110417-52-2Relevant academic research and scientific papers
A PETERSON OLEFINATION REACTION USING SILYL-SUBSTITUTED SULFONAMIDE CARBANIONS. SYNTHESIS OF VINYLIC SULFONAMIDES
Mladenova, Margarita,Gaudemar-Bardone, Francoise
, p. 257 - 268 (2007/10/02)
α-Trimethylsilyl-substituted sulfonamides RCH(SiMe3)SO2N(CH3)2 (3), (R=H, CH3 and C6H5) are synthesized in almost quantitative yields.Their lithium derivatives 4 undergo a smooth Peterson olefination reaction with nonenolisable carbonyl compounds to give good to excellent yields of vinylsulfonamides 6.With R=H, the reaction is highly E-stereoselective.Moderate stereoselectivity is obtained in the cases of R=CH3, and R=C6H5.Key words: Peterson olefination reaction; N,N-dimethyl α-trimethylsilylsulfonamides; α-trimethylsilyl-substituted sulfonamide carbanions; vinylic sulfonamides; stereochemistry.
New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides
Brienne,Varech,Leclercq,Jacques,Radembino,Dessalles,Mahuzier,Gueyouche,Bories,Loiseau,Gayral
, p. 2232 - 2239 (2007/10/02)
Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinemia dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.
