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Labelling of an anti-inflammatory agent with carbon-14, synthesis of 5-methoxy-2-methyl-1-(3,4-methylenedioxybenzoyl) indole-2-14C-3-acetic acid

✍ Scribed by Iwao Nakatsuka; Masaaki Hazue; Yoshiaki Makari; Kazuo Kawahara; Michio Endo; Akira Yoshitake

Publisher
John Wiley and Sons
Year
1976
Tongue
French
Weight
266 KB
Volume
12
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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