Issue 6, 2010

Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives

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⋯S interactions and three of the structures have N–H⋯O linked H-bonded chains.

Graphical abstract: Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives

Supplementary files

Article information

Article type
Paper
Submitted
25 Nov 2009
Accepted
09 Feb 2010
First published
05 Mar 2010

CrystEngComm, 2010,12, 1730-1739

Hydrogen bonded dimers vs. one-dimensional chains in 2-thiooxoimidazolidin-4-one (thiohydantoin) drug derivatives

S. Jha, J. D. Silversides, R. W. Boyle and S. J. Archibald, CrystEngComm, 2010, 12, 1730 DOI: 10.1039/B924683E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements