Efficient synthesis of pharmaceutical organic compounds using heteroaromatic reagents

The thesis is presented in 4 chapters:Chapter 1: The chemical similarity of antibacterial cyclic peptides andpeptidomimetics was studied in order to identify new promising cyclic scaffolds. Alarge descriptor space coupled with cluster analysis was employed to digitize knownantibacterial structures and to gauge the potential of new peptidomimeticmacrocycles, which were conveniently synthesized by acylbenzotriazolemethodology. Some of the synthesized compounds were tested against an array ofmicroorganisms and showed antibacterial activity against Bordetellabronchistepica, Micrococcus luteus, and Salmonella typhimurium.Chapter 2: Optimized selective S-acylations of cysteine esters gaveintermediates for the synthesis of macrocyclic peptoids via benzotriazolemethodology.Chapter 3: Nα-Boc-Nim-4-toluenesulfonyl-L-histidinoylbenzotriazole enablesconvenient acylation of N-, O- , S- and C- nucleophiles with no detectableracemization. We report efficient syntheses of novel histidine-containing di-, tri-,and tetra-peptides and models for the preparation of potentially biologically activehistidine N-, O- , S- and C- conjugates.Chapter 4: Amino acid and peptide conjugates of quinine were synthesizedin 52-95% yields using benzotriazole methodology under microwave irradiation.