CuAAC-Mediated Synthesis and Antimicrobial Study of N-Acyl-Ampyrone-Linked 1,2,3-Triazoles

被引:0
作者
Lal, Bajrang [1 ]
Sharma, Kanika [1 ]
Tittal, Ram Kumar [1 ]
Lal, Kashmiri [2 ]
Yadav, Deepak [3 ]
Mathpati, Ramling S. [1 ]
机构
[1] Natl Inst Technol, Dept Chem, Kurukshetra 136119, Haryana, India
[2] Guru Jambheshwar Univ Sci & Technol GJUS&T, Dept Chem, Hisar 12500, Haryana, India
[3] Postgrad Inst Med Educ & Res PGIMER, Dept Expt Med & Biotechnol, Chandigarh 160012, India
来源
CHEMISTRYSELECT | 2025年 / 10卷 / 24期
关键词
N-Acyl-ampyrone-linked; 1; 2; 3-triazoles; Antimicrobial; CuAAC; Hemolytic analysis; Molecular docking; IN-VITRO; DERIVATIVES; DESIGN; ANTIOXIDANT; INHIBITORS; ANTIPYRINE; DOCKING; DRUGS;
D O I
10.1002/slct.202500126
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The high rate of sickness in humans is significantly impactedby the in effectiveness of treatments brought on by microbes that are resistantto several drugs. Consequently, the addition of novel antimicrobial drugs tothe arsenal of therapeutic options has the potential to be advantageous andmight be utilised as an important goal. To achieve this goal 1,2,3-triazolemotifs emerged as the most extensively examined moieties. In this context, wehave synthesized N-acyl-ampyrone-linked-1,2,3-triazoles utilizing the CuAAC"click" reaction. Synthesized triazoles were satisfactorily characterizedby FT-IR, 1H and 13C NMR, HR-MS, and single-crystal X-ray diffraction (compound 5n) data. The In vitro antimicrobial study was conducted againstfour different bacterial strains and two fungus strains. It was found thatcompound 5d exhibited a significant level of efficacy against all bacterialstrains. Furthermore, Compounds 5c, 5e, and 5g exhibited remarkable antifungal activity against Candida albicans, with minimum inhibitory concentrations (MIC) of0.0069, 0.0070, and 0.0070 mu M, respectively compared to fluconazole (MIC: 0.0408 mu M). In silico molecular docking investigations provided additionalsupport for the preliminary findings regarding antimicrobial results.
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页数:12
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共 65 条
[1]  
Abelian A., 2021, Applications of Heterocycles in the Design of Drugs and Agricultural Products, V134, P105
[2]   Synthesis, characterization, and anticancer activity of folate γ-ferrocenyl conjugatest [J].
Bertuzzi, Diego L. ;
Perli, Gabriel ;
Braga, Carolyne B. ;
Ornelas, Catia .
NEW JOURNAL OF CHEMISTRY, 2020, 44 (12) :4694-4703
[3]   Design, semi-synthesis and molecular docking of new antibacterial and antibiofilm triazole conjugates from hydroxy-triterpene acids and fluoroquinolones [J].
Boulila, Besma ;
Horchani, Mabrouk ;
Duval, Raphael ;
Othman, Mohamed ;
Daich, Adam ;
Ben Jannet, Hichem ;
Romdhane, Anis ;
Lawson, Ata Martin .
NEW JOURNAL OF CHEMISTRY, 2023, 47 (34) :15973-15986
[4]   1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview [J].
Bozorov, Khurshed ;
Zhao, Jiangyu ;
Aisa, Haji A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (16) :3511-3531
[5]   STUDIES ON V-TRIAZOLES .7. ANTI-ALLERGIC 9-OXO-1H,9H-BENZOPYRANO[2,3-D]-V-TRIAZOLES [J].
BUCKLE, DR ;
OUTRED, DJ ;
ROCKELL, CJM ;
SMITH, H ;
SPICER, BA .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (02) :251-254
[6]  
Burdulene D, 1999, PHARM CHEM J, V33, P191, DOI DOI 10.1007/BF02509936
[7]  
CLSI C., 2016, CLIN LAB STANDARDS I, V35, P16
[8]   Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates [J].
da Silva, Fernando de C. ;
de Souza, Maria Cecilia B. V. ;
Frugulhetti, Izabel I. P. ;
Castro, Helena C. ;
Souza, Silmara L. de O. ;
de Souza, Thiago Moreno L. ;
Rodrigues, Diego Q. ;
Souza, Alessandra M. T. ;
Abreu, Paula A. ;
Passamani, Fabiana ;
Rodrigues, Carlos R. ;
Ferreira, Vitor F. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) :373-383
[9]   Design, synthesis, structural characterization and in vitro evaluation of new 1,4-disubstituted-1,2,3-triazole derivatives against glioblastoma cells [J].
da Silva, Veronica D. ;
de Faria, Bruna M. ;
Colombo, Eduardo ;
Ascari, Lucas ;
Freitas, Gabriella P. A. ;
Flores, Leona S. ;
Cordeiro, Yraima ;
Romao, Luciana ;
Buarque, Camilla D. .
BIOORGANIC CHEMISTRY, 2019, 83 :87-97
[10]   SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules [J].
Daina, Antoine ;
Michielin, Olivier ;
Zoete, Vincent .
SCIENTIFIC REPORTS, 2017, 7