ArticleBioorganic chemistry2018
Effects of adamantane alterations on soluble epoxide hydrolase inhibition potency, physical properties and metabolic stability.
Article in Bioorganic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 67 citations in OpenAlex.
- Human breath as a carbon dioxide source for organic synthesis.RSC advances · 2026Article
- Indole Alkaloids and Phenolic Amides from the Rhizomes ofPlants (Basel, Switzerland) · 2025Article
- 1,3-Dichloroadamantyl-Containing Ureas as Potential Triple Inhibitors of Soluble Epoxide Hydrolase, p38 MAPK and c-Raf.International journal of molecular sciences · 2023Article
- Fluorine and chlorine substituted adamantyl-urea as molecular tools for inhibition of human soluble epoxide hydrolase with picomolar efficacy.Journal of enzyme inhibition and medicinal chemistry · 2023Article
- Synthesis and Properties of 1,3-Disubstituted Ureas Containing (Adamantan-1-yl)(phenyl)methyl Fragment Based on One-Pot Direct Adamantane Moiety Inclusion.Molecules (Basel, Switzerland) · 2023Article
- Adamantyl-ureas with pyrazoles substituted by fluoroalkanes as soluble epoxide hydrolase inhibitors.Journal of fluorine chemistry · 2023Article
- Anti-Inflammatory Activity of Soluble Epoxide Hydrolase Inhibitors Based on Selenoureas Bearing an Adamantane Moiety.International journal of molecular sciences · 2022Article
- Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.Journal of medicinal chemistry · 2022Article
- Ureas derived from camphor and fenchone reveal enantiomeric preference of human soluble epoxide hydrolase.Results in chemistry · 2022Article
- From the Design to theJournal of medicinal chemistry · 2021Article
- Discovery of Soluble Epoxide Hydrolase Inhibitors from Chemical Synthesis and Natural Products.Journal of medicinal chemistry · 2021Review
- Adamantane-linked isothiourea derivatives suppress the growth of experimental hepatocellular carcinomaAmerican journal of cancer research · 2021Article
- Preparation and evaluation of soluble epoxide hydrolase inhibitors with improved physical properties and potencies for treating diabetic neuropathic pain.Bioorganic & medicinal chemistry · 2020Article
- Bioisosteric substitution of adamantane with bicyclic lipophilic groups improves water solubility of human soluble epoxide hydrolase inhibitors.Bioorganic & medicinal chemistry letters · 2020Article
- Polycarbonate/Sulfonamide Composites with Ultralow Contents of Halogen-Free Flame Retardant and Desirable Compatibility.Materials (Basel, Switzerland) · 2020Article
- Protostane-type triterpenoids as natural soluble epoxide hydrolase inhibitors: Inhibition potentials and molecular dynamics.Bioorganic chemistry · 2020Article
- Imidazolidine-2,4,5- and pirimidine-2,4,6-triones - New primary pharmacophore for soluble epoxide hydrolase inhibitors with enhanced water solubility.Bioorganic & medicinal chemistry letters · 2020Article
- Metabolic Profiling of a CB2 Agonist, AM9338, Using LC-MS and Microcoil-NMR: Identification of a Novel Dihydroxy Adamantyl Metabolite.Frontiers in pharmacology · 2020Article
- Exploring the size of the lipophilic unit of the soluble epoxide hydrolase inhibitors.Bioorganic & medicinal chemistry · 2019Article
- Fluoroaromatic fragments on 1,3-disubstituted ureas enhance soluble epoxide hydrolase inhibition.Journal of fluorine chemistry · 2019Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
Adamantyl groups are widely used in medicinal chemistry. However, metabolism limits their usage. Herein, we report the first systematic study of adamantyl ureas and diureas bearing substituents in bridgehead positions of adamantane and/or spacers between urea groups and adamantane group, and tested their effects on soluble epoxide hydrolase inhibitor potency and metabolic stability. Interestingly, the effect on activity against human and murine sEH varied in opposite ways with each new methyl group introduced into the molecule. Compounds with three methyl substituents in adamantane were very poor inhibitors of murine sEH while still very potent against human sEH. In addition, diureas with terminal groups bigger than sEH catalytic tunnel diameter were still good inhibitors suggesting that the active site of sEH opens to capture the substrate or inhibitor molecule. The introduction of one methyl group leads to 4-fold increase in potency without noticeable loss of metabolic stability compared to the unsubstituted adamantane. However, introduction of two or three methyl groups leads to 8-fold and 98-fold decrease in stability in human liver microsomes for the corresponding compounds.
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