Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives

Krolenko, Konstantin Yu.; Vlasov, Sergiy V.; Журавель, И. А.

doi:10.1007/s10593-016-1972-x

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…Literature survey reveals the synthesis of 1,3,4‐oxadiazole derivatives as antibacterial agents . However, there are very few reports on the antibacterial activity of 1,2,4‐oxadiazole derivatives, which encouraged us to move further . Various methods reported for the preparation of 1,2,4‐oxadiazoles such as cyclization of O ‐acylamidoximes obtained from acylation of amidoximes with acyl halides, esters, or anhydrides .…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Rapid and Efficient Synthesis of New Series of Chromene‐Based 1,2,4‐Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation

Baral

Mohapatra

Raiguru

et al. 2018

Journal of Heterocyclic Chem

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The current study aimed to identify a new strategy of FeCl3 catalyzed multicomponent synthesis of substituted 2H‐chromene–fused pyrrole derivatives. A series of chromene‐based pyrrole prepared by employing an array of 3‐nitro‐2H‐chromenes, aniline, and acetylacetone in toluene under microwave irradiation. Using FeCl3 as a prompt catalyst and microwave irradiation to synthesize 2H‐chromene–fused pyrrole motifs significantly reduces the reaction time and facilitates to high yields (83%‐95%). Structure of all synthesized compounds analyzed by spectroscopic analysis. One‐pot reaction, short reaction period, and simple experimental procedure are the fascinating properties associated with this protocol. The in vitro antibacterial activity of the entire series was assessed against Staphylococcus aureus and Escherichia coli. Out of all the compounds, 15b and 15h revealed most excellent potency against both the bacterial strains relative to the reference gentamicin. Docking study was employed to determine the possible binding orientation of DNA gyrase with the active sites of chromene‐fused pyrrole analog. The docking results show that compounds 15b and 15h have higher binding affinity with energy −8.00 and −8.80 kcal/mol. These results illuminate the mode of binding progression and provide an esteemed pathway for the design and the structural modification of chromene‐fused pyrroles as a newly advanced class of antibacterial agent.

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Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Rapid and Efficient Synthesis of New Series of Chromene‐Based 1,2,4‐Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation

Baral

Mohapatra

Raiguru

et al. 2018

Journal of Heterocyclic Chem

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“…In the recent study of Krolenko K. et al a new series of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives as antimicrobial agents have been synthesized and examined by agar diffusion test against Gram-positive (S. aureus, B. subtilis, E. coli) and Gram-negative bacteria (P. vulgaris, P. aeruginosa) as well as fungi (C. albicans). Amongst three different series, compound 25 (Table 3) exhibited the highest biological activity with grow inhibition zone in a range of 20-25 mm, better than reference compounds-metronidazole and syntomycin-commonly used antibiotics (grow inhibition zone of 14-17 mm) [104]. Despite the high potential of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives, no further work has been published.…”

Section: Antimicrobial Agentsmentioning

confidence: 99%

Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery

et al. 2020

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Five-membered 1,2,4-oxadiazole heterocyclic ring has received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the novel drug development. After a century since the 1,2,4-oxadiazole have been discovered, the uncommon potential attracted medicinal chemists’ attention, leading to the discovery of a few presently accessible drugs containing 1,2,4-oxadiazole unit. It is worth noting that the interest in a 1,2,4-oxadiazoles’ biological application has been doubled in the last fifteen years. Herein, after a concise historical introduction, we present a comprehensive overview of the recent achievements in the synthesis of 1,2,4-oxadiazole-based compounds and the major advances in their biological applications in the period of the last five years as well as brief remarks on prospects for further development.

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“…GC-MS profiling of ethyl acetate extract reported with the bioactive compounds majorly pthalic acids-1,2-benzene dicarboxylic acid renowned for antibacterial, antifungal and antiviral activities, [27] geranyl linalool also reported which is commercially important as an essential oil, as an antimicrobial agent [28] and 1,2,4-oxadiazole, 3-(1,3-bezodioxol-5-y)-5-[2-(4methoxyphenyl)ethyl] which are potent antibacterial compounds reported in C. ramosissima for the first time where 1,2,4-oxidiazole derivatives exhibited antibacterial activity against X. oryzae. In previous report these compounds are known to have other properties like antiviral, antifugal [29,30] also which has unexplored activities in these compound. In previous studies other species, C. sessiflora reported for remarkable antibacterial activity against Pseudomonas species.…”

Section: Antibacterial Activity Mic and Tlc Bioautographymentioning

confidence: 99%

Analysis of phytochemical constituents, antibacterial, antioxidant and GC-MS profiling of <i>Crotalaria ramosissima</i> leaf extracts

HA,

Garampalli

2024

Int. J. Pharm. Sci. Drug Res.

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Crotalaria ramosissima Roxb. (Fabales: Fabaceae) is a common weed that grows prolifically in few areas of Karnataka, plant used as insect repellent in grain storage room and C. ramosissima leaves used to treat skin diseases. The purpose of study was to investigate phytochemical constituents and evaluate their antibacterial and antioxidant properties along with bioactive compound profiling. Phytochemical screening of ethyl acetate, ethanol and methanol extracts revealed presence of necessary phytochemical components, anti-microbial activity against plant pathogens showed best results from ethyl acetate extract with MIC 15.60µg mL-1 against Pseudomonas syringae and Xanthomonas oryzae with MIC 31.25µg mL-1, confirmed with TLC bio-autography, DPPH antioxidant assay, showed the highest activity of IC-50 2.71µg mL-1 from methanol extract with standard reference, Gas chromatography/Mass spectroscopy (GC-MS) used for profiling to detect chemical compounds from plant solvent extracts which showed presence of 21 compounds, ethyl acetate extract identified with 1,2,4-Oxidiazole, 3-(1,3-bezodioxol-5-y-5-[2-(4-methoxyphenyl)-ethyl] which is heterocyclic aromatic compound of azole family-alkaloid, which is reported for the first time in C. ramosissima. The results revealed significant properties and the obtained 1,2,4-oxidiazole derivative can be a novel bio-control agent against microorganisms and for crop protection. It also retained current researcher's attention from its biological properties in pharmaceutical drug industry.

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Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives

Cited by 6 publications

References 15 publications

Microwave‐Assisted Rapid and Efficient Synthesis of New Series of Chromene‐Based 1,2,4‐Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation

Microwave‐Assisted Rapid and Efficient Synthesis of New Series of Chromene‐Based 1,2,4‐Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation

Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery

Analysis of phytochemical constituents, antibacterial, antioxidant and GC-MS profiling of <i>Crotalaria ramosissima</i> leaf extracts

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