| Summary: | In this thesis the successful synthesis of a novel tricyclic scaffold containing a ring fused triazole and piperidine will be discussed and furthermore its utility as a new potential privileged structure will be evaluated.
As starting material for the synthesis of the considered scaffolds the commercially available ethyl 4-oxopiperidine-1-carboxylate 108 was used. Piperidone 108 was converted into scaffolds 96, 97 and 98 alternating the ring size (n=1, 2, 3) of the fused bicyclic ring. This tricyclic triazole scaffold was incorporated into known biologically active molecules (Sitaglitpin, a DPP-4 inhibitor; Maraviroc, a CCR-5 receptor antagonist and GDC-0941, a pi3K inhibitor) to test its potential to serve as a new possible Privileged Scaffold. Through scaffold hopping, analogues with excellent biological activity against the chosen biological targets were achieved.
Additionally, the stereoselective synthesis of one of the four possible isomers of the tricyclic triazole 178 was obtained in 4 steps to give the synthetically access towards the synthesis of all feasible enantiomeric and diastereomeric analogues.
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