Homospisulosine induced apoptosis in cervical carcinoma cells is associated with phosphorylation of Bcl-2 and up-regulation of p27/Kip1.

Spisulosine (1-deoxysphinganine) is a sphingoid amino alcohol isolated from the sea clams that showed potent antiproliferative activity against a broad spectrum of solid tumors but failed in clinical trials due to neurotoxicity. However, its structural similarity to other bioactive sphingoids, interesting mode of action, and appreciable potency against cancer cells make it a suitable lead for future anticancer drug development. The present study was conducted to elucidate mechanisms of the antiproliferative/cytotoxic effects of newly synthesized spisulosine analog homospisulosine (KP7).

The convergent synthesis and anticancer activity of broussonetinines related analogues.

The convergent synthesis of broussonetinines related congeners 3 and 4 with the simple C alkyl side chain and differently configured pyrrolidine skeleton has been achieved. Our approach relied on the [3,3]-sigmatropic rearrangements of chiral allylic substrates derived from d-xylose. Cross metathesis of the common oxazolidinone intermediates 7 and 8 with tridec-1-ene followed by alkylative cyclization completed the construction of both C-alkyl iminosugars.

Total synthesis and antiproliferative/cytotoxic profiling of 2-epi-jaspine B.

A straightforward access to 2-epi-jaspine B (4.HCl) has been developed. Key to the approach was the use of Overman rearrangement for the instalment of a stereocentre bearing a nitrogen atom.