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; Edward R.T. Tiekink

doi:10.1515/zkri-2014-1830

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

From the journal Zeitschrift für Kristallographie - Crystalline Materials

https://doi.org/10.1515/zkri-2014-1830

Showing a limited preview of this publication:

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.

Keywords: crystal structure analysis; hydrogen bonding; salt; sulfathiazole; X-ray diffraction

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: ykcheah@medic.upm.edu.my; and Edward R.T. Tiekink, Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, E-mail: edward.tiekink@gmail.com

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

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

Abstract

Acknowledgments

References

Supplemental Material

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