Antimicrobial and antiprotozoal activity of 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines: a review

Paruch, Kinga; Popiołek, Łukasz; Wujec, Monika

doi:10.1007/s00044-019-02463-w

Cited by 31 publications

(16 citation statements)

References 32 publications

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“…Various oxadiazole derivatives are subjected to synthesis under microwave irradiation, and their biological activities are reported that include antibacterial, antifungal, antiviral, anticonvulsant, antitumor, antimalarial, antitubercular, anti-asthmatic, antidepressant, antidiabetic, antioxidant, antiparkinsonian, analgesic and antiinflammatory, etc. ( Figure 6 ) [ 39 , 40 , 41 , 42 , 43 , 44 ].…”

Section: Microwave-assisted Synthesis Of Biologically Active Oxadimentioning

confidence: 99%

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

et al. 2021

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Green synthetic protocol refers to the development of processes for the sustainable production of chemicals and materials. For the synthesis of various biologically active compounds, energy-efficient and environmentally benign processes are applied, such as microwave irradiation technology, ultrasound-mediated synthesis, photo-catalysis (ultraviolet, visible and infrared irradiation), molecular sieving, grinding and milling techniques, etc. Thesemethods are considered sustainable technology and become valuable green protocol to synthesize new drug molecules as theyprovidenumerous benefits over conventional synthetic methods.Based on this concept, oxadiazole derivatives are synthesized under microwave irradiation technique to reduce the formation of byproduct so that the product yield can be increased quantitatively in less reaction time. Hence, the synthesis of drug molecules under microwave irradiation follows a green chemistry approach that employs a set of principles to minimize or remove the utilization and production of hazardous toxic materials during the design, manufacture and application of chemical substances.This approach plays a major role in controlling environmental pollution by utilizing safer solvents, catalysts, suitable reaction conditions and thereby increases the atom economy and energy efficiency. Oxadiazole is a five-membered heterocyclic compound that possesses one oxygen and two nitrogen atoms in the ring system.Oxadiazole moiety is drawing considerable interest for the development of new drug candidates with potential therapeutic activities including antibacterial, antifungal, antiviral, anticonvulsant, anticancer, antimalarial, antitubercular, anti-asthmatic, antidepressant, antidiabetic, antioxidant, antiparkinsonian, analgesic and antiinflammatory, etc. This review focuses on different synthetic approaches of oxadiazole derivatives under microwave heating method and study of their various biological activities.

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Section: Microwave-assisted Synthesis Of Biologically Active Oxadimentioning

confidence: 99%

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

et al. 2021

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“…Bearing in mind the above-mentioned problems, we conducted a literature review that showed that 3-acetyl-1,3,4-oxadiazoline derivatives constitute the class of compounds with high biological potential [8]. A simple method of the synthesis and a broad spectrum of activity make them an intensively studied group [9].…”

Section: Introductionmentioning

confidence: 99%

“…According to the literature, antibacterial [11][12][13][14][15][16], antifungal [17][18][19][20], anticancer [21][22][23], antimycobacterial [24][25][26][27] and antiprotozoal [28,29] effects of 1,3,4-oxadiazoles have been documented. Currently, there are no registered medicines with an acetyl substituent in the 1,3,4-oxadiazole ring, but there are medicines with an 1,3,4-oxadiazole moiety, such as Furamizole, Nesapidil, Zibotentan, Raltegravir or Tiodazosin [8]. The introduction of an acetyl group in the third position of the 1,3,4-oxadiazole ring seems to be an interesting solution, especially with regard to the fact that many studies showed that it can induce antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Biological Activity, Lipophilicity and Cytotoxicity of Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines

Paruch

Biernasiuk

Berecka‐Rycerz

et al. 2021

IJMS

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Antibiotic resistance is now a global problem, and the lack of effective antimicrobial agents for the treatment of diseases caused by resistant microbes is increasing. The 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines presented in this article may provide a good starting point for the development of potential new effective antimicrobial agents useful in the treatment of bacterial and fungal infections. Particular attention is drawn to the 1,3,4-oxadiazole derivative marked with the number 29 with 5-nitrofuran-2-yl substituent in its chemical structure. This substance showed a strong bactericidal effect, especially against Staphylococcus spp., and no cytotoxicity to the L929 normal cell line.

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“…Recent research conducted in our group has revealed that 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines show significant bioactivity [ 8 , 9 ]. These derivatives have a broad spectrum of activity mainly: antibacterial [ 10 , 11 , 12 , 13 , 14 , 15 ], antifungal [ 16 , 17 , 18 , 19 ], antitubercular [ 20 , 21 , 22 ], antiprotozoal [ 23 , 24 ], anti-cancer [ 25 , 26 , 27 , 28 ], antioxidant [ 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

“…The mechanism of the antibacterial action of 1,3,4-oxadiazoles may result from the presence of the –N=CO group in their structure and the transcription of genes involved in biofilm formation, such as SARA (regulator of gene expression), icaA (polysaccharide intercellular adhesion (PIA) or polymeric N -acetylglucosamine (PNAG) production), spa (surface protein for bacterial aggregation), fnbA (fibronectin-binding protein A) and fnbB (fibronectin-binding protein B). The gene necessary for biofilm formation in S. aureus as well as the main global regulator of the diverse range of virulence determinants in S. aureus [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines: Synthesis and Biological Activity

et al. 2020

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The aim of our study was the two-stage synthesis of 1,3,4-oxadiazole derivatives. The first step was the synthesis of hydrazide–hydrazones from 3-methyl-4-nitrobenzhydrazide and the corresponding substituted aromatic aldehydes. Then, the synthesized hydrazide–hydrazones were cyclized with acetic anhydride to obtain new 3-acetyl-2,3-disubstituted-1,3,4-oxadiazolines. All of obtained compounds were tested in in vitro assays to establish their potential antimicrobial activity and cytotoxicity. Our results indicated that few of the newly synthesized compounds had some antimicrobial activity, mainly compounds 20 and 37 towards all used reference bacterial strains (except Klebsiella pneumoniae, Proteus mirabilis, and Pseudomonas aeruginosa) and fungi. These substances showed a strong or powerful bactericidal effect, especially against Staphylococcus spp. belonging to Gram-positive bacteria. Compound 37 was active against Staphylococcus epidermidis at minimal inhibitory concentration (MIC) = 0.48 µg/mL and was characterized by low cytotoxicity. This compound possessed quinolin-4-yl substituent in the second position of 1,3,4-oxadiazole ring and 3-methyl-4-nitrophenyl in position 5. High effectiveness and safety of these derivatives make them promising candidates as antimicrobial agents. Whereas the compound 20 with the 5-iodofurane substituent in position 2 of the 1,3,4-oxadiazole ring showed the greatest activity against S. epidermidis at MIC = 1.95 µg/mL.

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Antimicrobial and antiprotozoal activity of 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines: a review

Cited by 31 publications

References 32 publications

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives

Biological Activity, Lipophilicity and Cytotoxicity of Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines

Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines: Synthesis and Biological Activity

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