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  • Title: Stereocontrolled facile synthesis and antimicrobial activity of oximes and oxime ethers of diversely substituted bispidines.
    Author: Parthiban P, Kabilan S, Ramkumar V, Jeong YT.
    Journal: Bioorg Med Chem Lett; 2010 Nov 15; 20(22):6452-8. PubMed ID: 20933407.
    Abstract:
    A small library of diversely substituted 2,4,6,8-tetraaryl-3,7-diazabicyco[3.3.1]nonan-9-ones, their oximes and O-methyloximes were achieved in a stereocontrolled manner by an easiest synthetic strategy as single isomers with high yields. Stereochemistry of all the synthesized compounds was established by their 1D/2D NMR spectral studies, further, witnessed by single-crystal XRD analysis. Accordingly, the compounds exist in a chair-boat conformation with equatorial orientation of the substituents in the chair part and boat-axial orientation in the boat part. Finally, all the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity against a panel of pathogenic bacteria and fungi, and as a result of the structure-activity correlations, some lead molecules were known for further optimization.
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