Synthesis, pharmacological screening and in silico studies of new class of Diclofenac analogues as a promising anti-inflammatory agents

Palkar, Mahesh B.; Singhai, Anuj S.; Ronad, Pradeepkumar; Vishwanathswamy, A.H.M.; Boreddy, Thippeswamy S.; Veerapur, Veeresh P.; Shaikh, Mahamadhanif S.; Rane, Rajesh A.; Karpoormath, Rajshekhar

doi:10.1016/j.bmc.2014.03.043

Cited by 53 publications

(48 citation statements)

References 42 publications

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“…The key amino acids in the actives site of COX‐1 consist: His90, Arg120, Val349, Tyr355, Arg53, Met522 and Glu524,, where the carboxylic group of ibuprofen formed two hydrogen bonds between NH and NH 2 groups of Arg120 and one hydrogen bond between phenolic OH of Ty355. The main amino acids in the actives site of COX‐2 include: Val349, Ser530, Leu352, Tyr385, Tyr348, Trp387, Gly526, Ala527, Met522, Leu384, His90, Arg120, Tyr355, Arg53, Phe518, and Gly526, where S58 formed four hydrogen bonds with His90, Arg120, Leu352, and Gln192 ,,…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a New Series of Furopyranone‐ and Furocoumarin‐Chromone Conjugates Followed by In–Vitro Cytotoxicity Activity Evaluation, and Molecular Docking Study

et al. 2019

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In this work, new furopyranone‐ and furocoumarin‐chromone conjugates were successfully synthesized via the one‐pot three‐component condensation reactions of 3‐formylchromone derivatives, 4‐hydroxy‐6‐methylpyrone or 4‐hydroxycoumarin and alkyl or aryl isocyanides in refluxing toluene within 2 h. Molecular docking studies on cyclooxygenase enzymes (COX‐1, COX‐2) indicated that most derivatives have greater or moderate binding affinities than 3‐formylchromone which was used as a reference compound. Even some of the new products showed comparable binding energy towards the relative co‐crystalized ligand into COX‐1 and COX‐2. In general, all of the new products formed one to three hydrogen bonds with amino acid residues in the active site of both enzymes. Furthermore, the cytotoxicity activity of some selected compounds was investigated against human foreskin fibroblast cells (BJ) and human breast cancer cells (MDA‐MB‐231) using the MTT assay. All selected compounds exhibited significant cell growth inhibitory against cancerous cells with varied potencies when compared to 3‐formylchromone. However, they were much less toxic against normal cells.

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Section: Resultsmentioning

confidence: 99%

Synthesis of a New Series of Furopyranone‐ and Furocoumarin‐Chromone Conjugates Followed by In–Vitro Cytotoxicity Activity Evaluation, and Molecular Docking Study

et al. 2019

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“…To parameterize molecular docking study, the co‐crystallized ligands, ibuprofen, and SC‐58 were utilized as positive control ligands towards COX‐1 and COX‐2 enzymes, respectively. As cited in the literature, if the RMSD (root mean square deviation) of the best‐docked conformation of co‐crystal ligand is ≤ 2 Å from the experimental one the used scoring function is reliable. The RMSD value of 0.98 Å for ibuprofen and 1.57 Å for docked SC‐58 validated the accuracy of AutoDock 4.2 performance.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective One‐Pot Synthesis of Coumarin‐4‐carboxamido‐3‐esters via a Four‐Component Isocyanide‐Based Reaction and Molecular Docking Study

2018

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A facile and practical method has been developed for the stereoselective synthesis of coumarin‐4‐carboxamido‐3‐esters via a four‐component reaction between salicylaldehyde, malonic acid, alkyl or aryl isocyanides and various alcohols in acetonitrile at room temperature. Coumarin derivatives have been introduced to be effective in inhibition of cyclooxygenase pathways thus; the potential of new products for interaction into cyclooxygenase enzymes (COX‐1/COX‐2) was screened via in silico molecular docking towards the original compound as an assist for designing the potent inhibitors in the future studies.

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“…In order to improve the anti-inflammatory effect and safety profile of representative NSAIDs, one research strategy is derivatization of the carboxylic acid group with various heterocyclic systems (oxazole, izoxazole, pyrazole, oxadiazole, thiazole, thiadiazole, triazole, etc.) [9,10]. In the past two decades there has been considerable interest in the role of reactive oxygen species (ROS) in inflammation [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

et al. 2014

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New thiazolidine-4-one derivatives of 2-(4-isobutylphenyl)propionic acid (ibuprofen) have been synthesized as potential anti-inflammatory drugs. The structure of the new compounds was proved using spectral methods (FR-IR, 1 H-NMR, 13 C-NMR, MS). The in vitro antioxidant potential of the synthesized compounds was evaluated according to the total antioxidant activity, the DPPH and ABTS radical scavenging assays. Reactive oxygen species (ROS) and free radicals are considered to be involved in many pathological events like diabetes mellitus, neurodegenerative diseases, cancer, infections and more recently, in inflammation. It is known that overproduction of free radicals may initiate and amplify the inflammatory process via upregulation of genes involved in the production of proinflammatory cytokines and adhesion molecules. The chemical modulation of acyl hydrazones of ibuprofen 3a-l through cyclization to the corresponding thiazolidine-4-ones 4a-n led to increased antioxidant potential, as all thiazolidine-4-ones were more active than their parent acyl hydrazones and also ibuprofen. The most active compounds are the thiazolidine-4-ones 4e, m, which showed the highest DPPH radical scavenging ability, their activity being comparable with vitamin E.

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Synthesis, pharmacological screening and in silico studies of new class of Diclofenac analogues as a promising anti-inflammatory agents

Cited by 53 publications

References 42 publications

Synthesis of a New Series of Furopyranone‐ and Furocoumarin‐Chromone Conjugates Followed by In–Vitro Cytotoxicity Activity Evaluation, and Molecular Docking Study

Synthesis of a New Series of Furopyranone‐ and Furocoumarin‐Chromone Conjugates Followed by In–Vitro Cytotoxicity Activity Evaluation, and Molecular Docking Study

Diastereoselective One‐Pot Synthesis of Coumarin‐4‐carboxamido‐3‐esters via a Four‐Component Isocyanide‐Based Reaction and Molecular Docking Study

Synthesis and Biological Evaluation of New 1,3-Thiazolidine-4-one Derivatives of 2-(4-Isobutylphenyl)propionic Acid

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