488829-87-4Relevant academic research and scientific papers
Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
Banik, Bimal K.,Banik, Indrani,Becker, Frederick F.
, p. 3611 - 3622 (2007/10/03)
Stereocontrolled synthesis of novel β-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-β-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-β-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting β-lactams. SAR has identified β-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.
