Prodrugs of neuron-selective monoamine oxidase inhibitors: amino acid derivatives of 1-(4-aminophenyl)-2-aminopropanes

Synthesis of 4-Substituted 7-Azaindole Derivatives via Pd-Catalyzed C-N and C-O Coupling

“…The particularly electron-poor 2-fluoro-4-nitrophenol (5a) did not show any reaction (entries 10 and 11). Acetylated or Boc-protected p-aminophenols gave the products 6c and 6d in moderate yields (entries 12 and 13), while the more-electron-rich nucleophiles 5d-f furnished the desired ethers 6e-g in moderate and good yields, respectively (entries [14][15][16]. This seems to be consistent with literature presenting electron-rich phenols as favored substrates.…”

“…N 4 ,N 4 -Dibenzyl-2,6-difluorobenzene-1,4-diamine (2d) Ethyl [4-(dibenzylamino)-2,6-difluorophenyl]carbamate was prepared from N,N-dibenzyl-3,5-difluoroaniline 15 by carboxylation and subsequent Schmidt rearrangement following a procedure disclosed previously. 10 Ethyl [4-(dibenzylamino)-2,6-difluorophenyl]carbamate (2.10 g, 5.30 mmol) was dissolved in EtOH (40 mL).…”

Prodrugs for Amines

“…More recently, amino acids have been linked to anti-tumour amines to produce water-soluble amide prodrugs that release, in vivo , the parent amine [ 21 ]. Glycine and valine amides of monoaminooxidase A (MAO-A) inhibitors were also prepared as an attempt to deliver the active compounds to the brain before inhibiting MAO-A in the intestinal mucosa which leads to the potentiation of tyramine induced hypertension [ 22 ].…”