Design, Synthesis and Antiinflammatory Evaluation of 5(6)-(un)-substituted-1H-Benzimidazol-2-ylthioacetylpiperazine Derivatives

Ganji, L. V.; Agrawal, P. Ν.

doi:10.36468/pharmaceutical-sciences.619

Cited by 4 publications

(3 citation statements)

References 16 publications

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“…The membrane-binding domain, which forms the hydrophobic pocket within the COX-2 active site, is lined with aromatic and hydrophobic amino acid residues, including Tyr348, Val349, Phe381, Leu384, Tyr385, Trp387, Met522, Gly526, Ala527, Ser530, and Leu531. The catalytic domain, specifically Val116 and Leu359, plays a significant role in binding nonsteroidal anti-inflammatory drugs (NSAIDs) [54][55][56]. Molecular docking against COX-2 (PDB ID: 4COX) was conducted for SR22, SR24, and SR42, showing promising inhibitory potential.…”

Section: Molecular Docking Of Cyclooxygenase-2 Enzymementioning

confidence: 99%

Potential of Tryptamine Derivatives as Multi-Target Directed Ligands for Alzheimer’s Disease: AChE, MAO-B, and COX-2 as Molecular Targets

Asghar,

Mushtaq,

Ahmed

et al. 2024

Molecules

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Extensive research has been dedicated to develop compounds that can target multiple aspects of Alzheimer’s disease (AD) treatment due to a growing understanding of AD’s complex multifaceted nature and various interconnected pathological pathways. In the present study, a series of biological assays were performed to evaluate the potential of the tryptamine analogues synthesized earlier in our lab as multi-target-directed ligands (MTDLs) for AD. To assess the inhibitory effects of the compounds, various in vitro assays were employed. Three compounds, SR42, SR25, and SR10, displayed significant AChE inhibitory activity, with IC50 values of 0.70 µM, 0.17 µM, and 1.00 µM, respectively. These values superseded the standard drug donepezil (1.96 µM). In the MAO-B inhibition assay, SR42 (IC50 = 43.21 µM) demonstrated superior inhibitory effects as compared to tryptamine and other derivatives. Moreover, SR22 (84.08%), SR24 (79.30%), and SR42 (75.16%) exhibited notable percent inhibition against the COX-2 enzyme at a tested concentration of 100 µM. To gain insights into their binding mode and to validate the biological results, molecular docking studies were conducted. Overall, the results suggest that SR42, a 4,5 nitro-benzoyl derivative of tryptamine, exhibited significant potential as a MTDL and warrants further investigation for the development of anti-Alzheimer agents.

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Section: Molecular Docking Of Cyclooxygenase-2 Enzymementioning

confidence: 99%

Potential of Tryptamine Derivatives as Multi-Target Directed Ligands for Alzheimer’s Disease: AChE, MAO-B, and COX-2 as Molecular Targets

Asghar,

Mushtaq,

Ahmed

et al. 2024

Molecules

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“…The synthesized derivatives (at a dose of 150 mg/ Kg) possessed significant anti-inflammatory activity which was almost two-fold greater than diclofenac as depicted in the study. However, thioacetyl piperazine derivatives were found more po- these compounds have good binding interactions with the COX-2 enzyme as compared to others [77]. Synthesis of some new 5-chloro-2(3H)-benzoxazolone derivatives was reported (▶fig.…”

Section: Piperazine Derivatives Possessing Anti-inflammatory and Analmentioning

confidence: 99%

Piperazine: A Promising Scaffold with Analgesic and Anti-inflammatory Potential

et al. 2020

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Piperazine, a nitrogen-containing heterocyclic has acquired an inimitable position in medicinal chemistry because of its versatile structure, which has fascinated researchers to design novel piperazine based molecules having various biological actions. The subsistence of various compounds possessing diverse pharmacological activities in the literature further confirms this fact. Currently available analgesics and anti-inflammatory drugs are associated with side effects that limit their use. Moreover, the literature reveals the incredible anti-inflammatory and analgesic potential of piperazine derivatives along with their method of synthesis, therefore; the present review has been designed to collate the development made in this area that will surely be advantageous in designing novel piperazine based candidates with enhanced efficacy and less toxicity. An extensive literature survey was carried by scrutinizing peer reviewed articles from worldwide scientific databases available on GOOGLE, SCOPUS, PUBMED, and only relevant studies published in English were considered.

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“…Within this family of heterocyclic compounds, benzimidazole derivatives are the most biological actives [4][5][6][7][8][9] interesting as they result from the juxtaposition of benzene and imidazole rings. They have been of particular interest to many researchers given their diverse biological activities including antimicrobial [10][11][12], antiviral [13,14], anticancer [15][16][17], anti-inflammatory [18][19][20], and antioxidant [21]. Benzimidazole derivatives are also proven to be effective proton pump inhibitors [22], stage modulators [23], and antidiabetics [24,25].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives

Coulibaly¹,

COULIBALI²,

Bamba³

et al. 2022

GSC Biol. Pharm. Sci.

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In pursuit the development of novel potent and selective antibacterial agents, we synthesized twelve (12) N-alkyl 2-benzylthiomethyl-1H-benzimidazole derivatives and evaluated their antibacterial activities. Their antibacterial profile was determined with minimal inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) against a small set of two (2) strains Escherichia coli (Gram negative) and Staphylococcus aureus (Gram positive). These compounds are produced by the condensation reaction of 2-benzylthiomethyl-1H-benzimidazole (5) with benzyl chloride or bromide (6) in the presence of potassium carbonate (K2CO3). The panel of twelve synthetized compounds (7a-l) were characterized by NMR 1H, 13C spectroscopy, and high-resolution mass spectrometry (HRMS). The results showed that compounds 7a, 7b, 7c, 7d, 7e, 7f, 7h, 7k, and 7l were potent against Escherichia coli and Staphylococcus aureus, with significant MICs values from 140 to 290 µg/mL. On E. coli, five (5) compounds 7b, 7f, 7i, 7k and 7l showed bactericidal effects within common an N-alkylation by R3= phenyl, methyl, and CH2OH on the benzimidazole scaffold and the benzylthiol substituted by R2= Cl or CF3. This is evidence or a probe of these chemical groups implementing the bactericidal activity.

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Design, Synthesis and Antiinflammatory Evaluation of 5(6)-(un)-substituted-1H-Benzimidazol-2-ylthioacetylpiperazine Derivatives

Cited by 4 publications

References 16 publications

Potential of Tryptamine Derivatives as Multi-Target Directed Ligands for Alzheimer’s Disease: AChE, MAO-B, and COX-2 as Molecular Targets

Potential of Tryptamine Derivatives as Multi-Target Directed Ligands for Alzheimer’s Disease: AChE, MAO-B, and COX-2 as Molecular Targets

Piperazine: A Promising Scaffold with Analgesic and Anti-inflammatory Potential

Synthesis and effect of N-alkylation on antibacterial activity of 2-(Benzylthio) methyl-1H-benzimidazole derivatives

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