Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives
Jha, Sushil; Silversides, Jon D.; Boyle, Ross W.; Archibald, Stephen J.
Jon D. Silversides
Professor Ross Boyle R.W.Boyle@hull.ac.uk
Professor of Biological Chemistry
Professor Steve Archibald S.J.Archibald@hull.ac.uk
Professor in Molecular Imaging Chemistry
Hydantoins have been known as medicinally active compounds since the 1940s and thiohydantoin derivatives are currently undergoing clinical trials as potent androgen receptor antagonist drugs. Control of solid state properties including the formation of drug polymorphs is important to the pharmaceutical industry, and frequently results from different H-bonded motifs. N-H thiohydantoins show formation of H-bonded arrays in the solid state. Two novel and five known thiohydantoin derivatives were synthesised via reaction of alkyl isothiocyanates with amino acid methyl esters. X-Ray crystallographic data were obtained for all seven compounds showing that four of the structures contain hydrogen bonded dimeric units linked via N-H center dot center dot center dot S interactions and three of the structures have N-H center dot center dot center dot O linked H-bonded chains.
|Journal Article Type||Article|
|Publication Date||Jun 1, 2010|
|Publisher||Royal Society of Chemistry|
|Peer Reviewed||Peer Reviewed|
|APA6 Citation||Jha, S., Silversides, J. D., Boyle, R. W., & Archibald, S. J. (2010). Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives. CrystEngComm RSC, 12(6), 1730-1739. https://doi.org/10.1039/b924683e|
|Keywords||General Materials Science; General Chemistry; Condensed Matter Physics|
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