schmidt condensation reaction in environment friendly approach. The reaction parameters such as time, temperature, nSi/nAl ratio, catalyst amount, and catalyst stability were investigated. AlSBA-15 (41) catalyst showed an excellent catalytic performance with 98% 1-tetralone conversion with 100% selectivity of compound 1c (91% yield) within 120 min AlSBA-15 (129) and AlSBA-15 (210) catalysts. The anti-oxidant activity of the synthesised chalcones were investigated by various in-vitro procedures, including radical scavenging potentials-1, 1-diphenyl-2-picryl-hydrazil, hydrogen peroxide scavenging, and ferric reducing potential assay. The new chalcone derivatives synthesised in this work showed a very good antioxidant activity and some were found to be more active than the parent chalcones, (E)-3-(4-hydroxy-3-methoxyphenyl)-1-phenylprop-2-en-1-one (compound 8c), and standard antioxidant (curcumin).



中文翻译:

纳米多孔AlSBA-15催化Claisen-Schmidt缩合反应合成新颖的具有生物活性的查耳酮

通过溶胶-凝胶法合成了介孔AlSBA-15催化剂(n Si / n Al比为41、129和210)。这些材料通过XRD,N 2吸附,FTIR,TPD-NH 3,FESEM,EDX和TEM分析进行表征。AlSBA-15催化剂的XRD分析证实存在具有p6mm对称性的井井有条的晶体结构。N 2AlSBA-15催化剂的吸附等温线显示具有H1磁滞回线的IV型吸附等温线。AlSBA-15(41)的SEM分析表明,蠕虫状颗粒的形态在3μm的范围内,同时存在尺寸约为ca的较小颗粒。1微米 AlSBA-15(41)的TEM分析表明存在管状纳米通道的均匀阵列。通过Claisen-Schmidt缩合反应以环境友好的方式测试了AlSBA-15催化剂在工业上重要的查耳酮合成中的催化应用。反应参数如时间,温度,n Si / n Al研究了催化剂的比例,催化剂量和催化剂稳定性。AlSBA-15(41)催化剂显示出优异的催化性能,在120分钟内AlSBA-15(129)和AlSBA-15(210)催化剂具有98%的1-四氢萘酮转化率和100%的化合物1c选择性(91%的收率)。合成的查耳酮的抗氧化活性通过各种体外方法进行了研究,包括自由基清除电位-1、1-二苯基-2-吡咯酰肼,过氧化氢清除和铁还原电位测定。在这项工作中合成的新查尔酮衍生物显示出非常好的抗氧化活性,并且发现其中一些比母体查尔酮(E)-3-(4-羟基-3-甲氧基苯基)-1-苯基丙-2-烯更具活性-1-one(化合物8c)和标准抗氧化剂(姜黄素)。

更新日期:2020-01-20
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