Sulfonamide Derivatives of 2-Amino-1-phenylethane as Suitable Cholinesterase Inhibitors

Abbasi, MA; Ahmad, Shabir; Rehman, Azizur; Rasool, Shahid; Khan, KM; Ashraf, Muhammad; Nasar, Rumana; Ismail, Tayaba

doi:10.4314/tjpr.v13i5.13

Cited by 11 publications

(6 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The compounds with sulfamoyl moiety have been introduced as valuable biologically active compounds and in accordance with our previous findings [13][14][15][16], the overview of synthesized compounds hereby showed that N-substitution of sulfamoyl group with aliphatic chains and halogenated aromatic compounds presented best activity because of best fit to active site of enzyme and better π-π interactions. The two molecules, 5g and 5j, showed good activity against α-glucosidase probably because of branched long alkyl chain in 5g and p-substituted halogenated aralkyl group in 5j, presented better binding interactions with the active site of enzyme.…”

Section: Discussionsupporting

confidence: 85%

“…The hemolysis takes place due to the stroke of the microbial products and resident parasites on the red blood corpuscles membranes [11,12]. Our group has synthesized many antibacterial and anti-enzymatic potent molecules [13][14][15][16] and a series of new compounds was synthesized in the present study to explore their pharmacological behavior.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Abbasi¹,

Islam²,

Rehman³

et al. 2016

Trop. J. Pharm Res

View full text Add to dashboard Cite

show abstract

Section: Discussionsupporting

confidence: 85%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Abbasi¹,

Islam²,

Rehman³

et al. 2016

Trop. J. Pharm Res

View full text Add to dashboard Cite

show abstract

“…Therefore, it is important to search new cholinesterase inhibitors as possible drug candidates ( Colovic et al, 2013 ; Grieg et al, 2014 ). In our previous attempts, we have reported some sulfonamides as acetylcholinesterase inhibitors and these molecules were having either no substituent or an ethoxy along with halogen substituents in the starting amine ( Abbasi et al, 2014a ; Abbasi et al, 2014b ). In the present investigation, we synthesized a new series of sulfonamides starting from an amine (4-methoxyphenethy amine) bearing an electron donating methoxy group at 4-position in its structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, enzyme inhibitory kinetics mechanism and computational study ofN-(4-methoxyphenethyl)-N-(substituted)-4-methylbenzenesulfonamides as novel therapeutic agents for Alzheimer’s disease

Abbasi

Hassan

Aziz-Ur-Rehman

et al. 2018

PeerJ

View full text Add to dashboard Cite

The present study comprises the synthesis of a new series of sulfonamides derived from 4-methoxyphenethylamine (1). The synthesis was initiated by the reaction of 1 with 4-methylbenzenesulfonyl chloride (2) in aqueous sodium carbonate solution at pH 9 to yield N-(4-methoxyphenethyl)-4-methylbenzensulfonamide (3).This parent molecule 3 was subsequently treated with various alkyl/aralkyl halides, (4a–j), using N,N-dimethylformamide (DMF) as solvent and LiH as activator to produce a series of new N-(4-methoxyphenethyl)-N-(substituted)-4-methylbenzenesulfonamides (5a–j). The structural characterization of these derivatives was carried out by spectroscopic techniques like IR, 1H-NMR, and 13C-NMR. The elemental analysis data was also coherent with spectral data of these molecules. The inhibitory effects on acetylcholinesterase and DPPH were evaluated and it was observed that N-(4-Methoxyphenethyl)-4-methyl-N-(2-propyl)benzensulfonamide (5c) showed acetylcholinesterase inhibitory activity 0.075 ± 0.001 (IC50 0.075 ± 0.001 µM) comparable to Neostigmine methylsulfate (IC50 2.038 ± 0.039 µM).The docking studies of synthesized ligands 5a–j were also carried out against acetylcholinesterase (PDBID 4PQE) to compare the binding affinities with IC50 values. The kinetic mechanism analyzed by Lineweaver-Burk plots demonstrated that compound (5c) inhibits the acetylcholinesterase competitively to form an enzyme inhibitor complex. The inhibition constants Ki calculated from Dixon plots for compound (5c) is 2.5 µM. It was also found from kinetic analysis that derivative 5c irreversible enzyme inhibitor complex. It is proposed on the basis of our investigation that title compound 5c may serve as lead structure for the design of more potent acetylcholinesterase inhibitors.

show abstract

“…Tal composto foi adotado como modelo para a série de compostos sintetizados neste presente trabalho (BHATTACHARJEE et al, 2015;ABBASI et al, 2014).…”

Section: Introductionunclassified

Sinergismo in Vitro Da Associação Entre Pralidoxima E Sulfonamidas Na Reativação Da Acetilcolinesterase Humana Recombinante Inibida Por Paraoxon

Garcia¹

2017

Acta Biomed.Bras.

View full text Add to dashboard Cite

Foi realizada a avaliação da capacidade de reativação da acetilcolinesterase humana recombinante inibida previamente com solução de Paraoxon 2 µM diante de pralidoxima em solução a 100 µM em associação com onze derivados de sulfonamida em solução a 100 µM em dimetilsulfóxido, a saber, N-(2-clorofenil)benzenossulfonamida, N-(4-fluorofenil)benzenossulfonamida, N-(4-fluorofenil)-4-nitrobenzenossulfonamida, 4-cloro-N-(4-fluorofenil)benzenossulfonamida, N-(3-clorofenil)benzenossulfonamida, N-(3-cloro-2-metilfenil)benzenossulfonamida, 4-cloro-N-fenilbenzenossulfonamida, N-(2-clorofenil)-4-metilbenzenossulfonamida, N-(3-clorofenil)-4-metilbenzenossulfonamida, N-(2-hidroxietil)-4-metil-N-fenilbenzenossulfonamida e /N-(4-nitrofenil)benzenossulfonamida. É a primeira vez que estes derivados de sulfonamida são apresentados em associação com a pralidoxima como potenciais agentes terapêuticos para o tratamento da intoxicação por compostos organofosforados. Todas as associações avaliadas demonstraram capacidade de reativar a acetilcolinesterase humana recombinante previamente inibida por paraoxon nas doses avaliadas. As moléculas com maior potencial de reativação da atividade da acetilcolinesterase em associação com a pralidoxima foram N-(2-clorofenil)benzenossulfonamida e N-(4-fluorofenil)benzenossulfonamida.

show abstract

Sulfonamide Derivatives of 2-Amino-1-phenylethane as Suitable Cholinesterase Inhibitors

Cited by 11 publications

References 12 publications

Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

Synthesis, enzyme inhibitory kinetics mechanism and computational study ofN-(4-methoxyphenethyl)-N-(substituted)-4-methylbenzenesulfonamides as novel therapeutic agents for Alzheimer’s disease

Sinergismo in Vitro Da Associação Entre Pralidoxima E Sulfonamidas Na Reativação Da Acetilcolinesterase Humana Recombinante Inibida Por Paraoxon

Contact Info

Product

Resources

About