Amino Acid Esters and Amides for Reductive Amination of Mucochloric Acid: Synthesis of Novel γ‐Lactams, Short Peptides and Antiseizure Agent Levetiracetam (Keppra^®)

Abstract

A simple methodology utilizing mucochloric acid and different α-and β-amino acid esters, amides and short peptides for the synthesis of novel γ-lactam and γ-lactambased short peptides was developed. The synthesis of an

Automated three-component synthesis of a library of γ-lactams

“…Compounds containing a γ-lactam moiety have been significant in the treatment of epilepsy [6–7], HIV [8–9], neurodegenerative disease and depression [10–11]. Having identified the lactam ring as a target of opportunity in chemical-screening efforts, we previously reported a method to prepare γ-lactams from readily available maleimides, aldehydes and amines [12].…”

Reinvestigation of Mucohalic Acids: Recent Development and Application in Drug Discovery

“…一般而言, 在糠氯酸的还原胺化反应中, 芳香胺、 苄胺、以及烷基胺、氨基酸酯和手性胺都能用于 γ-酰胺 的形成 [33,34] (Scheme 6). 优化的实验也表明, 4 Å 分子筛 能有效地除去环合反应中形成的水, 进而有效地提高产 率.…”

“…优化的实验也表明, 4 Å 分子筛 能有效地除去环合反应中形成的水, 进而有效地提高产 率. 我们还成功地利用这一关键反应, 仅用三步反应就 制备 UCB 的癫痫症治疗药物左乙拉西坦 Keppra [34] (Scheme 7). [35] .…”

Genotoxic halofuranones in water: isomerization and acidity of mucohalic acids

“…In recent years, MXA have also attracted much attention in organic synthesis owing to their high functionalization and availability, and they have been used in the synthesis of heterocycles such as gamma‐substituted gamma‐butenolides and gamma‐lactams, and other furanone derivatives 23–35…”