Synthesis and structure–activity relationship of cyclopentenone oximes as novel inhibitors of the production of tumor necrosis factor-α

Kim, Yeonjoon; Hong, Yong Deog; Joo, Yung Hyup; Woo, Byung Young; Kim, Sun‐Young; Koh, Hyun Ju; Park, Mi-Young; Byoun, Kyoung Hee; Shin, Song Seok

doi:10.1016/j.bmcl.2014.04.115

Cited by 6 publications

(4 citation statements)

References 9 publications

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“…Ligands preparation. Twenty six reported biologically active inhibitors (IC 50 in the range of 0.001-100 µm) against TNF-α were retrieved from the literature ( Supplementary Table S1) [15][16][17][18][19][20][21][22][23][24][25] . All the ligands were sketched in MOE 26 using builder module.…”

Section: Methodsmentioning

confidence: 99%

Identification of potential TNF-α inhibitors: from in silico to in vitro studies

Zia

Ashraf

Jabeen

et al. 2020

Sci Rep

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Tumor Necrosis Factor Alpha (TNF-α) is a pleiotropic pro-inflammatory cytokine. It act as central biological regulator in critical immune functions, but its dysregulation has been linked with a number of diseases. Inhibition of TNF-α has considerable therapeutic potential for diseases such as cancer, diabetes, and especially autoimmune diseases. Despite the fact that many small molecule inhibitors have been identified against TNF-α, no orally active drug has been reported yet which demand an urgent need of a small molecule drug against TNF-α. This study focuses on the development of ligand-based selective pharmacophore model to perform virtual screening of plant origin natural product database for the identification of potential inhibitors against TNF-α. The resultant hits, identified as actives were evaluated by molecular docking studies to get insight into their potential binding interaction with the target protein. Based on pharmacophore matching, interacting residues, docking score, more affinity towards TNF-α with diverse scaffolds five compounds were selected for in vitro activity study. Experimental validation led to the identification of three chemically diverse potential compounds with the IC50 32.5 ± 4.5 µM, 6.5 ± 0.8 µM and 27.4 ± 1.7 µM, respectively.

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Section: Methodsmentioning

confidence: 99%

Identification of potential TNF-α inhibitors: from in silico to in vitro studies

Zia

Ashraf

Jabeen

et al. 2020

Sci Rep

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“…Shin et al reported the inhibition effect of cyclopentenone oximes against tumor necrosis factor-α . 18 Several oxime ethers were found to be antiproliferative active. 19 Besides their biological activities, oximes and O -substituted oxime ethers are also important compounds in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, ($E)$/($Z)$-isomerization, and DNA binding, antibacterial, and antifungal activities of novel oximes and $O$-substituted oxime ethers

Küçük¹,

Yusufoğlu²,

Açık³

et al. 2016

Turk J Chem

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A series of novel positional oximes (2a-2d), O -methyl oxime ethers (3a-3d), and O -benzyl oxime ethers (4a-4d) were synthesized in high yields starting from their corresponding methyl 3-, 4-, 6-, and 13-keto tetradecanoates.The synthesized compounds were characterized by 1 H NMR, 13 C NMR, FT-IR, mass, and elemental analyses for their structures and ( E) /( Z) isomerizations. Their DNA binding abilities were investigated in vitro by agarose gel electrophoresis. The antibacterial and antifungal activities were tested also in vitro against eleven bacterial strains and three fungal strains. The relationship between the structure and the mentioned biological activities was discussed.Compound 2a showed good antibacterial activity against five types of bacteria. Compounds 2b, 2c, 2d, and 4d were effective against several microorganisms. Among these, 2a showed the best DNA binding, antibacterial, and antifungal activities. Therefore, 2a can be a pro-drug as an anticancer, antibacterial, and antifungal agent.

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“…Both compounds 25 a and 25 b are more potent than rolipram (IC 50 value 0.2 μM) and also highly active against TNF-α than rolipram (IC 50 value 0.27 μM) with IC 50 values ranging from 0.024-4.59 μM. [48]…”

Section: Cyclopentanone-based Oxime Derivativesmentioning

confidence: 94%

Oxime Derivatives: A Valid Pharmacophore in Medicinal Chemistry

Chandran,

Bose,

Thekkantavida

et al. 2024

ChemistrySelect

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Oximes, belonging to imines with the general formula of RR'C=NOH, are produced by the nucleophilic addition reaction between hydroxylamine with ketones or aldehydes, yielding corresponding aldoxime and ketoxime. The presence of hydrogen bond acceptor and donor is the classical feature of oxime‐containing structural framework. This review presents a summary of the role of oximes and its structure activity relationships including antimicrobial, anticancer, anti‐inflammatory, antihyperglycemic, insecticidal agents, along with their involvement in the treatment of organophosphorus poisoning. The review also focused on the pharmacological profile of lead molecules of several classes of oxime‐containing compounds.

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Synthesis and structure–activity relationship of cyclopentenone oximes as novel inhibitors of the production of tumor necrosis factor-α

Cited by 6 publications

References 9 publications

Identification of potential TNF-α inhibitors: from in silico to in vitro studies

Identification of potential TNF-α inhibitors: from in silico to in vitro studies

Synthesis, ($E)$/($Z)$-isomerization, and DNA binding, antibacterial, and antifungal activities of novel oximes and $O$-substituted oxime ethers

Oxime Derivatives: A Valid Pharmacophore in Medicinal Chemistry

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