Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility
Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility
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DOI：
10.1016/j.bmcl.2012.05.061
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发表时间：
2012-07-15
影响因子：
2.7
通讯作者：
Naik, Nagaraja
中科院分区：
文献类型：
--
作者：
Rangaswamy, Javarappa;Kumar, Honnaiah Vijay;Naik, Nagaraja
为了寻找一种高效的新型抗氧化抗菌剂，我们通过五步反应合成了一系列基于1,3,5-取代吡唑的苯并呋喃类似物（5a- 1）。最初，水杨醛的邻烷基衍生物在分子筛存在下，用1,8-双氮双环[5.4.0]十一-7-烯（DBU）处理，可以很容易地得到相应的2-乙酰基苯并呋喃2，产率很高。此外，醛醇与香兰素缩合，clisen - schmidt缩合反应与水合肼，然后取代苯胺偶联得到目标化合物。新合成的化合物通过IR、H-1 NMR、C-13 NMR、质量、元素分析等手段对其结构进行了确证，并对其抗氧化和抗菌活性进行了进一步筛选。其中化合物5d和5f表现出较好的抗氧化性能，其抑菌浓度比对照品高50%；化合物5h和5l在1.0和0.5 mg/mL浓度下分别比对照品、链霉素和氟康唑表现出较好的抑菌活性。(C) 2012 Elsevier Ltd.版权所有。
In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.