ArticleChemMedChem2009
2,3-Dihydro-1-benzofuran derivatives as a series of potent selective cannabinoid receptor 2 agonists: design, synthesis, and binding mode prediction through ligand-steered modeling.
Article in ChemMedChem, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 86 citations in OpenAlex.
- Latest developments in small molecule analgesics: heterocyclic scaffolds II.Future medicinal chemistry · 2025Review
- Enantioselective Synthesis of 3,3-Disubstituted-2,3-dihydrobenzofurans by Intramolecular Heck-Matsuda/Carbonylation/Stille Coupling.The Journal of organic chemistry · 2025Article
- Characterization of Novel and Known Activators of Cannabinoid Receptor Subtype 2 Reveals Mixed Pharmacology That Differentiates Mycophenolate Mofetil and GW-842,166X from MDA7.International journal of molecular sciences · 2025Article
- Neuroinflammation in the Central Nervous System: Exploring the Evolving Influence of Endocannabinoid System.Biomedicines · 2023Review
- Goods and Bads of the Endocannabinoid System as a Therapeutic Target: Lessons Learned after 30 Years.Pharmacological reviews · 2023Review
- Microglial Cannabinoid CBInternational journal of molecular sciences · 2023Review
- Ni-Catalyzed Oxygen Transfer from NJournal of the American Chemical Society · 2022Article
- RhodiumChemical science · 2022Article
- Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans.Journal of the American Chemical Society · 2022Article
- Enantioselective difunctionalization of alkenes by a palladium-catalyzed Heck/borylation sequence.Chemical science · 2022Article
- An overview of the cannabinoid type 2 receptor system and its therapeutic potential.Current opinion in anaesthesiology · 2018Review
- High throughput screening for inhibitors of the HECT ubiquitin E3 ligase ITCH identifies antidepressant drugs as regulators of autophagy.Cell death & disease · 2014Article
- Multi-Target-Directed Ligands and other Therapeutic Strategies in the Search of a Real Solution for Alzheimer's Disease.Current neuropharmacology · 2014Article
- Mastering tricyclic ring systems for desirable functional cannabinoid activity.European journal of medicinal chemistry · 2013Article
- In vivo efficacy of enabling formulations based on hydroxypropyl-β-cyclodextrins, micellar preparation, and liposomes for the lipophilic cannabinoid CB2 agonist, MDA7.Journal of pharmaceutical sciences · 2013Article
- Article
- Prevention of paclitaxel-induced neuropathy through activation of the central cannabinoid type 2 receptor system.Anesthesia and analgesia · 2012Article
- Homology modeling a fast tool for drug discovery: current perspectives.Indian journal of pharmaceutical sciences · 2012Article
- From laptop to benchtop to bedside: structure-based drug design on protein targets.Current pharmaceutical design · 2012Review
- Docking-based virtual screening for ligands of G protein-coupled receptors: not only crystal structures but also in silico models.Journal of molecular graphics & modelling · 2011Article
Corrections and comments
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Authors and funding
8 authors at 4 institutions in 1 country.
Funding
Abstract
We recently discovered and reported a series of N-alkyl-isatin acylhydrazone derivatives that are potent cannabinoid receptor 2 (CB(2)) agonists. In an effort to improve the druglike properties of these compounds and to better understand and improve the treatment of neuropathic pain, we designed and synthesized a new series of 2,3-dihydro-1-benzofuran derivatives bearing an asymmetric carbon atom that behave as potent selective CB(2) agonists. We used a multidisciplinary medicinal chemistry approach with binding mode prediction through ligand-steered modeling. Enantiomer separation and configuration assignment were carried out for the racemic mixture for the most selective compound, MDA7 (compound 18). It appeared that the S enantiomer, compound MDA104 (compound 33), was the active enantiomer. Compounds MDA42 (compound 19) and MDA39 (compound 30) were the most potent at CB(2). MDA42 was tested in a model of neuropathic pain and exhibited activity in the same range as that of MDA7. Preliminary ADMET studies for MDA7 were performed and did not reveal any problems.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.