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Labelling of an anti‐inflammatory agent with carbon‐14, synthesis of 5‐methoxy‐2‐methyl‐1‐(3,4‐methylenedioxybenzoyl) indole‐2‐ 14 C‐3‐acetic acid
Author(s) -
Nakatsuka Iwao,
Hazue Masaaki,
Makari Yoshiaki,
Kawahara Kazuo,
Endo Michio,
Yoshitake Akira
Publication year - 1976
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580120309
Subject(s) - chemistry , levulinic acid , yield (engineering) , acetic acid , decarboxylation , hydrochloric acid , carbon 14 , indole test , sodium hydroxide , ethyl bromoacetate , labelling , sodium acetate , organic chemistry , medicinal chemistry , nuclear chemistry , catalysis , biochemistry , materials science , physics , quantum mechanics , metallurgy
5‐Methoxy‐2‐methyl‐1‐(3,4‐methylenedioxybenzoyl)indole‐3‐acetic acid (ID‐955)(I), a new anti‐inflammatory agent, was labelled with carbon‐14 at C‐2 position of indole nucleus for the use of metabolic studies. The procedure used is shown in Fig. 1 and 2. Levulinic‐4‐ 14 C acid was synthesized in 57% yield by condensation of ethyl acetoacetate‐3‐ 14 C with ethyl bromoacetate and subsequent decarboxylation with hydrochloric acid. Reaction of III with N 1 ‐(3,4‐methylenedioxybenzoyl)‐4‐methoxyphenylhydrazine (II) gave ID‐955‐2‐ 14 C (I) in 58% yield. A total of 10.6 mCi of pure ID‐955‐2‐ 14 c (I) was obtained, representing 25% radiochemical yield from sodium acetate‐1‐ 14 C.