Synthesis, anti-microbial evaluation, and in silico studies of novel quinoline-isoxazole hybrids

被引:1
作者
Mandir, Deep P. [1 ]
Mandir, Shivani D. [2 ]
Kamdar, Jignesh H. [3 ]
Tala, Satishkumar D. [1 ]
机构
[1] Atmiya Univ, Fac Sci, Dept Chem Sci, Kalawad Rd, Rajkot 360005, Gujarat, India
[2] Atmiya Univ, Fac Sci, Dept Biotechnol, Rajkot, India
[3] RK Univ, Sch Sci, Dept Microbiol, Insil Lab, Rajkot, India
关键词
Anti-fungal activity; anti-microbial activity; isoxazole; molecular docking; quinoline; MOLECULAR-DYNAMICS SIMULATIONS; BIOLOGICAL EVALUATION; ANTIBACTERIAL; DERIVATIVES; ANTIMYCOBACTERIAL; ANTICONVULSANT; RESISTANCE; INHIBITORS; ANALOGS; BINDING;
D O I
10.1080/00397911.2024.2397813
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel quinoline-isoxazole hybrids 6a-o has been synthesized via multistep synthetic approach involving hetero Diels-alder reaction strategy. The target compounds were obtained in good yield, using low-cost readily available starting materials using simple reaction conditions. The newly synthesized compounds were confirmed using H-1 NMR,C-13 NMR, and Mass spectroscopic analysis techniques. Further, compounds 6a-o were subjected to in vitro antimicrobial screening against various bacterial and fungal strains, such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Salmonella typhi, Aspergillus niger, and Candida albicans. Among these, compounds 6i, 6j, and 6 l were found most active having equally potent compared to standard drug Ampicillin and Gentamycin. Moreover, in silico studies of 6a-o with E. coli DNA gyrase through molecular docking and MD simulations showed excellent binding properties of these derivatives with protein site.
引用
收藏
页码:1603 / 1619
页数:17
相关论文
共 45 条
[1]   Synthesis and Evaluation of the Antibacterial and Antioxidant Activities of Some Novel Chloroquinoline Analogs [J].
Abdi, Bayan ;
Fekadu, Mona ;
Zeleke, Digafie ;
Eswaramoorthy, Rajalakshmanan ;
Melaku, Yadessa .
JOURNAL OF CHEMISTRY, 2021, 2021
[2]   Synthesis of some new pyrazolo[3,4-d]pyrimidines and thiazolo [4,5-d]pyrimidines and evaluation of their antimicrobial activities [J].
Akbari, J. D. ;
Tala, S. D. ;
Dhaduk, M. F. ;
Joshi, H. S. ;
Mehta, K. B. ;
Pathak, S. J. .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (06) :1471-1477
[3]   A metal-free approach for in situ regioselective synthesis of isoxazoles via 1,3 dipolar cycloaddition reaction of nitrile oxide with propargyl bromide [J].
Aleti, Rajeshwar Reddy ;
Cherukupalli, Srinivasulu ;
Dhawan, Sanjeev ;
Kumar, Vishal ;
Girase, Pankaj S. ;
Mohite, Sachin ;
Karpoormath, Rajshekhar .
CHEMICAL PAPERS, 2022, 76 (05) :3005-3010
[4]   Effects of new tetrahydroquinoline-isoxazole hybrids on bioenergetics of hepatocarcinoma Hep-G2 cells and rat liver mitochondria [J].
Alvarez Santos, Marilyn Rocio ;
Bueno Duarte, Yenny ;
Guiza, Fausto M. ;
Romero Bohorquez, Arnold R. ;
Carolina Mendez-Sanchez, Stelia .
CHEMICO-BIOLOGICAL INTERACTIONS, 2019, 302 :164-171
[5]  
[Anonymous], 2023, Antimicrobial Resistance: Global Report on Surveillance
[6]  
Bakht J, 2014, PAK J PHARM SCI, V27, P139
[7]   Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramofecular domino hetero Diels-Alder reactions of 1-oxa-1,3-butadienes in aqueous medium [J].
Baruah, Biswajita ;
Bhuyan, Pulak J. .
TETRAHEDRON, 2009, 65 (34) :7099-7104
[8]   Synthesis and DNA cleavage studies of novel quinoline oxime esters [J].
Bindu, P. J. ;
Mahadevan, K. M. ;
Satyanarayan, N. D. ;
Naik, T. R. Ravikumar .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) :898-900
[9]   Synthesis of Fused Isoxazoles of Iodoquinol as in vitro EGFR Aiming Anticancer Agents [J].
Bokkala, Karthik ;
Bapuram, Ashok Kumar ;
Thirukovela, Narasimha Swamy ;
Nukala, Satheesh Kumar .
CHEMISTRYSELECT, 2024, 9 (01)
[10]  
Childers MC, 2017, MOL SYST DES ENG, V2, P9, DOI [10.1039/C6ME00083E, 10.1039/c6me00083e]