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A new class of compounds featuring a camphor moiety has been discovered that exhibits potent inhibitory activity against influenza A(H1N1)pdm09 and A(H5N1) viruses. The synthesized compounds were characterized by spectroscopic analysis; in addition the structures of compound 2 and 14 were elucidated by the X-ray diffraction technique. Structure–activity relationship studies have been conducted to identify the 1,7,7-trimethylbicyclo[2.2.1]heptanes2-ylidene group as the key functional group responsible for the observed antiviral activity. The most potent antiviral compound is imine 2 with therapeutic index more than 500. [ABSTRACT FROM AUTHOR]

Smiles rearrangements occurring in the derivatives of the isoquinoline alkaloid, berberine, containing an oxyacetic acid fragment at C-9 are described. Methyl-2-(9-demethoxyberberinebromide-9-yl)oxyacetate reacts with an excess of propylamine followed by sequential aminolysis and Smiles rearrangement leading to 2-hydroxy- N -(berbero-9-yl)- N -propylacetamide in 80% yield. Reactions of berberrubine with secondary amides of bromoacetic acid via Smiles rearrangement give N-substituted 2-hydroxy- N -(berbero-9-yl)acetamides (yields 20–36%). In some cases, the intermediate secondary amides were isolated. [ABSTRACT FROM AUTHOR]

We report the synthesis and biological activity of new semi-synthetic derivatives of naturally occurring deoxycholic acid (DCA) bearing 2-cyano-3-oxo-1-ene, 3-oxo-1(2)-ene or 3-oxo-4(5)-ene moieties in ring A and 12-oxo or 12-oxo-9(11)-ene moieties in ring C. Bioassays using murine macrophage-like cells and tumour cells show that the presence of the 9(11)-double bond associated with the increased polarity of ring A or with isoxazole ring joined to ring A, improves the ability of the compounds to inhibit cancer cell growth. [ABSTRACT FROM AUTHOR]