Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs

Yadav, Pawan Kumar; Singh, Praveen; Tewari, Ashish Kumar

doi:10.1016/j.bmcl.2014.03.087

Cited by 74 publications

(29 citation statements)

References 29 publications

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“…Study of protein–protein or protein-receptor interactions through in silico analysis has been proved to be an efficient tool for drug designing. Similar study conducted that revealed benzofuran having high affinity for active site of COX-2 receptor showing it to be a good anti-inflammatory compound (Yadav et al 2014 ). Molecular docking of several compounds was performed by Valasani et al ( 2014 ) for a potential inhibitor for cyclophilin D, a crucial mitochondrial membrane protein.…”

Section: Discussionmentioning

confidence: 67%

Antimicrobial action of methanolic seed extracts of Syzygium cumini Linn. on Bacillus subtilis

et al. 2017

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Phytochemicals of Syzygium cumini are used for the treatment of various diseases as a traditional medicine but the mechanism behind their action is not well reported. Antimicrobial activity of methanolic seed extract of S. cumini was done by agar well diffusion assay on Bacillus subtilis and its zone of inhibition was found to be 20.06 mm in comparison to control having no zone of inhibition. MIC of S. cumini was found to be 0.3 mg/ml. Genomic DNA degradation of B. subtilis reveals apoptosis and FE-scanning electron microscope indicates cell wall cracking on several intervals of time. Results of propidium iodide staining showed few bacterial cells were stained in control; however population of stained cells increased after exposing them for varying period of time. Flow cytometric kinetic data analysis on the membrane permeabilization in bacterial cell showed the significant contribution of antimicrobial potential of the seed extract on antimicrobial-induced permeabilization. In silico analysis revealed two components of S. cumini methanolic extract to be active against four enzymes (PDB ID—1W5D, 4OX3, 3MFD and 5E2F) which are crucial for plasma membrane synthesis in B. subtilis. Moreover lupeol showed highest binding energy for macromolecule 1W5D and 4OX3 forming one hydrogen bond each whereas stigmasterol showed the highest binding energy for macromolecule 3MFD and 5E2F forming four hydrogen bonds and alkyl bonds respectively. It demonstrates that methanolic seed extracts of S. cumini could be used for inhibition of food born infection caused by B. subtilis and also an alternative of prevalent antibiotics.

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Section: Discussionmentioning

confidence: 67%

Antimicrobial action of methanolic seed extracts of Syzygium cumini Linn. on Bacillus subtilis

et al. 2017

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“…Furan is one of the most prominent five‐membered heterocycles and has been extensively studied owing to its widespread occurrence in many natural products, pharmaceuticals, and functional materials . Compounds featuring a furan skeleton exhibit diverse biological properties, such as anticancer, anti‐inflammatory, antiallergic, hair‐growth‐stimulating and immunosuppressive activities (Figure ) . In addition, they are also useful building blocks in organic synthesis…”

Section: Figurementioning

confidence: 99%

Paal–Knorr Furan Synthesis Using TiCl₄ as Dehydrating Agent: A Concise Furan Synthesis from α‐Haloketones and β‐Dicarbonyl Compounds

Luo

Lü

et al. 2017

Asian J Org Chem

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An efficient andf acile methodf or the Paal-Knorr furan synthesis using titaniumt etrachloride as dehydrating agenti sd escribed. Tricarbonyl compounds, prepared through the nucleophilic substitution of a-halogenated ketones and b-dicarbonyl compounds, are easily condensed to their corresponding polysubstituted furans. The reaction also occurs efficiently with tetracarbonyl compounds derived by dimerization of b-dicarbonyl compounds.

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“…Benzofuran and its analogues are important core structures for drug discovery, showing excellent pharmacological activity like antiviral [13], anticancer [14], anti-inflammatory [15], antihyperlipidemic [16], anti-Alzheimer’s [17], anticonvulsant [18], antitubercular [19], CNS regulatory [20], analgesic [21], enzyme inhibition [22,23], antipyretic activities [24].…”

Section: Introductionmentioning

confidence: 99%

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

et al. 2019

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Inhibition of α-amylase and α-glucosidase by specified synthetic compounds during the digestion of starch helps control post-prandial hyperglycemia and could represent a potential therapy for type II diabetes mellitus. A new series of spiroheterocyclic compounds bearing oxindole/benzofuran/pyrrolidine/thiazolidine motifs were synthesized via a 1,3-dipolar cyclo-addition reaction approach. The specific compounds were obtained by reactions of chalcones having a benzo[b]furan scaffold (compounds 2a–f), with a substituted isatin (compounds 3a–c) and heterocyclic amino acids (compounds 4a,b). The target spiroindolone analogues 5a–r were evaluated for their potential inhibitory activities against the enzymes α-amylase and α-glucosidase. Preliminary results indicated that some of the target compounds exhibit promising α-amylase and α-glucosidase inhibitory activity. Among the tested spiroindolone analogues, the cycloadduct 5r was found to be the most active (IC50 = 22.61 ± 0.54 μM and 14.05 ± 1.03 μM) as α-amylase and α-glucosidase inhibitors, with selectivity indexes of 0.62 and 1.60, respectively. Docking studies were carried out to confirm the binding interaction between the enzyme active site and the spiroindolone analogues.

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Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs

Cited by 74 publications

References 29 publications

Antimicrobial action of methanolic seed extracts of Syzygium cumini Linn. on Bacillus subtilis

Antimicrobial action of methanolic seed extracts of Syzygium cumini Linn. on Bacillus subtilis

Paal–Knorr Furan Synthesis Using TiCl₄ as Dehydrating Agent: A Concise Furan Synthesis from α‐Haloketones and β‐Dicarbonyl Compounds

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

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Design, synthesis, docking and anti-inflammatory evaluation of novel series of benzofuran based prodrugs

Cited by 74 publications

References 29 publications

Antimicrobial action of methanolic seed extracts of Syzygium cumini Linn. on Bacillus subtilis

Antimicrobial action of methanolic seed extracts of Syzygium cumini Linn. on Bacillus subtilis

Paal–Knorr Furan Synthesis Using TiCl4 as Dehydrating Agent: A Concise Furan Synthesis from α‐Haloketones and β‐Dicarbonyl Compounds

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

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Paal–Knorr Furan Synthesis Using TiCl₄ as Dehydrating Agent: A Concise Furan Synthesis from α‐Haloketones and β‐Dicarbonyl Compounds