1,2,3-Triazole β-lactam Conjugates As Antimicrobial Agents

Overview

Journal Heliyon

Specialty Social Sciences

Date 2020 Jul 9

PMID 32637684

Citations 1

Authors

Rajneesh Kaur

Raman Singh

Antresh Kumar

Satvinder Kaur

Nitesh Priyadarshi

Nitin Kumar Singhal

Kuldeep Singh

Affiliations

Soon will be listed here.

Abstract

A convenient and efficient synthesis of new triazole β-lactam conjugates using click chemistry is described. β-lactam and were prepared using cycloaddition strategy and propargylated at -1 to afford compounds and . Cu-catalyzed click reaction of these β-lactams and with different aryl azides provided 1,2,3-triazole conjugates and , respectively. The products were fully characterized spectroscopically and tested against Gram-(+) and Gram-(-) bacteria. Compound and were found to be most active.

Citing Articles

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-]pyrazine Derivatives.

Hu Z, Dong H, Si Z, Zhao Y, Liang Y Molecules. 2023; 28(23).

PMID: 38067606 PMC: 10708386. DOI: 10.3390/molecules28237876.

References

Singh P, Sachdeva S, Raj R, Kumar V, Mahajan M, Nasser S . Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives. Bioorg Med Chem Lett. 2011; 21(15):4561-3. DOI: 10.1016/j.bmcl.2011.05.119. View

Dheer D, Singh V, Shankar R . Medicinal attributes of 1,2,3-triazoles: Current developments. Bioorg Chem. 2017; 71:30-54. DOI: 10.1016/j.bioorg.2017.01.010. View

Carosso S, Miller M . Syntheses and studies of new forms of N-sulfonyloxy β-lactams as potential antibacterial agents and β-lactamase inhibitors. Bioorg Med Chem. 2015; 23(18):6138-47. PMC: 4562877. DOI: 10.1016/j.bmc.2015.08.005. View

Tomasz A . The mechanism of the irreversible antimicrobial effects of penicillins: how the beta-lactam antibiotics kill and lyse bacteria. Annu Rev Microbiol. 1979; 33:113-37. DOI: 10.1146/annurev.mi.33.100179.000553. View

Lopez-Rojas P, Janeczko M, Kubinski K, Amesty A, Maslyk M, Estevez-Braun A . Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives. Molecules. 2018; 23(1). PMC: 6017388. DOI: 10.3390/molecules23010199. View

Durand G, Raoult D, Dubourg G . Antibiotic discovery: history, methods and perspectives. Int J Antimicrob Agents. 2018; 53(4):371-382. DOI: 10.1016/j.ijantimicag.2018.11.010. View

Haldon E, Nicasio M, Perez P . Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update. Org Biomol Chem. 2015; 13(37):9528-50. DOI: 10.1039/c5ob01457c. View

Kotha S, Goyal nee Bansal D, Banerjee S, Datta A . A novel di-triazole based peptide as a highly sensitive and selective fluorescent chemosensor for Zn2+ ions. Analyst. 2012; 137(12):2871-5. DOI: 10.1039/c2an35222b. View

Pitts C, Lectka T . Chemical synthesis of β-lactams: asymmetric catalysis and other recent advances. Chem Rev. 2014; 114(16):7930-53. DOI: 10.1021/cr4005549. View

10.

Bush K, Bradford P . Interplay between β-lactamases and new β-lactamase inhibitors. Nat Rev Microbiol. 2019; 17(5):295-306. DOI: 10.1038/s41579-019-0159-8. View

11.

Petrova K, Potewar T, Correia-da-Silva P, Barros M, Calhelha R, Ciric A . Antimicrobial and cytotoxic activities of 1,2,3-triazole-sucrose derivatives. Carbohydr Res. 2015; 417:66-71. DOI: 10.1016/j.carres.2015.09.003. View

12.

Yuan X, Lu P, Xue X, Qin H, Fan C, Wang Y . Discovery of 2-azetidinone and 1H-pyrrole-2,5-dione derivatives containing sulfonamide group at the side chain as potential cholesterol absorption inhibitors. Bioorg Med Chem Lett. 2016; 26(3):849-853. DOI: 10.1016/j.bmcl.2015.12.077. View

13.

Singh P, Raj R, Kumar V, Mahajan M, Bedi P, Kaur T . 1,2,3-Triazole tethered β-lactam-chalcone bifunctional hybrids: synthesis and anticancer evaluation. Eur J Med Chem. 2011; 47(1):594-600. DOI: 10.1016/j.ejmech.2011.10.033. View

14.

Arya N, Jagdale A, Patil T, Yeramwar S, Holikatti S, Dwivedi J . The chemistry and biological potential of azetidin-2-ones. Eur J Med Chem. 2014; 74:619-56. DOI: 10.1016/j.ejmech.2014.01.002. View

15.

Neu H . Aztreonam: the first monobactam. Med Clin North Am. 1988; 72(3):555-66. DOI: 10.1016/s0025-7125(16)30758-1. View

16.

Kumar K, Pradines B, Madamet M, Amalvict R, Kumar V . 1H-1,2,3-triazole tethered mono- and bis-ferrocenylchalcone-β-lactam conjugates: synthesis and antimalarial evaluation. Eur J Med Chem. 2014; 86:113-21. DOI: 10.1016/j.ejmech.2014.08.053. View

17.

Sumangala V, Poojary B, Chidananda N, Fernandes J, Suchetha Kumari N . Synthesis and antimicrobial activity of 1,2,3-triazoles containing quinoline moiety. Arch Pharm Res. 2010; 33(12):1911-8. DOI: 10.1007/s12272-010-1204-3. View

18.

Decuyper L, Jukic M, Sosic I, Zula A, Dhooghe M, Gobec S . Antibacterial and β-Lactamase Inhibitory Activity of Monocyclic β-Lactams. Med Res Rev. 2017; 38(2):426-503. DOI: 10.1002/med.21443. View

19.

NAYLER J . Early discoveries in the penicillin series. Trends Biochem Sci. 1991; 16(5):195-7. DOI: 10.1016/0968-0004(91)90076-8. View

20.

Deketelaere S, Van Nguyen T, Stevens C, Dhooghe M . Synthetic Approaches toward Monocyclic 3-Amino-β-lactams. ChemistryOpen. 2017; 6(3):301-319. PMC: 5474669. DOI: 10.1002/open.201700051. View