A consecutive Diels–Alder approach toward a Tet repressor directed combinatorial library

Diarylpropane‐1,3‐dione Derivatives as TetR‐Inducing Tetracycline Mimetics: Synthesis and Biological Investigations

“…Thus, we used an alternative route starting from 4-methoxy-3-nitrobenzoic acid (11), which was converted into the phenol ester 13. Treatment with KOtBu in DMF at 60 8C induced a Baker-Venkataraman rearrangement [18][19][20] in combination with the cleavage of the methyl ether to give the 1,3-diketone 15.…”

“…Thus, we reported a consecutive Diels-Alder approach towards a Tet-repressor directed combinatorial library of tc scaffold analogues. [11] As an extension of these studies, we now describe the synthesis, biological investigations and molecular docking studies of nonantibiotic and nontetracyclic inducers that feature a minimal key motif of the natural lead tc.…”

Combinatorial Chemistry Online Volume 8, Issue 8, August 2006

“…The synthesis was built on cross-conjugated trienes as central building blocks facilitating two consecutive cycloaddition processes with different dienophiles. 5 A library composed of a complete set of fucopyranosylgalactopyranosides has been synthesised. A perbenzylated phenylthio fucopyranoside and a series of tri-O-benzylgalactopyranosyl fluorides having single hydroxyl groups at the 2-, 3-, 4-, and 6-positions were used as the glycosyl donor and glycosyl acceptors, respectively.…”

Combinatorial Chemistry Online

“…However, a recent paper describes the use of consecutive Diels-Alder reactions in the synthesis of a library of tetracycline analogues investigated as potential binders to the tetracycline-inducible repressor protein, TetR. 1 The authors had created a mutant of TetR that displayed specificity for the tetracycline analogue (1). A solutionphase library approach was used to make a number of further analogues via a strategy that involved the use of crossconjugated trienes as central building blocks facilitating two consecutive cycloadditions with different dienophiles.…”

“…The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. 5 A facile method for the solid-phase synthesis of pyrrolo [2,1-c] [1,4]benzodiazepine dimers has been developed. p-Nitrophenyl carbonate Wang resin attached to 2-amino-5-methoxy-methyl benzoate has been utilised as the resin-bound starting material and these reactions were monitored by FT-IR spectroscopy of resin beads.…”