Synthesis, molecular docking, DFT study, and in vitro antimicrobial activity of some 4-(biphenyl-4-yl)-1,4-dihydropyridine and 4-(biphenyl-4-yl)pyridine derivatives

被引:35
作者
Malani, Alimamad [1 ]
Makwana, Atul [1 ]
Monapara, Jahnvi [2 ,3 ]
Ahmad, Iqrar [4 ]
Patel, Harun [4 ]
Desai, Nisheeth [2 ,3 ]
机构
[1] Gujarat Univ, St Xaviers Coll Autonomous, Dept Chem, Ahmadabad, Gujarat, India
[2] Maharaja Krishnakumarsinhji Bhavnagar Univ, DST FIST Sponsored, Dept Chem, Div Med Chem, Mahatma Gandhi Campus, Bhavnagar 364002, Gujarat, India
[3] Maharaja Krishnakumarsinhji Bhavnagar Univ, UGC NONSAP, Mahatma Gandhi Campus, Bhavnagar 364002, Gujarat, India
[4] RC Patel Inst Pharmaceut Educ & Res, Div Comp Aided Drug Design, Dept Pharmaceut Chem, Dhule, Maharashtra, India
关键词
antimicrobial activity; DFT study; Hantzsch pyridine synthesis; molecular docking; Suzuki coupling reaction; 1,4-DIHYDROPYRIDINE DERIVATIVES; DESIGN; COMPLEXES;
D O I
10.1002/jbt.22903
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The evolution of microbial resistance necessitates the development of new antimicrobial drugs that are more effective than those currently on the market. To address this problem, we have prepared a series of novel 4-(biphenyl-4-yl)-1,4-dihydropyridine and 4-(biphenyl-4-yl)pyridine derivatives via Hantzsch reaction using nine different compounds containing active methylene group. IR, NMR, and mass spectra were used to determine the structures. Using ampicillin and griseofulvin as standards, the titled compounds were investigated for their antibacterial activity against different bacteria and fungi. Compounds 1f, 1g, 2f, and 2g have the best antibacterial activity against Gram-negative bacteria (minimum inhibitory concentration = 50 mu g/ml), while 1f, 1h, 2g, and 2h have high antifungal activity against Candida albicans (minimum inhibitory concentration = 100 mu g/ml). To gain a better understanding of the binding process and affinity for the bacterial Staphylococcus epidermidis protein, researchers used molecular docking and molecular mechanics, as well as the generalized Born model and solvent accessibility-based binding free energy. The active compounds 1g, 1h, and 2f have good docking scores of -5.575, -5.949, and -5.234, respectively, whereas compound 2c has the greatest docking score (-6.23). The HOMO-LUMO energy gap and molecular electrostatic potential were used to evaluate the reactivity of promising compounds, which were then associated with antibacterial efficacy.
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页数:12
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