Synthesis and modifications of a small library of 1,4-benzodiazepin-3-ones toward potential inhibitors of the collagen—von Willebrand Factor interaction

A library of 1,4-benzodiazepin-3-one-based turn mimetics were synthesized and tested for their antithrombotic abilities. These mimetics are designed to incorporate amino acid side chains of the previously reported paratope of the inhibitory anti-von Willebrand Factor antibody 82D6A3. Modifications were performed on the scaffolds by alkylation of the N1-position and acylation of the reduced nitro group. Hereby the number of functional groups incorporated on the core was expanded.