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.

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.

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

• Journal Article Type: Article
• Acceptance Date: Feb 9, 2010
• Online Publication Date: Mar 5, 2010
• 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
• DOI: https://doi.org/10.1039/b924683e
• Keywords: General Materials Science; General Chemistry; Condensed Matter Physics
• Public URL: https://hull-repository.worktribe.com/output/391647