Sylvain Pellegrini

One-pot microwave-assisted synthesis and antimalarial activity of ferrocenyl benzodiazepines

An efficient synthesis of 1,4-benzodiazepin-2-ones is described by condensation between 2-aminobenzophenone and Boc-protected amino acids via microwave-assisted irradiation. This produces higher yields in shorter reaction times than with traditional methods. The antiplasmodial activity of the corresponding ferrocenyl benzodiazepines was evaluated in vitro against Plasmodium falciparum F32 (chloroquine-sensitive) and FCB1 and K1 (chloroquine-resistant) strains and gabonese clinical isolates.

Synthesis and biological activity of ferrocenyl indeno[1,2-c]isoquinolines as topoisomerase II inhibitors

Three series of indeno[1,2-c]isoquinolines bearing a ferrocenyl entity were synthesized and evaluated for DNA interaction, topoisomerase I and II inhibition, and cytotoxicity against breast human cancer cell lines. In the first and second series, the ferrocenyl scaffold was inserted as a linker between the two nitrogen atoms. In the last series, it was introduced at the end of the carbon chain. The present study showed that the ferrocenyl entity enhanced the topoisomerase II inhibition. Most compounds showed a potent growth inhibitory effect on MDA-MB-231 cell line with the IC50 in μM range.

In situ generation of dihydropyridine for the enantioselective transfer hydrogenation of 1,4-benzoxazines

A new strategy for the enantioselective transfer hydrogenation of benzoxazines involving an in situ generation of Hantzsch ester has been developed. Dihydroadducts were isolated in good yields (75–99%) and enantioselectivities (89–96% ee).

Synthesis and in vitro antiplasmodial activity of ferrocenyl aminoquinoline derivatives

The aim of this study was to synthesize a series of ferrocenyl 4-aminoquinolines and to evaluate their activities against Plasmodium falciparum F32 (chloroquine-sensitive) and FCB1 and K1 (chloroquino-resistant). Some of the ferrocenyl compounds exhibited in vitro antiplasmodial activity in the nM range. In particular, (1R,4R)-N1-(7-chloroquinolin-4-yl)-N4-(ferrocenylmethyl)-N4-methylcyclohexane-1,4-diamine 17 presented the lowest IC50 value (26 nM) against CQ-resistant strains.

In situ generation of ammonia for the copper-catalyzed synthesis of primary aminoquinolines

The synthesis of primary aminoquinolines from iodoquinolines was carried out in the presence of copper(I) iodide and formamide as the solvent and source of ammonia generated in situ. The reaction proceeded under mild conditions within a few hours and was applicable to various iodoquinolines.

Catalytic one-pot microwave assisted synthesis of 4-azapodophyllotoxin derivatives and rational design of experiment

A catalytic one-pot microwave assisted synthesis of 4-azapodophyllotoxin has been described. Rational design of experiment has been used to obtain the reaction yield.

Enantioselective transfer hydrogenation, a key step for the synthesis of 3-aminotetrahydroquinolines

An enantioselective transfer hydrogenation has been successfully achieved to furnish 3-aminotetrahydroquinolines. The reaction was conducted in the presence of Hantzsch dihydropyridine and a catalytic amount of chiral phosphoric acid under mild conditions.