Synthesis and Characterisation of Bismuth(III) Aminoarenesulfonate Complexes and Their Powerful Bactericidal Activity against Helicobacter pylori. Issue 17 (27th March 2013)

• Record Type: Journal Article
• Authors: Busse, Madleen; Trinh, Iman; Junk, Peter C.; Ferrero, Richard L.; Andrews, Philip C.
• Is Part Of: Chemistry. Volume 19:Issue 17(2013)
• Page Start: 5264
• Page End: 5275
• Publication Date: 2013-03-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201204220
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The synthesis and characterisation of nine new tris‐substituted bismuth(III) aminoarenesulfonates of the general formula [Bi(O<sub>3</sub>S‐R<sup>N</sup>)<sub>3</sub>] (R<sup>N</sup>=<italic>o</italic>‐aminophenyl <bold>1</bold>, <italic>m</italic>‐aminophenyl <bold>2</bold>, 6‐amino‐3‐methoxyphenyl <bold>3</bold>, <italic>p</italic>‐aminophenyl <bold>4</bold>, 2‐pyridyl <bold>5</bold>, <italic>o</italic>‐aminonaphthyl <bold>6</bold>, 5‐aminonaphthyl <bold>7</bold>, 4‐amino‐3‐hydroxynaphthyl <bold>8</bold> and 5‐isoquinolinyl <bold>9</bold>) is described. Two synthetic strategies, using Ag<sub>2</sub>O and [Bi(O<italic>t</italic>Bu)<sub>3</sub>], were explored and compared. The possibility to access heteroleptic bismuth(III) complexes with the new silver(I) metathesis reaction is demonstrated with the synthesis of the heteroleptic bismuth(III) aminoarenesulfonate complexes [PhBi(O<sub>3</sub>S‐P2)<sub>2</sub>(dmso)] <bold>10</bold>, [Ph<sub>2</sub>Bi(O<sub>3</sub>S‐P2)]<sub>∞</sub><bold>11</bold> and [PhBi(O<sub>3</sub>S‐P2)<sub>2</sub>]<sub>∞</sub><bold>12</bold>, of which the solid state structures <bold>10</bold> and <bold>12</bold> are presented (2P‐SO<sub>3</sub><sup>−</sup>=2‐pyridinesulfonate). These complexes offer remarkable in‐vitro activity against three standard laboratory strains of <italic>Helicobacter pylori</italic> (<italic>H. pylori</italic>) as demonstrated by their exceptionally low minimum inhibitory concentration (MIC) values of 0.049 μg mL<sup>−1</sup> for the strains 251 and B128, which places most MIC values in the nano‐molar region. These results demonstrate the importance of the amino functionality in addition to the sulfonate group on the bactericidal properties against <italic>H. pylori</italic>.</p> </abstract>