Synthesis and biological evaluation of 1,4-benzodiazepin-2-ones with antitrypanosomal activity

MAOS and Medicinal Chemistry: Some Important Examples from the Last Years

“…Microwave synthesis was used in order to create the N -benzyl series of analogues that presented moderated activity against trypanosomes [ 85 ]. The nitro compounds 45 was exploited as precursor of the corresponding anilines 46 , in yields ranging from 74 to 99%, by using molybdenum hexacarbonyl and DBU at 150 °C in a sealed tube for 15 min under microwave irradiation [ 86 , 87 ].…”

Synthesis and biological evaluation of benzodiazepines containing a pentafluorosulfanyl group

“…With research outputs in both benzodiazepine [16,17] and SF5 chemistry [18] , there was a natural inclination for us to combine these interests in the design of SF5containing BZDs. We, therefore, aimed to synthesise analogues 2a -2c (Scheme 1) related to the much-prescribed drug, diazepam (Valium TM ) in order to evaluate the effect of changing a Cl for a SF5 group on biological activity.…”

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

“…The 1,4-benzodiazepine scaffold is a well-established “privileged scaffold” in medicinal chemistry, − and we have an active interest in synthesizing libraries of such compounds. − Our recently described triazolo-benzodiazepine derivative TC AC 28 is a potent, selective bromo and extraterminal bromodomain inhibitor and a useful epigenetic tool compound, with a crystallographically defined binding mode to the target protein and displaying K d values of 40 and 800 nM toward Brd2(2) and Brd2(1), respectively. , We sought to scale up the original seven-step-protocol toward the racemic product (as in the original manuscript) with the aim of improving the final two problematic and low-yielding steps …”