Three ammonium salts of sulfathiazole: crystallography and anti-microbial assay

• Main Authors: Akhmad Aznan, Aina Mardia, Abdullah, Zanariah, Khoo, Chai Hoon, Chen, Bao Jing, See, Tian Hong, Sim, Jiun Horng, Cheah, Yoke Kqueen, Seng, Hoi Ling, Tiekink, Edward R.T.
• Format: Article
• Language: English
• Published: Walter de Gruyter GmbH 2015
• Online Access: http://psasir.upm.edu.my/id/eprint/46730/1/Three%20ammonium%20salts%20of%20sulfathiazole%3B%20crystallography%20and%20anti-microbial%20assay.pdf; http://psasir.upm.edu.my/id/eprint/46730/; https://www.degruyter.com/document/doi/10.1515/zkri-2014-1830/html?lang=en

The crystal and molecular structures of three ammonium salts derived from sulfathiazole are described. In each case, the anion is in the azanide form, features an intramolecular S←O interaction, and adopts a U-shape. The structures of two cations, [R(HOCH2CH2)NH2]+, namely for R = Me (1) and iPr (2), are unprecedented in the crystallographic literature. Extensive hydrogen bonding is observed in all crystal structures and leads to a two-dimensional array for 1, and three-dimensional architectures for each of 2 and 3 (R = CH2CH2OH). The salts exhibited anti-microbial activity against a range of Gram-positive and Gram-negative bacteria, and proved bactericidal toward Vibrio parahaemolyticus, but had no advantage over sulfathiazole itself.