Stereocontrolled synthesis of anticancer beta-lactams via the Staudinger reaction.
Stereocontrolled synthesis of novel beta-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-beta-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-beta-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting beta-lactams. SAR has identified beta-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.
Banik
Bimal K
BK
Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, USA. banik@panam.edu
Banik
Indrani
I
Becker
Frederick F
FF
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D000970:Antineoplastic Agents; D007097:Imines; D047090:beta-Lactams