ArticleThe Journal of organic chemistry2014
Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 49 citations in OpenAlex.
- Chiral Monoamidines as Effective Organocatalysts for the Stereoselective Synthesis of Oxindoles under Homogeneous and Heterogeneous Conditions.The Journal of organic chemistry · 2025Article
- Elucidating Fluorine Steering Effects in Diels-Alder Reactions Interfaced with Charge-Enhanced Reactivity.European journal of organic chemistry · 2025Article
- Nutlin-3 Loaded Ethosomes and Transethosomes to Prevent UV-Associated Skin Damage.Life (Basel, Switzerland) · 2024Article
- Microfluidic Fabricated Liposomes for Nutlin-3a Ocular Delivery as Potential Candidate for Proliferative Vitreoretinal Diseases Treatment.International journal of nanomedicine · 2024Article
- Secondary Orbital Effect Involving Fluorine is Responsible for Substrate-Controlled Diastereodivergence in the Catalyzed syn-aza-Henry Reaction of α-Fluoronitroalkanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Fluorine-induced diastereodivergence discovered in an equally rare enantioselectiveChemical science · 2022Article
- Leveraging the multivalent p53 peptide-MdmX interaction to guide the improvement of small molecule inhibitors.Nature communications · 2022Article
- Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide).Molecules (Basel, Switzerland) · 2021Article
- Substituted Imidazoline Synthesis: A Diastereo- and Enantioselective aza-Henry Route to a Human Proteasome Modulator.Organic letters · 2020Article
- Recent Synthetic Approaches towards Small Molecule Reactivators of p53.Biomolecules · 2020Review
- The inverted ketene synthon: a double umpolung approach to enantioselective βChemical science · 2019Article
- Continuous Platform to Generate Nitroalkanes On-Demand (in situ) using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor.Organic process research & development · 2018Article
- One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions.PeerJ · 2018Article
- Performance of a docking/molecular dynamics protocol for virtual screening of nutlin-class inhibitors of Mdmx.Journal of molecular graphics & modelling · 2017Article
- Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.Journal of the American Chemical Society · 2016Article
- Monitoring Ligand-Induced Protein Ordering in Drug Discovery.Journal of molecular biology · 2016Article
- Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.Organic process research & development · 2016Article
- Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis ofTetrahedron letters · 2015Article
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
The finding by scientists at Hoffmann-La Roche that cis-imidazolines could disrupt the protein-protein interaction between p53 and MDM2, thereby inducing apoptosis in cancer cells, raised considerable interest in this scaffold over the past decade. Initial routes to these small molecules (i.e., Nutlin-3) provided only the racemic form, with enantiomers being enriched by chromatographic separation using high-pressure liquid chromatography (HPLC) and a chiral stationary phase. Reported here is the first application of an enantioselective aza-Henry approach to nonsymmetric cis-stilbene diamines and cis-imidazolines. Two novel mono(amidine) organocatalysts (MAM) were discovered to provide high levels of enantioselection (>95% ee) across a broad range of substrate combinations. Furthermore, the versatility of the aza-Henry strategy for preparing nonsymmetric cis-imidazolines is illustrated by a comparison of the roles of aryl nitromethane and aryl aldimine in the key step, which revealed unique substrate electronic effects providing direction for aza-Henry substrate-catalyst matching. This method was used to prepare highly substituted cis-4,5-diaryl imidazolines that project unique aromatic rings, and these were evaluated for MDM2-p53 inhibition in a fluorescence polarization assay. The diversification of access to cis-stilbene diamine-derived imidazolines provided by this platform should streamline their further development as chemical tools for disrupting protein-protein interactions.
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