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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.

Authors

Sushil Jha

Jon D. Silversides



Abstract

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
Journal CRYSTENGCOMM
Print ISSN 1466-8033
Electronic ISSN 1466-8033
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 12
Issue 6
Pages 1730-1739
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
DOI https://doi.org/10.1039/b924683e
Keywords General Materials Science; General Chemistry; Condensed Matter Physics
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