Synthesis And In Vitro Antimicrobial Activity Screening Of New 3‐Acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline Derivatives
Łukasz Popiołek, Anna Biernasiuk, Kinga Paruch, A. Malm, Monika Wujec
Published 2019 · Medicine, Chemistry
Twitter
Facebook
LinkedIn
Email Thirteen new 3‐acetyl‐2,5‐disubstituted‐1,3,4‐oxadiazoline derivatives were synthesized from corresponding hydrazide‐hydrazones of isonicotinic acid in the reaction with acetic anhydride. The obtained compounds were identified with the use of spectral methods (IR, 1H‐NMR, 13C‐NMR, MS). In vitro antimicrobial activity screening of synthesized compounds against a panel of bacteria and fungi revealed interesting antibacterial and antifungal activity of tested 1,3,4‐oxadiazoline derivatives, which is comparable to that of commonly used antimicrobial agents.
This paper references
Synthesis of 1- (4-phenoxyphenyl)-3-[5-(substituted aryl)-1,3,4-oxadiazol-2yl]propan-1-ones as safer anti-inflammatory and analgesic agents
A. Husain (2008)
10.1016/j.jsps.2017.05.006
Synthesis and investigation of antimicrobial activities of nitrofurazone analogues containing hydrazide-hydrazone moiety
Łukasz Popiołek (2017)
Synthesis of novel 3-(4-acetyl-5H/methyl-5-substituted phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-2H-chromen-2-ones as potential anticonvulsant agents.
M. A. Bhat (2008)
10.1515/znc-2009-11-1203
Anti-HIV Activity of New Substituted 1,3,4-Oxadiazole Derivatives and their Acyclic Nucleoside Analogues
W. A. El-Sayed (2009)
Biernasiuk, ‘Hydrazide-hydrazones of 3methoxybenzoic acid and 4-tert-butylbenzoic acid with promising antibacterial activity against Bacillus spp
A.Ł. Popiołek (2016)
10.1111/cbdd.12820
Design, synthesis, and in vitro antimicrobial activity of hydrazide–hydrazones of 2‐substituted acetic acid
Łukasz Popiołek (2016)
10.1111/cbdd.13158
New hydrazide–hydrazones of isonicotinic acid: synthesis, lipophilicity and in vitro antimicrobial screening
Łukasz Popiołek (2018)
10.1155/2009/698023
Syntheses, Evaluation and Characterization of Some 1, 3, 4-Oxadiazoles as Antimicrobial Agents
Niti Bhardwaj (2009)
10.1155/2015/637652
New 1,3,4-Oxadiazole Based Photosensitizers for Dye Sensitized Solar Cells (DSSCs)
U. Mehmood (2015)
10.1016/J.APSUSC.2016.07.115
Corrosion inhibition performance of 2,5-bis(4-dimethylaminophenyl)-1,3,4-oxadiazole for carbon steel in HCl solution: Gravimetric, electrochemical and XPS studies
M. Bouanis (2016)
Reference method for broth dilution antifungal susceptibility testing of yeasts : Approved standard
J. Rex (2008)
10.1080/02678291003632637
Bent-shaped mesogenic oxadiazole and thiadiazole derivatives from rod-shaped mesogenic hydrazide containing polar chloro group
A. K. Prajapati (2010)
10.3109/14756366.2016.1170012
Hydrazide-hydrazones of 3-methoxybenzoic acid and 4-tert-butylbenzoic acid with promising antibacterial activity against Bacillus spp
Łukasz Popiołek (2016)
New 1,3,4-Oxadiazole Based Photosensitizers for Dye Sensitized Solar Cells
U. Mehmood (2015)
10.1039/C6TC05659H
Novel benzo[c][1,2,5]oxadiazole-naphthalenediimide based copolymer for high-performance air-stable n-type field-effect transistors exhibiting high electron mobility of 2.43 cm2 V−1 s−1
Z. Zhao (2017)
10.1016/S0040-4020(01)85962-7
The synthesis of antihypertensive 3-(1,3,4-oxadiazol-2-yl)phenoxypropanolahines
R. Schlecker (1988)
10.1016/j.bmc.2008.05.054
Development of novel beta-amyloid probes based on 3,5-diphenyl-1,2,4-oxadiazole.
M. Ono (2008)
10.1021/JM0004087
Design and synthesis of new orally active nonpeptidic inhibitors of human neutrophil elastase.
K. Ohmoto (2000)
Synthesis and antitumor evaluation of some new 1,3,4-oxadiazolebased heterocycles
S. Bondock (2012)
10.1002/CHIN.200548144
Synthesis and anticancer activity studies on some 2-chloro-1,4-bis-(5-substituted- 1,3,4-oxadiazol-2-ylmethyleneoxy) phenylene derivatives
B. S. Holla (2005)
10.1016/J.BMCL.2007.10.092
Discovery of amide and heteroaryl isosteres as carbamate replacements in a series of orally active gamma-secretase inhibitors.
Mark D. McBriar (2008)
Determination of minimum inhibitory concentrations (MICS) of antibacterial agents by broth dilution
(2003)
10.1007/s40242-016-6029-2
Design, synthesis and herbicidal activity of novel sulfonylureas containing triazole and oxadiazole moieties
Dongkai Zhang (2016)
10.1039/C6TC02924H
Self-assembly and mechanochromic luminescence switching of trifluoromethyl substituted 1,3,4-oxadiazole derivatives
Rahul M. Ongungal (2016)
10.1039/C7TC02767B
Tuning of luminescence color of π-conjugated liquid crystals through co-assembly with ionic liquids
Masato Mitani (2017)
10.1002/cbdv.201700075
New Hydrazides and Hydrazide‐Hydrazones of 2,3‐Dihalogen Substituted Propionic Acids: Synthesis and in vitro Antimicrobial Activity Evaluation
Łukasz Popiołek (2017)
10.7164/antibiotics.24.443
In vitro sensitivity of mycoplasmas isolated from various animals and sewage to antibiotics and nitrofurans.
M. Ogata (1971)
Development of novel β-amyloid probes based on 3,5-diphenyl-1,2,4oxadiazole
M. Ono (2008)
Synthesis of certain 1,3,4-oxadiazole derivatives as potential anticonvulsant', Ind
O M Nassar (1997)
10.2903/j.efsa.2017.4872
ECDC/EFSA/EMA second joint report on the integrated analysis of the consumption of antimicrobial agents and occurrence of antimicrobial resistance in bacteria from humans and food‐producing animals
O. Heuer (2017)
10.1016/J.ARABJC.2011.11.009
Synthesis, characterization and antimicrobial activity of benzodioxane ring containing 1,3,4-oxadiazole derivatives
H. Khalilullah (2016)
10.1039/C4TC02348J
A high triplet energy, high thermal stability oxadiazole derivative as the electron transporter for highly efficient red, green and blue phosphorescent OLEDs
C. Shih (2015)
10.1128/MMBR.00016-10
Origins and Evolution of Antibiotic Resistance
J. Davies (2010)
Synthesis, characterization and antimicrobial activity of benzodioxane ring containing 1,3,4-oxadiazole derivatives’, Arab
H. Habibullah (2019)
Origins and Evolution of Antibiotic Resistance', Microbiol
J Davies (2010)
10.1002/CHIN.201006125
Synthesis and Evaluation of Some Novel Substituted 1,3,4‐Oxadiazole and Pyrazole Derivatives for Antitubercular Activity.
Shashikant R. Pattan (2009)
10.1134/S2070205117020228
A simple approach for assessment of the corrosion inhibition efficiency of triazole, oxadiazole and thiadiazole derivatives as a function of their concentrations without using complex computer codes
Zeinab Shirazi (2017)
10.1080/02678292.2010.535659
Mesogenic bent-shaped nitrooxadiazoles and thiadiazoles
A. K. Prajapati (2011)
10.1016/j.biopha.2018.04.163
New hydrazide-hydrazones and 1,3-thiazolidin-4-ones with 3-hydroxy-2-naphthoic moiety: Synthesis, in vitro and in vivo studies.
Łukasz Popiołek (2018)
10.1016/J.JCT.2018.04.003
Solvation thermodynamics of anti-tuberculosis Isoniazid in aqueous and in aqueous electrolytic media
Latha Malladi (2018)
10.1002/CHIN.200728034
Synthesis, Antimicrobial, and Antiinflammatory Activities of Novel 2-(1-Adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-Adamantylamino)-5-substituted-1,3,4-thiadiazoles.
A. Kadi (2007)
10.1016/j.bioorg.2018.01.020
Synthesis, biological evaluation and molecular modeling studies of phenyl-/benzhydrylpiperazine derivatives as potential MAO inhibitors.
B. Kumar (2018)
10.1016/J.ARABJC.2011.05.004
Conventional and microwave techniques for the synthesis and antimicrobial studies of novel 1-[2-(2-chloro-6-methyl(3-quinolyl))-5-(4-nitrophenyl)-(1,3,4-oxadiazolin-3-yl)]-3-(aryl)prop-2-en-1-ones
N. Desai (2016)
Evaluation of Antibacterial and Antifungal Activity of some 1, 3, 4 Oxadiazoles
P. Sengupta (2008)
10.2298/JSC0809781H
Synthesis of 1-(4-phenoxyphenyl)-3-(5-(substituted aryl)-1,3,4-oxadiazol-2-yl)propan-1-ones as safer anti-inflammatory and analgesic agents
A. Husain (2008)
10.1080/01411594.2010.505341
Bent-shaped mesogenic oxadiazoles and thiadiazoles with terminal methyl group
A. K. Prajapati (2010)
10.1155/2014/172791
1,3,4-Oxadiazole Derivatives: Synthesis, Characterization, Antimicrobial Potential, and Computational Studies
S. Bala (2014)
10.1016/j.ejmech.2011.12.013
Synthesis and antitumor evaluation of some new 1,3,4-oxadiazole-based heterocycles.
S. Bondock (2012)
10.1039/c4cc08649j
Synthesis of nanoporous 1,2,4-oxadiazole networks with high CO2 capture capacity.
Dongah Ko (2015)
Evaluation of antibacterial and antifungal activity of some 1,3,4-oxadiazoles’, Iran
P. Sengupta (2008)
Wujec, ‘New hydrazide-hydrazones and 1,3thiazolidin-4-ones with 3-hydroxy-2-naphthoic moiety: Synthesis, in vitro and in vivo studies
Ł. Popiołek (2018)
10.1021/CR950066Q
Bioisosterism: A Rational Approach in Drug Design.
George A. Patani (1996)
10.1016/j.ejmech.2017.12.067
Synthesis and antimicrobial activity of pyrimidinyl 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles.
M. Madhu Sekhar (2018)
10.1016/j.carres.2011.03.004
Synthesis of variously coupled conjugates of D-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase.
Sándor Kun (2011)
10.1590/S0103-50532010000200014
Synthesis, antitumor and antimicrobial activity of novel 1-substituted phenyl-3-[3-alkylamino(methyl)-2-thioxo-1,3,4-oxadiazol-5-yl] β-carboline derivatives
F. C. Savariz (2010)
10.5923/J.AJOC.20160602.02
Design, Synthesis, and Biological Evaluation of Novel 5-Substituted-2-(3,4,5-trihydroxyphenyl)-1,3,4-oxadiazoles as Potent Antioxidants
A. M. Rabie (2016)
10.1016/J.ARABJC.2013.12.020
Synthesis and biological evaluation of newer analogues of 2,5-disubstituted 1,3,4-oxadiazole containing pyrazole moiety as antimicrobial agents
S. Malladi (2014)
10.1016/J.MOLSTRUC.2014.01.084
Synthesis and structure of new mononuclear octahedral cobalt(III) dioximates derived from isonicotinic hydrazide
Maria Cocu (2014)
10.1016/J.INOCHE.2016.12.007
A novel 1-D coordination polymer constructed from disilver-1,3,4-oxadiazole nodes and perchlorato bridges
C. Anghel (2017)
10.2165/00003495-200969080-00007
Raltegravir: a review of its use in the management of HIV infection in treatment-experienced patients.
Jamie D. Croxtall (2009)
10.1021/jm00113a009
Comparison of azabicyclic esters and oxadiazoles as ligands for the muscarinic receptor.
B. Orlek (1991)
10.1038/clpt.1983.170
Effects of tiodazosin, a new antihypertensive, hemodynamics and clinical variables
S. Vardan (1983)
10.1007/s11051-013-2085-4
White light-emitting nanocomposites based on an oxadiazole–carbazole copolymer (POC) and InP/ZnS quantum dots
A. Bruno (2013)
10.1016/j.bmcl.2008.10.015
2-Alkylamino- and alkoxy-substituted 2-amino-1,3,4-oxadiazoles-O-Alkyl benzohydroxamate esters replacements retain the desired inhibition and selectivity against MEK (MAP ERK kinase).
J. Warmus (2008)
10.1016/J.EJMECH.2006.10.003
Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles.
A. Kadi (2007)
Synthesis of certain 1,3,4-oxadiazole derivatives as potential anticonvulsant
O. M. Nassar (1997)
Synthesis and investigation of antimicrobial activities of nitrofurazone analogues containing hydrazide-hydrazone moiety', Saudi Pharm
Ł Popiołek (2017)
This paper is referenced by
Some data provided by SemanticScholar