Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

Gauthier, Marie-Pierre; Michaux, Catherine; Rolin, Stéphanie; Vastersaegher, Caroline; Leval, Xavier de; Julémont, Fabien; Pochet, Lionel; Masereel, Bernard

doi:10.1016/j.bmc.2005.09.005

Cited by 14 publications

(12 citation statements)

References 39 publications

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“…Imidazoles are reported to have broad biological activities [ 1 , 2 , 3 , 4 ]. On the other hand, over the past two decades; pyrazole-containing compounds have received considerable attention owing to their diverse chemotherapeutic potential, including antineoplastic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives

Gomha

Hassaneen

2011

Molecules

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A novel series of 7,7-diphenyl-1,2-dihydroimidazo[2,1-c][1,2,4]triazin-6(7H)-one 6a–h, were easily prepared via reactions of novel 2-hydrazinyl-4,4-diphenyl-1H-imidazol-5(4H)-one (2) with hydrazonoyl halides 3a–h. In addition, we also examined the reaction of compound 2 with commercially available active methylene compounds to afford new pyrazoles containing an imidazolone moiety, expected to be biologically active. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1H-NMR and mass spectral data. The antifungal and antibacterial activities of the newly synthesized compounds were evaluated.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives

Gomha

Hassaneen

2011

Molecules

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“…These analyses identified some differences in the residues that may affect the site selectivity of specific compounds to either isoform [38,39]. In particular, several residues, including Try355 and Arg120 (Figure 3A), allow the formation of hydrogen bonds, which favor interactions with COX-1 inhibitors [40,41]. One of the most widely reported difference is a change between isoleucine (COX-1) to valine (COX-2) at positions 434 and 523, respectively (Figure 3A).…”

Section: Resultsmentioning

confidence: 99%

Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit

Melo

Chelucci

Pires

et al. 2014

IJMS

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A series of anti-inflammatory derivatives containing an N-acyl hydrazone subunit (4a–e) were synthesized and characterized. Docking studies were performed that suggest that compounds 4a–e bind to cyclooxygenase (COX)-1 and COX-2 isoforms, but with higher affinity for COX-2. The compounds display similar anti-inflammatory activities in vivo, although compound 4c is the most effective compound for inhibiting rat paw edema, with a reduction in the extent of inflammation of 35.9% and 52.8% at 2 and 4 h, respectively. The anti-inflammatory activity of N-acyl hydrazone derivatives was inferior to their respective parent drugs, except for compound 4c after 5 h. Ulcerogenic studies revealed that compounds 4a–e are less gastrotoxic than the respective parent drug. Compounds 4b–e demonstrated mucosal damage comparable to celecoxib. The in vivo analgesic activities of the compounds are higher than the respective parent drug for compounds 4a–b and 4d–e. Compound 4a was more active than dipyrone in reducing acetic-acid-induced abdominal constrictions. Our results indicate that compounds 4a–e are anti-inflammatory and analgesic compounds with reduced gastrotoxicity compared to their respective parent non-steroidal anti-inflammatory drugs.

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“…[13] In order to improve the efficiency of PTH-amino-acid synthesis, several attempts have been carried out and encouraging results were obtained. The reaction has been conducted with amino acid in the presence of KOH/EtOH [14] , Na 2 CO 3 /Dioxane [15] , KOH/EtOH/AcOH [16] , Ionic liquid [17] , NaOH/water/acetone [18] , NaOH/EtOH/HCl [19] and NaOH/H 2 O/HCl [20] , Pyridine/NaOH H 2 O/HCl [21] , Et 3 N/dioxane/H 2 O/HCl [22] , reflux at higher temperature [23a] , Ethyl thiophosphate [23b] and aldehyde with thiourea in phosphoric acid [23c] , Benzyl with thiourea in NaOH/EtOH [24a, 24b] , DMF-K 2 CO 3 and KOH/DMSO. [25] Whereas with amino acid esters in the presence of CH 2 Cl 2 /Et 3 N [10,26] , Aqueous pyridine/Et 3 N/Dioxane [27] , KOH/H 2 O/HCl [28] , NaHCO 3 /EtOH/HCl [29] , AcOH/HCl [30] , …”

Section: Introductionmentioning

confidence: 99%

Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives fromS-Amino Acids and Phenylisothiocyanate in Et₃N/DMF-H₂O

Jangale

Wagh

Tayade

et al. 2015

Synthetic Communications

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Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

Cited by 14 publications

References 39 publications

Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives

Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives

Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit

Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives fromS-Amino Acids and Phenylisothiocyanate in Et₃N/DMF-H₂O

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Synthesis, molecular modelling and enzymatic evaluation of (±)3,5-diphenyl-2-thioxoimidazolidin-4-ones as new potential cyclooxygenase inhibitors

Cited by 14 publications

References 39 publications

Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives

Synthesis and Antimicrobial Activity of Some New Pyrazoles, Fused Pyrazolo[3,4-d]-pyrimidine and 1,2-Dihydroimidazo-[2,1-c][1,2,4]triazin-6-one Derivatives

Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit

Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives fromS-Amino Acids and Phenylisothiocyanate in Et3N/DMF-H2O

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Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives fromS-Amino Acids and Phenylisothiocyanate in Et₃N/DMF-H₂O