Synthesis of Acetaminophen Analogues Containing α-Amino Acids and Fatty Acids for Inhibiting Hepatotoxicity

Autor:	Nobuyuki Imai, Takuya Noguchi, Seunghee Jung, Yuya Kawashima
Rok vydání:	2019
Předmět:	chemistry.chemical_classification NAPQI Chemistry Organic Chemistry Imine Fatty acid Catalysis Acetaminophen Amino acid chemistry.chemical_compound Aniline AM404 medicine Organic chemistry Antipyretic medicine.drug
Zdroj:	Synthesis. 51:3683-3696
ISSN:	1437-210X 0039-7881
Popis:	Acetaminophen is a popular antipyretic analgesic medicine that has weaker anti-inflammatory properties and lower incidence of side effects than nonsteroidal anti-inflammatory drugs (NSAIDs). However, acetaminophen causes hepatotoxicity due to the reactive metabolite N-acetyl-p-benzoquinone imine (NAPQI). We have obtained acetaminophen analogues in 57–99% yields by using aniline derivatives with protected α-amino acids and fatty acids via the corresponding mixed carbonic carboxylic anhydrides in aqueous MeCN. We have also succeeded in synthesizing AM404 analogues in 76–97% yields, which are expected to be promising candidates for reducing hepatotoxicity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::045c2875a52c9f4431403255cb909145 https://doi.org/10.1055/s-0037-1611893 Zobrazit plný text záznamu