- Voltammetric Studies on Some Substituted 5-Arylidene-2-Thiohydantoin in non Aqueous Medium
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Differently substituted 5-arylidene-2-thiohydantions (2a-f) were studied electrochemically in benzonitrile with 0.1 M tetra-n-butylammonium-perchlorate as supportin electrolyte using DC-, cyclic voltammetry (CV), coulometry and controlled potential electr
- Abou-Elenien, G. M.,Ismail, N. A.,Eldin, A. A. Magd
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- Bicyclic imidazole-4-one derivatives: A new class of antagonists for the orphan G protein-coupled receptors GPR18 and GPR55
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GPR18 and GPR55 are orphan G protein-coupled receptors (GPCRs) that interact with certain cannabinoid (CB) receptor ligands. In the present study bicyclic imidazole-4-one derivatives were discovered as new scaffolds for the development of antagonists for
- Rempel,Atzler,Behrenswerth,Karcz,Schoeder,Hinz,Kaleta,Thimm,Kiec-Kononowicz,Müller
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p. 632 - 649
(2014/05/06)
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- Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry
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Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.
- Mendgen, Thomas,Steuer, Christian,Klein, Christian D.
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supporting information; experimental part
p. 743 - 753
(2012/03/11)
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- Synthesis and schistosomicidal activity of new substituted thioxo-imidazolidine compounds
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Synthesis and physico-chemical properties of 3-benzyl-5-(4-fluoro- benzylidene)-1-methyl-2-thioxo-imidazolidin-4-ones, 5-benzylidene-3-(4-nitro- benzyl)-2-thioxo-imidazolidin-4-onesand4-acridin-9-ylmethylene-1-benzyl-5- thioxo-imidazolidin-2-ones compounds are described. These thioxo-imidazolidine derivatives were prepared by alkylation and condensation with 4-fluoro-benzaldehyde or nucleophilic Michael addition with cyanoacrylates. The schistosomicidal activity of 3-benzyl-5-(4-fluoro-benzylidene)-1-methyl-2- thioxo-imidazolidin-4-one compounds was evaluated.
- Albuquerque,Silva,Pitta,Silva,Silva,Malagueno,Santana,Wanderley,Lima,Galdino,Barbe,Pitta, Ivan Rocha
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- Imidazo[2,1-b]thiazepines: Synthesis, structure and evaluation of benzodiazepine receptor binding
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As a continuation of our search for new ligands acting on benzodiazepine receptors among the fused 2-thiohydantoin derivatives, a series of 5-substituted imidazo[2,1-b]thiazepines was synthesized and investigated in radioligand binding studies at the benz
- Kiec-Kononowicz, Katarzyna,Karolak-Wojciechowska, Janina,Michalak, Barbara,Pekala, Elzbieta,Schumacher, Britta,Mueller, Christa E.
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p. 205 - 218
(2007/10/03)
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