Synthesis of novel indole derivatives containing amino acid

Indole, a benzopyrol, was first obtained from indigo by Adolf Von Baeyer in 1866. Indole is an aromatic heterocyclic organic compound with the formula C8H7N. Indole is widely distributed in natural environment and can be produced by a variety of bacteria. As an intercellular signaling molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, drug resistance and biofilm formation. The amino acid tryptophan is an indole derivative and precursor to the neurotransmitter serotonin. Although there is a lot of information about amino acid conjugates of indole-3-acetic acid in the literature, amino acid substituted derivatives in the homoaromatic ring of indole are not known. Therefore, the synthesis of new indole derivatives containing amino acids in the homoaromatic ring, which are not found in the literature, is aimed. Within the scope of this Master's thesis, ten new amino acid-indole conjugates were prepared by the reaction of protected amino acids with 5-aminomethylindole. Due to the structural similarity, six new amino acid-N-methyl-3-aminomethyl indole conjugates were also synthesized using N-methyl-3-aminomethylindole instead of 5-aminomethylindole. The structures of all synthesized compounds were identified by 1H-NMR, 13C-NMR, MS, FT-R spectroscopy and elemental analysis techniques. Keywords: Indole, Amino acid, Indole-amino acid conjugates