Indoleacetic acid d(+) glucosamides - with anti-inflammatory activity

摘要

The D(+)-glucosamide (I) of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indoleacetic acid (II) is prepd. pref. by (a) reacting a soln. of an acid halide (pref. chloride) of (II), pref. in CHCl3, ether or dioxan, in the cold with an aqs. soln. of D(+)-glucosamine. HCl and an aqs. soln. of a strong base (pref. NaOH); or (b) ring closure of the N'-(p-chlorobenzoyl)-p-methoxyphenylhydrazone of N-levulinoyl-D(+)-glucosamine, pref. by heating in an org. solvent (esp. MeOH or HOAc) in the presence of an acid.