Novel 1-(4-arylthiazol-2-yl)-2-(3-methylcyclohexylidene)hydrazine derivatives have been investigated for their ability to inhibit selectively the activity of the human B isoform of monoamine oxidase. These compounds were obtained as racemates and (R)-enantiomers by a stereoconservative synthetic pattern in high yield and enantiomeric excess. The (S)-enantiomers of the most active derivatives have been separated by enantioselective HPLC. All compounds showed selective activity against hMAO-B with IC(50) ranging between 21.90 and 0.018 microM.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jm100120s | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Catalytic Enantioselective Synthesis of 1,4-(Hetero) Dicarbonyl Compounds through α-Carbonyl Umpolung.
J Am Chem Soc
January 2025
Institute of Organic Chemistry, University of Leipzig, 04103 Leipzig, Germany.
The enantioselective synthesis of 1,4-dicarbonyl compounds continues to pose a significant challenge in organic synthesis, and a catalytic process which generates two adjacent stereogenic centers with full stereochemical control is lacking until now. The 1,4-relationship of the functional groups requires an Umpolung strategy as one of the α-carbonyl positions has to be inverted into an electrophilic center to react with a normal enolate. We report herein the highly enantio- and diastereoselective addition of silyl ketene acetals toward electrophilic 1-azaallyl cations to furnish chiral 4-hydrazonoesters, which are masked 1,4-dicarbonyl compounds.
View Article and Find Full Text PDFWhat Factors Determine the Brevione B Desaturation Mechanism in the Nonheme Iron Dioxygenase BrvJ?
Chemistry
January 2025
The University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN, Manchester, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
The natural product synthesis of brevione J undergoes a cascade of reactions including an oxidative desaturation and a ring-expansion. The C1-C2 desaturation of brevione B is catalyzed by the nonheme iron dioxygenase BrvJ using one molecule of O2 and a-ketoglutarate (aKG). However, whether the subsequent oxidative ring expansion reaction is also catalyzed by the same enzyme is unknown and remains controversial.
View Article and Find Full Text PDFAccess to fluorinated dienes through hydrofluorination of 2-En-4-ynoates.
Org Chem Front
December 2024
Department of Chemistry, University of Pittsburgh Pittsburgh Pennsylvania 15260 USA
Article Synopsis
- The hydrofluorination of enynoates allows for the efficient synthesis of fluorinated dienoates using a pyridinium tetrafluoroborate salt.
- This method effectively converts various aryl-substituted enynoates into the desired fluorinated products with significant control over their stereochemistry and regioselectivity.
- Mechanistic studies were performed to understand the reaction process better and to optimize the outcomes based on different reaction conditions.
The synthesis of higher-carbon sugar alcohols via indium-mediated acyloxyallylation as potential phase change materials.
Monatsh Chem
December 2023
Institute of Applied Synthetic Chemistry, TU Wien, Vienna, Austria.
Unlabelled: In recent years, sugar alcohols have gained significant attention as organic phase change materials (PCMs) for thermal energy storage due to their comparably high thermal storage densities up to 350 J/g. In a computational study, outstandingly high values of up to ~ 450-500 J/g have been postulated for specific higher-carbon sugar alcohols. These optimized structures feature an even number of carbon atoms in the backbone and a stereochemical configuration in which all hydroxyl groups are in an 1,3--relationship, as found in the natural hexitol d-mannitol.
View Article and Find Full Text PDFTotal Synthesis of Kasugamycin.
Org Lett
January 2025
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, Wuhan, Hubei 430030, P.R. China.
We present an efficient synthetic pathway for kasugamycin, an aminoglycoside antibiotic, utilizing naturally derived carbohydrates as starting materials. This synthesis effectively addresses stereochemical complexities by employing the selective reduction of d-fucal, which generates a crucial 3-deoxyglycal intermediate. This intermediate facilitates the introduction of amino groups at the C-2 and C-4 positions, which is essential for the synthesis of kasugamine.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!