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An improved synthesis of 5,6-dimethylxanthenone-4-acetic acid (DMXAA).

Abstract：

:5,6-Dimethylxanthenone-4-acetic acid (DMXAA) is a novel anticancer agent with a number of unique activities, and is in clinical trial. The current synthesis of DMXAA involves six steps, beginning with a heterogeneous reaction to form an isonitrosoacetanilide, and gives an overall yield of 11% from 2,3-dimethylaniline. We report an alternative synthesis of the key intermediate 3,4-dimethylanthranilic acid via nitration of 3,4-dimethylbenzoic acid and separation of the key desired isomer by ready crystallisation. This, together with improvements in the rest of the synthesis, provide a shorter and higher-yielding route to DMXAA (22% overall from 3,4-dimethylbenzoic acid).

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Atwell GJ,Yang S,Denny WA

doi

10.1016/s0223-5234(02)01406-x

subject

Has Abstract

pub_date

2002-10-01 00:00:00

pages

825-8

issue

10

eissn

0223-5234

issn

1768-3254

pii

S022352340201406X

journal_volume

37

pub_type

杂志文章

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