Arbeiten zur Synthese, Systematisierung und Nomenklatur von Schwefel-Stickstoff-Verbindungen sowie zur Synthese pharmakologisch interessanter Enzyminhibitoren
- Works on the synthesis, systematization and nomenclature of sulfur-nitrogen compounds and on the synthesis of pharmacologically interesting enzyme inhibitors
Bremerich, Maximilian; Bolm, Carsten (Thesis advisor); Niggemann, Meike (Thesis advisor)
Dissertation / PhD Thesis
Dissertation, RWTH Aachen University, 2020
The presented thesis is divided into six parts. In the first part, a novel systematization and nomenclature for organic sulfur-nitrogen compounds is proposed, which allows to identify hitherto unknown relationships between such compounds and could thus open up novel synthesis pathways. The second chapter describes the development of a synthesis of N- trityl-O-benzotriazolyl sulfonimidates from aromatic diazonium salts, N-hydroxybenzo- triazole as well as the novel NSO-template N-tritylsulfinylamine, and the reaction of these sulfonimidates with primary and secondary amines to the corresponding sulfonimidamides. Both reactions are characterized by broad applicability, tolerance to air and moisture and scalability. This methodology is applied in practice in chapter three to produce novel sulfonimidamide analogues of saccharin, sildenafil and ramatroban. In the fourth chapter, the production of sulfoximine analogues of the biomolecule sulforaphane is explained and a novel synthesis pathway is presented. Chapter five describes the total synthesis of three potential inhibitors of the enzyme TARG1. Finally, the last chapter summarizes attempts to synthesize a potential inhibitor of the nsP3 macrodomain of the Chikungunya virus.