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Licensed Unlicensed Requires Authentication Published by De Gruyter (O) February 26, 2015

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

Aina Mardia Akhmad Aznan, Zanariah Abdullah, Chai-Hoon Khoo, Bao-Jing Chen, Tian-Hong See, Jiun-Horng Sim, Yoke-Kqueen Cheah, Hoi-Ling Seng and Edward R.T. Tiekink

Abstract

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.


Corresponding authors: Yoke-Kqueen Cheah, Faculty of Medicine and Health Sciences, Department of Biomedical Science, University Putra Malaysia, 43400 Serdang, Selangor Darul Ehsan, Malaysia, E-mail: ; and Edward R.T. Tiekink, Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, E-mail:

Acknowledgments

The University of Malaya X-ray Laboratory is thanked for providing the intensity data. The support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR-MOHE/SC/12) is gratefully acknowledged.

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Supplemental Material

The online version of this article (DOI: 10.1515/zkri-2014-1830) offers supplementary material, available to authorized users.


Received: 2014-12-21
Accepted: 2015-1-14
Published Online: 2015-2-26
Published in Print: 2015-6-1

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