[4+2] Cycloaddition Mediated Stereoselective Synthesis of Tetrahydro-1H-Isobenzofuro Chromene Dione Derivatives: Antibacterial Evaluation and Molecular Docking Investigation

被引:2
作者
Parida, Sonali Priyadarshini [1 ]
Mohapatra, Suhasini [1 ]
Nayak, Sabita [1 ]
Mohapatra, Seetaram [1 ]
Panda, Jasmine [1 ]
Sahoo, Chita Ranjan [2 ]
机构
[1] Ravenshaw Univ, Dept Chem, Organ Synth Lab, Cuttack 753003, Odisha, India
[2] Govt India, ICMR Reg Med Res Ctr, Minist Hlth & Family Welf, Dept Hlth Res, Bhubaneswar 751023, Odisha, India
来源
CHEMISTRYSELECT | 2024年 / 9卷 / 35期
关键词
4+2] Cycloaddition reaction; Antibacterial activities; E.coli; S; aureus; Molecular docking; DNA GYRASE;
D O I
10.1002/slct.202402223
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient stereoselective synthesis of tetrahydro-1H-isobenzofuro[4,5-c]chromene-1,3(3aH)-dione derivatives were achieved through a novel [4+2] cycloaddition reaction of 4-styryl-2H-chromenes with cheaply available maleic anhydride. A series of new tetrahydro-1H-isobenzofuro[4,5-c]chromene-1,3(3aH)-dione derivatives 21(a-p) were synthesized in good to excellent yield under mild reaction condition with no chromatographic purification. In this reaction, the generation of four new consecutive stereogenic centers were determined by single crystal X-ray analysis. All the synthesized compounds were investigated further in silico and in vitro for antibacterial activities using two bacterial strain of DNA gyrase. Compounds 21 b and 21 j showed excellent docking score -9.3 kCal/mol and -8.6 kCal/mol with gram negative bacterial strain Escherichia coli (E. coli) with protein data bank (PDB ID) 3G7E. Out of all the tested molecules, 21 b and 21 j displayed good results with minimum inhibitory concentration 10 mu g/ml, 10 mu g/ml against the bacterial strain Escherichia coli(E. coli) and 10 mu g/ml, 20 mu g/ml against Staphylococcus aureus (S. aureus) respectively.
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页数:16
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