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Molecules 2017, 22(4), 626; doi:10.3390/molecules22040626

One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors

1
Department of Chemistry, University College London, Christopher Ingold Laboratories, 20 Gordon Street, London WC1H 0AJ, UK
2
The Advanced Centre for Biochemical Engineering, Department of Biochemical Engineering, University College London, Bernard Katz Building, Gower Street, London WC1E 6BT, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Margaret A. Brimble
Received: 17 March 2017 / Revised: 7 April 2017 / Accepted: 9 April 2017 / Published: 12 April 2017
(This article belongs to the Special Issue Women in Organic Chemistry)
View Full-Text   |   Download PDF [3315 KB, uploaded 14 April 2017]   |  

Abstract

Polysubstituted pyridinium salts are valuable pharmacophores found in many biologically active molecules. Their synthesis typically involves the use of multistep procedures or harsh reaction conditions. Here, we report water-based phosphate mediated reaction conditions that promote the condensation of arylacetaldehydes with amines to give 1,3,5-pyridinium salts. The reaction, carried out at pH 6, provides conditions suitable for the use of less stable aldehydes and amines in this Chichibabin pyridine condensation. The evaluation of selected 1,3,5-trisubstituted pyridinium salts highlighted that they can inhibit the growth of S. aureus in the low μg/mL range. The synthetic accessibility of these compounds and preliminary growth inhibition data may pave the way towards the discovery of new anti-bacterials based on the 1,3,5-trisubstituted pyridinium scaffold. View Full-Text
Keywords: heteroaromatic synthesis; Chichibabin reaction; synthesis in water; pyridinium salts; antibacterial activity heteroaromatic synthesis; Chichibabin reaction; synthesis in water; pyridinium salts; antibacterial activity
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Pesnot, T.; Gershater, M.C.; Edwards, M.; Ward, J.M.; Hailes, H.C. One–Pot Phosphate-Mediated Synthesis of Novel 1,3,5-Trisubstituted Pyridinium Salts: A New Family of S. aureus Inhibitors. Molecules 2017, 22, 626.

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