一锅法无催化剂合成新型曲酸标记的2-芳基/烷基取代-4H-色烯及其抗菌和抗生物膜活性评价

One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities.

作者信息

Bingi Chiranjeevi, Emmadi Narender Reddy, Chennapuram Madhu, Poornachandra Y, Kumar C Ganesh, Nanubolu Jagadeesh Babu, Atmakur Krishnaiah

机构信息

Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.

出版信息

Bioorg Med Chem Lett. 2015 May 1;25(9):1915-9. doi: 10.1016/j.bmcl.2015.03.034. Epub 2015 Mar 20.

DOI:10.1016/j.bmcl.2015.03.034

PMID:25838145

Abstract

A number of 3-hydroxy-6-(hydroxymethyl)-2-(2-phenyl-4H-chromen-4-yl)-4H-pyran-4-ones (3) have been synthesized in a one pot catalyst free reaction of 2-hydroxy chalcone (1) with kojic acid (2) in toluene at reflux temperature and evaluated for antimicrobial and anti-biofilm activities. Compounds 3a, 3e, 3f, 3l showed potent antimicrobial activity against Staphylococcus aureus MLS-16 MTCC 2940, Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, whereas 3b and 3k exhibited excellent activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739, while 3g showed promising activity against Bacillus subtilis MTCC 121 and Escherichia coli MTCC 739. On the other hand, compounds 3a, 3b and 3l showed very good anti-biofilm activity and 3g showed moderate activity against Bacillus subtilis MTCC 121. Whereas, compounds 3a and 3f showed moderate activity against Escherichia coli MTCC 739, while compounds 3a, 3b, 3k and 3l displayed similar activity against Staphylococcus aureus MLS-16 MTCC 2940.

摘要

通过2-羟基查尔酮（1）与曲酸（2）在甲苯中于回流温度下进行一锅无催化剂反应，合成了一系列3-羟基-6-（羟甲基）-2-（2-苯基-4H-色烯-4-基）-4H-吡喃-4-酮（3），并对其抗菌和抗生物膜活性进行了评估。化合物3a、3e、3f、3l对金黄色葡萄球菌MLS-16 MTCC 2940、枯草芽孢杆菌MTCC 121和大肠杆菌MTCC 739显示出强效抗菌活性，而3b和3k对枯草芽孢杆菌MTCC 121和大肠杆菌MTCC 739表现出优异活性，3g对枯草芽孢杆菌MTCC 121和大肠杆菌MTCC 739显示出有前景的活性。另一方面，化合物3a、3b和3l表现出非常好的抗生物膜活性，3g对枯草芽孢杆菌MTCC 121表现出中等活性。而化合物3a和3f对大肠杆菌MTCC 739表现出中等活性，化合物3a、3b、3k和3l对金黄色葡萄球菌MLS-16 MTCC 2940表现出相似活性。

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一锅法无催化剂合成新型曲酸标记的2-芳基/烷基取代-4H-色烯及其抗菌和抗生物膜活性评价

One-pot catalyst free synthesis of novel kojic acid tagged 2-aryl/alkyl substituted-4H-chromenes and evaluation of their antimicrobial and anti-biofilm activities.

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