An Improved Synthesis of Isonitrosoacetanilides.

Rewcastle, Gordon W.; Sutherland, Hamish S.; Weir, Claudette A.; Blackburn, Adrian G.; Denny, William A.

doi:10.1002/chin.200611083

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“…28 Thus, the methylnitroanilines 6 and 14 were converted into isatins 8 and 16 using a recent modification of the isonitrosoacetanilide Sandmeyer procedure. 29 Oxidation to the anthranilic acids 9 and 17 followed by diazotization and reaction with KI gave iodides 10 and 18. The potassium salt of these acids reacted with the disodium salt of 2-hydroxyphenylacetic acid under TDA-1 catalysis to give the diphenyl ethers 11 and 19, which were cyclized to give the xanthenones 12 and 20 using 85% H 2 SO 4 .…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Biological Activity of Azido Analogues of 5,6-Dimethylxanthenone-4-acetic Acid for Use in Photoaffinity Labeling

et al. 2007

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5,6-Dimethylxanthenone-4-acetic acid (1) is scheduled for phase III clinical trials as a vascular disrupting agent. However, its biochemical receptor(s) have yet to be identified. In this report, the synthesis of azido analogues of 1 that could be used for photoaffinity labeling of proteins as an approach toward identifying its molecular targets is described. While 5-azidoxanthenone-4-acetic acid (2) and 5-azido-6-methylxantheone-4-acetic acid (3) were found to have biological activities similar to that of 1, 6-azido-5-methylxanthenone-4-acetic acid (4) was unstable and could not be evaluated. Both azido compounds 2 and 3 activated NF-kappaB, induced the production of tumor necrosis factor in cultured mouse splenocytes, and induced hemorrhagic necrosis of colon 38 tumors in mice. Photoreaction of lysates from spleen cells with tritiated 2 resulted in two radiolabeled protein bands at 50 and 14 kDa that could be competitively inhibited with cold 1 and cold 2. The azido compounds 2 and 3 exhibit all the requirements for use in photoaffinity labeling of potential receptor(s) for 1.

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Section: Chemistrymentioning

confidence: 99%