Making Bispirin: synthesis, structure and activity against Helicobacter pylori of bismuth(III) acetylsalicylate

Philip C. Andrews; Victoria L. Blair; Richard L. Ferrero; Peter C. Junk; Ish Kumar

doi:10.1039/C3CC40645H

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Chemical Communications

Issue 28, 2013

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Making Bispirin: synthesis, structure and activity against Helicobacter pylori of bismuth(III) acetylsalicylate

Philip C. Andrews,*^a Victoria L. Blair,^a Richard L. Ferrero,^b Peter C. Junk^c and Ish Kumar^a

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School of Chemistry, Monash University, Clayton, Melbourne, Australia
E-mail: phil.andrews@monash.edu

Monash Institute of Medical Research, Centre for Innate Immunity and Infectious Diseases Monash University, Clayton, Melbourne, Australia

School of Pharmacy and Molecular Sciences, James Cook University, Townsville, Australia

Chem. Commun., 2013,49, 2870-2872

DOI: 10.1039/C3CC40645H
Received 25 Jan 2013, Accepted 21 Feb 2013
First published online 22 Feb 2013

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Reaction of Bi(O^tBu)₃ with aspirin (acetylsalicylic acid = aspH) in dry toluene results in the bismuth(III) complex, [Bi(O₂C(C₆H₄)OAc)₃]_∞ 1 (O₂C(C₆H₄)OAc = asp), minimum inhibitory concentration (MIC) against Helicobacter pylori ≥ 6.25 μg mL⁻¹, while the inclusion of a stoichiometric equivalent of KO^tBu leads to crystals of the bismuthate salt [KBi(O₂C(C₆H₄)OAc)₄]_∞ 2.

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Philip C. Andrews
Victoria L. Blair
Richard L. Ferrero
Peter C. Junk
Ish Kumar

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