Gram-Scale Laboratory Synthesis of TC AC 28, a High-Affinity BET Bromodomain Ligand

  • ACS Omega. 2017 Aug 8;2(8):4328-4332. doi: 10.1021/acsomega.7b00780.
Raysa Khan  1 ,  Graham Marsh  2 ,  Robert Felix  2 ,  Paul D Kemmitt  3 ,  Matthias G J Baud  4 ,  Alessio Ciulli  4 ,  John Spencer  1
Affiliations
  • 1. Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton BN1 9QJ, U.K.
  • 2. Tocris Bioscience, the Watkins Building, Atlantic Road, Avonmouth, Bristol BS11 9QD, U.K.
  • 3. Oncology, AstraZeneca, 310 Cambridge Science Park, Milton Road, Cambridge CB4 0WG, U.K.
  • 4. Division of Biological Chemistry and Drug Discovery, School of Life Sciences, University of Dundee, James Black Centre, Dow Street, Dundee DD1 5EH, U.K.
PMID: 31457724 DOI: 10.1021/acsomega.7b00780
Abstract

TC AC 28, 6-(1H-Indol-4-yl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-4-acetic acid methyl ester, has been synthesized on a near-gram scale in seven steps with notable improvements in the reported poor-yielding last two steps enabling this key chemical probe compound to be available for researchers.

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