Phospholidines incorporating a beta N-sulfonylaminoalcohol moiety: first observed selectivity of phosphorus heterocycle aminolysis in the presence of water.

Eleven 2-oxo or 2-thioxo 3-sulfonyl 1,3,2-oxazaphospholidines were synthesized in one step by condensing P(IV) dichlorides with N-sulfonyl-ethanolamines, or -aminothexylalcohols or -ortho-aminophenols. These compounds, in contrast to all other phosphorus heterocycles studied so far, reacted easily with amines, sometimes selectively in the presence of water, leading to the corresponding amides. The results are rationalized by the involvement of the addition-elimination mechanism of phosphorylation with direct collapse of the primary zwitterionic intermediate formed by the amine attack on phosphorus.

Synthesis and in vitro antitumor activity of ring C and D-substituted phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine.

A series of cycle C and D-substituted phenanthrolin-7-ones, analogues of the marine pyridoacridines meridine and ascididemin have been synthesized on the basis of Diels-Alder reactions involving quinoline-5,8-dione and 2- (or un)-substituted-N,N-dimethylhydrazones. All the compounds were evaluated for in vitro cytotoxic activity against 12 distinct human cancer cell lines. They all exhibit cytotoxic activity with IC(50) values at least of micromolar order.

Synthesis and in vitro antitumor activity of phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine: structure-activity relationship.

A series of substituted pyrido[4,3,2-de][1,7] or [1,10]-phenanthrolin-7-ones, analogues of the marine pyridoacridines meridine and ascididemin, have been synthesized on the basis of Diels-Alder reactions involving different quinoline-5,8-diones and N,N-aldehyde-dimethylhydrazones. All the compounds were evaluated for in vitro cytotoxic activity against 12 distinct human cancer cell lines. They all exhibit cytotoxic activity with IC(50) values at least of micromolar order.