2,3-Dihydrobenzofuran privileged structures as new bioinspired lead compounds for the design of mPGES-1 inhibitors

Micco, Simone Di; Spatafora, Carmela; Cardullo, Nunzio; Riccio, Raffaele; Fischer, Katrin; Pergola, Carlo; Koeberle, Andreas; Werz, Oliver; Chalal, Malik; Vervandier‐Fasseur, Dominique; Tringali, Corrado; Bifulco, Giuseppe

doi:10.1016/j.bmc.2016.01.002

Cited by 46 publications

(28 citation statements)

References 46 publications

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“…Moreover, AAD‐2004 exhibited neuroprotective actions in rodent models of amyotrophic lateral sclerosis and Alzheimer's disease . Furthermore, the combination of computational studies with in vitro experiments allowed the description of natural products derivatives, namely, curcumin prenylated analogs and bioinspired 2,3‐dihydrobenzofuran derivatives, as potent mPGES‐1 inhibitors in the micromolar range . Additionally, petrosaspongiolide M, a marine sesterterpene with anti‐inflammatory properties, was used as leader to generate three libraries of γ‐hydroxybutenolide derivatives, from which inhibitors of mPGES‐1 expression and of mPGES‐1 activity were identified .…”

Section: Identification Of Novel Targets In the Arachidonic Acid Cascadementioning

confidence: 99%

Nonsteroidal Anti‐Inflammatory Therapy: A Journey Toward Safety

Pereira-Leite

Nunes

Jamal

et al. 2016

Medicinal Research Reviews

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The efficacy of nonsteroidal anti-inflammatory drugs (NSAIDs) against inflammation, pain, and fever has been supporting their worldwide use in the treatment of painful conditions and chronic inflammatory diseases until today. However, the long-term therapy with NSAIDs was soon associated with high incidences of adverse events in the gastrointestinal tract. Therefore, the search for novel drugs with improved safety has begun with COX-2 selective inhibitors (coxibs) being straightaway developed and commercialized. Nevertheless, the excitement has fast turned to disappointment when diverse coxibs were withdrawn from the market due to cardiovascular toxicity. Such events have once again triggered the emergence of different strategies to overcome NSAIDs toxicity. Here, an integrative review is provided to address the breakthroughs of two main approaches: (i) the association of NSAIDs with protective mediators and (ii) the design of novel compounds to target downstream and/or multiple enzymes of the arachidonic acid cascade. To date, just one phosphatidylcholine-associated NSAID has already been approved for commercialization. Nevertheless, the preclinical and clinical data obtained so far indicate that both strategies may improve the safety of nonsteroidal anti-inflammatory therapy.

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Section: Identification Of Novel Targets In the Arachidonic Acid Cascadementioning

confidence: 99%

Nonsteroidal Anti‐Inflammatory Therapy: A Journey Toward Safety

Pereira-Leite

Nunes

Jamal

et al. 2016

Medicinal Research Reviews

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“…In addition to the investigation for inhibitory activity on NO production in the present study, similar dihydrobenzofuran derivatives have been described as new generation mPGES-1 inhibitors, 28 showing inhibitory activity against ADP-or collagen-induced platelet aggredation, 29 and an in vivo study for antinociceptive activity in models of chemical pain occurred through ATPsensitive K + chanel-dependent mechanisms. 30 This study provided some of the information on the 13 constituents of S. tamariscina and subsequently evaluated their inhibitory activity on LPSstimulated activity in RAW 264.7 cells.…”

Section: Nitric Oxide (No) Is An Important Inter-and Intracellular Simentioning

confidence: 96%

Lignan derivatives from Selaginella tamariscina and their nitric oxide inhibitory effects in LPS-stimulated RAW 264.7 cells

Zhao

Hùng

et al. 2017

Bioorganic & Medicinal Chemistry Letters

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“…Dihydrobenzofurans and indolines are two common structural motifs in natural products, bioactive molecules and pharmaceuticals. For example, compounds I , II and III (Figure ) possess cytotoxic and anti‐inflammatory activities and are promising drug candidates . From the retrosynthesis perspective, compounds I , II and III can all be synthesized from one type of versatile intermediate IV .…”

Section: Figurementioning

confidence: 99%

“…For example, compounds I, II and III (Figure 1) possess cytotoxic and anti-inflammatory activities and are promisingd rug candidates. [3][4][5] From the retrosynthesis perspective, compounds I, II and III can all be synthesizedf rom one type of versatile intermediate IV.T hus,m ethods that can readily create the general structure IV would be highly desirable.…”

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confidence: 99%

Photo‐induced Carboiodination: A Simple Way to Synthesize Functionalized Dihydrobenzofurans and Indolines

Yang

Liu

et al. 2016

Chemistry A European J

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Herein, we report a simple, redox-neutral and pH-neutral photo-induced carboiodination reaction under very mild conditions. This protocol employs readily available and cheap aryl bromides and sodium iodide as the starting materials to synthesize valuable functionalized dihydrobenzofurans and indolines in good to excellent yields with broad functional-group compatibility. As examples to demonstrate the utility of this protocol, gram-scale reactions and further transformations of the products were accomplished towards the synthesis of bioactive drug candidates. Most significantly, to the best of our knowledge, this reaction represents the first example of a cascade atom-radical-transfer addition involving the cleavage of aromatic C-Br bond.

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2,3-Dihydrobenzofuran privileged structures as new bioinspired lead compounds for the design of mPGES-1 inhibitors

Cited by 46 publications

References 46 publications

Nonsteroidal Anti‐Inflammatory Therapy: A Journey Toward Safety

Nonsteroidal Anti‐Inflammatory Therapy: A Journey Toward Safety

Lignan derivatives from Selaginella tamariscina and their nitric oxide inhibitory effects in LPS-stimulated RAW 264.7 cells

Photo‐induced Carboiodination: A Simple Way to Synthesize Functionalized Dihydrobenzofurans and Indolines

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