Premium
2‐Anthracenonyl Acetic Acids as 5‐Lipoxygenase Inhibitors
Author(s) -
Prinz Helge,
Müller Klaus
Publication year - 1996
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19963290507
Subject(s) - chemistry , acetic acid , alkylation , derivative (finance) , carboxylic acid , glycolic acid , lipoxygenase , lactone , combinatorial chemistry , side chain , stereochemistry , organic chemistry , enzyme , catalysis , bacteria , lactic acid , polymer , biology , financial economics , economics , genetics
The synthesis of 2‐substituted anthracenonyl acetic acid (2‐AA) derivatives is described. The key step is the Marschalk reaction of 1‐hydroxy‐8‐methoxy‐anthracenedione with glycolic acid. After protection of the resulting 2‐anthracenonyl acetic acid derivative, the 2‐monoalkylated derivatives are selectively obtained by direct alkylation. The methodology proves quite general and allows for the introduction of various substituents onto the 2‐position of the carboxylic side chain. Reduction of the anthracenediones proceeds with concomitant protecting group removal and provides final 2‐AA products in good yields. The results of initial biological studies demonstrate enhanced 5‐lipoxygenase inhibition compared to anthralin.