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Open AccessProceedings

Halogenated 2,1,3-benzoxadiazoles as Potential Fluorescent Warheads for Covalent Protease Inhibitors

1
National Research Tomsk Polytechnic University, 30 Lenin Ave., Tomsk 634050, Russia
2
Johannes Gutenberg-University Mainz Institute of Organic Chemistry, Duesbergweg 10-14, Mainz D-55128, Germany
*
Author to whom correspondence should be addressed.
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 54; https://doi.org/10.3390/ecsoc-22-05670
Published: 14 November 2018
Recently there has been a growing interest in covalent protease inhibitors in both industry and academia, caused by their longer residence times, their higher potency and their high ligand efficiency. Covalently reactive moieties which interact with activated amino acid residues such as serine or cysteine in enzymes like proteases or esterases mostly act through nucleophilic addition, substitution or ring opening. In contrast, nucleophilic aromatic substitution (SNAr) is rarely employed. In our previous work, we prepared and investigated electrophilic “warheads”, which contain aromatic, heteroaromatic or quinoid fragments. Some of them show potent inhibition constants for cathepsin L, cathepsin B, rhodesain or dengue-protease, and depending on the exact nature of the electrophile they exhibit reversible covalent or irreversible inhibition modes. In the present work, we demonstrate the synthesis of fluorescent “warhead” candidates based on 2,1,3-benzoxadiazoles and the investigation of their physicochemical and photophysical properties. These molecules shall serve as probes for the detailed analysis of association/dissociation mechanism and of the kinetic parameters of the bond forming event.
Keywords: 2,1,3-benzoxadiazoles; covalent protease inhibitors; fluorescentic properties 2,1,3-benzoxadiazoles; covalent protease inhibitors; fluorescentic properties
MDPI and ACS Style

Kuznetsova, A.; Klein, P.; Opatz, T. Halogenated 2,1,3-benzoxadiazoles as Potential Fluorescent Warheads for Covalent Protease Inhibitors. Proceedings 2019, 9, 54.

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