184166-96-9Relevant academic research and scientific papers
Synthesis of complex δ-acetylenic amino acids as potential multisubstrate adduct inhibitors of methyltransferases
Burns, Mark R.,Coward, James K.
, p. 1455 - 1470 (2007/10/03)
The synthesis of two types of δ-acetylenic amino acids is described. Key intermediates were derived from terminal acetylenes via two different routes: (1) palladium-mediated, Heck-type arylation, and (2) Simmons-Smith homologation followed by reaction of the resulting propargylic organometallic with a benzoyltrimethylsilane. Further elaboration to the desired amino acids involved the coupling of carbanions derived from N-benzylidene glycine esters to complex alkyl halides. The synthesis of nonnucleoside δ-acetylenic amino acids was successfully effected using this chemistry. In the case of the nucleoside-containing amino acids, a potential multisubstrate adduct: inhibitor of catechol O-methyltransferase was synthesized via this route. Unfortunately, the sensitivity to acid of 5'-deoxy, 5'-carbanucleosides prevented successful completion of the synthesis of a second nucleoside-containing δ-amino acid as a possible inhibitor of phenethanolamine N-methyltransferase.
