ChemInform Abstract: Synthesis and Antibacterial Properties of β-Diketone Acrylate Bioisosteres of Pseudomonic Acid A.

✍ Scribed by Isobel Bennett; Nigel J. P. Broom; Robert Cassels; John S. Elder; Nicky D. Masson; Peter J. O'Hanlon

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199943264

✦ Synopsis

Synthesis and Antibacterial Properties of β-Diketone Acrylate Bioisosteres of Pseudomonic Acid A. -Fourteen bioisosteres like (V) and (IX) are synthesized and evaluated for their antibacterial activities. The first synthesis of the diketone system (V) uses a base-catalyzed deconjugation process. The second synthesis of system (IX) is complementary to that of system (V) and the ready availability of aldehydes (VII) makes this synthesis the preferred sequence. Optimal activity is observed with small para-phenyl substituents as in (Va) and (IXa). Furthermore, the ring is not necessarily aromatic, cf. (IXb). However, the antibacterial activity of (Vb) with an alkyl chain is poor.