Synthesis, Urease Inhibition, Antioxidant, Antibacterial, and Molecular Docking Studies of 1,3,4-Oxadiazole Derivatives

Hanif, Muhammad; Shoaib, Khurram; Saleem, M.; Rama, Nasim Hasan; Zaib, Sumera; Iqbal, Jamshed

doi:10.5402/2012/928901

Cited by 51 publications

(39 citation statements)

References 30 publications

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“…The J values of the analyzed compounds are presented in Hertz (Hz). The spectra of 13 C -NMR were recorded at a frequency of 75.5 MHz or 125 MHz. EIMS spectra were obtained using Agilent TOF-6220 analyzer, while the elements were analyzed on a Perkin Elmer 2400 CHN instrument.…”

Section: Experimental Analytical Proceduresmentioning

confidence: 99%

“…In this regard, high throughput virtual and in vitro biological assay of molecules to understand their molecular behaviour in specific environments, will aid the identification of potent molecules from a crude cocktail [12]. Recently, 1,3,4-oxadiazole-2-thiones derivatives have been investigated as active jack bean urease inhibitors with promising anti-urease activities [13]. The aim of the current study was to synthesize Mannich bases derived from 1, 3, 4-oxadiazole-2-thione bearing 3, 4, 5-trimethoxy moiety and examine them as potential urease inhibitors and antioxidant agents.…”

Section: Introductionmentioning

confidence: 99%

“…

Abstract Purpose: To design and synthesize a series of new structural motifs of urease inhibitors, 3-[{(substituted phenyl) amino} methyl]-5-(3, 4, 5-trimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thiones and 3-{[(pyridin-2-yl)amino]methyl}- 5-(3,4,5-trimethoxy phenyl)-1,3,4-oxadiazole-2(3H) 4,5,9,10,12,13, values in the range of 5. 93 ± 0.13 to 9.76 ± 0.11,

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confidence: 99%

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Synthesis, biological evaluation and molecular docking studies of Mannich bases derived from 1, 3, 4-oxadiazole- 2-thiones as potential urease inhibitors

Akram¹,

Saeed²,

ahmed³

et al. 2018

Trop. J. Pharm Res

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Section: Experimental Analytical Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, biological evaluation and molecular docking studies of Mannich bases derived from 1, 3, 4-oxadiazole- 2-thiones as potential urease inhibitors

Akram¹,

Saeed²,

ahmed³

et al. 2018

Trop. J. Pharm Res

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“…In reality more effective and potent compounds are mandatory with a complete new level of safety and specificity. Urease inhibitors for this purpose have gained incredible attention in recent times and therefore resulted into the discovery of numerous inhibitors [8,[10][11][12][13].…”

Section: Editorialmentioning

confidence: 99%

Patho-Phyisology of Urease: Urease Inhibiters as a Significant Therapeutic Goal

Khan¹

2015

Biol Med (Aligarh)

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EditorialUrease (urea amidohydrolase) is usually found in different bacteria, fungi, algae and plants. It is accountable for the hydrolysis of urea and thus, forming ammonia and carbamate, which is the final step of nitrogen metabolism in living organisms [1,2]. The carbamate intern quickly and spontaneously decomposes, yielding a second molecule of ammonia. These reactions may cause significant increase in pH and are therefore, responsible for negative effects of urease activity in human health and agriculture [3,4].The experimental findings suggested that infections produced by bacteria such as Helicobacter pylori and Proteus mirabilis usually have a high urease activity. Urease is central toH. pylorimetabolism and virulence, necessary for its colonization in gastric mucosa [5,6]. It is a potent immunogen that elicits a strong immune response. Urease represents an interesting model for metalloenzyme studies. Before the discovery ofH. pylori, urease production was limited to human physiology. But now the contribution of this bacterium in urease production is well established. It contributes in urinary tract and gastrointestinal infections, probably augmenting the severity of several pathological conditions like peptic ulcers and stomach cancer etc. Ureases are also involved in the development of different human and animal pathogenicity such as urolithiasis, pyelonephritis, hepatic encephalopathy, hepatic coma and urinary catheter encrustation [7][8][9]. Over urease production is also contributing in environmental hazards.The enzyme has been recognized that it is one of the key agents in the pathophysiology of multiple human and animal disorders, targeting urease for treating pathogenic disorders caused by ureaseproducing-bacteria has already open a new line of treatment for infections caused by such bacteria. In reality more effective and potent compounds are mandatory with a complete new level of safety and specificity. Urease inhibitors for this purpose have gained incredible attention in recent times and therefore resulted into the discovery of numerous inhibitors [8,[10][11][12][13].To summarize, urease inhibitors are highly potential target for different pathological conditions induced urease hyperactivity. References

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“…These inhibitors generally divided into two classes, substrate structural analogs like hydroxamic acid (Kobashi K 1962,;Krajewska B 2009;Muri EMF 2003) and those which affect the mechanism of the reaction like phosphoramidat (Amtul Z 2002;Kot M 2001). Lansoprazole (Nagata K 1993), omeprazole (Kuehler TC 1995), thiol-compounds (Todd MJ 1989), quinines (Bundy LG 1973) and schiff base derivatives (Hanif M 2012) are reported as potent urease inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Urease Inhibition Studies of Transition Metal Complexes of Thioureas Bearing Ibuprofen Moiety

Mumtaz

Arshad

Saeed

et al. 2018

J. Chil. Chem. Soc.

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Starting from ibuprofen, a non-steroidal anti-inflammatory drug, N,N'-disubstituted thiourea derivatives were synthesized by refluxing the acid chloride of ibuprofen with potassium thiocyanate followed by substituted anilines to get N-2- (4-(2-methylpropyl) phenyl)propionoyl-N´-(2´-bromophenyl) thiourea (1), N-2-(4-(2-methylpropyl)phenyl)propionoyl-N´-(2´-chlorophenyl) thiourea (2) and N-2-(4-(2-methylpropyl)phenyl)propionoyl-N´-(3´,4´-dichlorophenyl) thiourea (3).Metal complexes (4-15) of (1-3) were synthesized by refluxing it with one equivalence salts of Co (ΙΙ), Ni(ΙΙ), Pb(ΙΙ) and Cu(Ι). Structures of all the synthesized thiourea ligands and their metal complexes were determined by FTIR and 1 HNMR spectroscopy. Shift in stretching frequency in FTIR and resonance frequency in 1 HNMR spectroscopic data suggested that the ligands and metal are coordinated to afford respective metal complexes M[L] n . The synthesized compounds were tested against urease enzyme and the results were compared with standard thiourea, as positive control. Most of the investigated compounds showed potential inhibitory activity against Jack bean urease. Compound 5 was found to be the most potent urease inhibitor with IC 50 of 14.6 µM, whereas compounds 8, 11 and 12 possessed potent urease inhibition. The tested compounds can be taken as lead molecules for gastrointestinal ulcer therapy.Key words: Amides, Thioureas, Metal complexes, Ibuprofen, Urease. INTRODUCTIONUrease (urea aminohydrolase E.C. 3.5.1.5) is nickel containing metalloenzyme which belongs to the super family of amidohydrolases and phosphotriestreases, responsible for the hydrolytic decomposition of urea (Holm 1997). It was the first enzyme which crystallized from the plant source Canavalia ensiformis and was also the first protein containing nickel in the active site (Saeed et al. 2014;Saeed et al. 2013). Because of these characteristics urease is considered as a paradigm in the development of inorganic biochemistry. Urease catalyses the hydrolysis of urea in different plants, algae, fungi, and microorganisms to produce ammonia and carbamate (Mobley HL 1989). Enzyme catalysed hydrolysis-process occurred at a rate of approximately 10 14 times the rate of the unanalyzed reaction and considered as the final step of nitrogen metabolism in all living organisms. Different types of urease enzymes can be isolated from bacteria, fungi, algae and plants but enzymatic activity is same due to the occarance of the same order of amino acid (Bacanamwo M 2002;Benini S 1999). Urease activity due to infectious microorganism is the major reason for many deceases in humans such as development of infection stones, pyelonephritis, stomach and peptic ulcer, urinary catheter encrustation, and hepatic com (Gripenberg-Lerche C 2000; Mobley et al. 1995;Mobley HL 1989). To overcome these diverse types of problems, urease inhibitors have received special attention over the past few years. These inhibitors generally divided into two classes, substrate structural analogs like hydroxamic acid (Ko...

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Synthesis, Urease Inhibition, Antioxidant, Antibacterial, and Molecular Docking Studies of 1,3,4-Oxadiazole Derivatives

Cited by 51 publications

References 30 publications

Synthesis, biological evaluation and molecular docking studies of Mannich bases derived from 1, 3, 4-oxadiazole- 2-thiones as potential urease inhibitors

Synthesis, biological evaluation and molecular docking studies of Mannich bases derived from 1, 3, 4-oxadiazole- 2-thiones as potential urease inhibitors

Patho-Phyisology of Urease: Urease Inhibiters as a Significant Therapeutic Goal

Synthesis, Characterization and Urease Inhibition Studies of Transition Metal Complexes of Thioureas Bearing Ibuprofen Moiety

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