With four imidazopyridine-containing drugs and one pyrazolopyridine-containing drug on the market, bicyclic pyridines containing ring-junction nitrogen are privileged structures in medicinal chemistry. With two nitrogen atoms with potential to serve as hydrogen bond acceptors, imidazopyridines and pyrazolopyridines may boost binding to target proteins and elevate potency. In addition, these structures have found utility in FBDD, covalent inhibitors, reducing metabolic liabilities, and creating novel chemical space and intellectual properties. With many of the advanced intermediates now commercially available, they will find more and more applications in drug discovery.
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The two N atoms in Benzothiadiazole could possibly form intermolecular hydrogen bonding, leading to a more planar backbone. Benzothiadiazole is a strong electron-accepting molecular fragment. By fusing it with thiazole donor-acceptor dyes, near-infrared fluorescence was created. The benzothiadiazole ring is a useful n-type building block for designing electron-transport materials for organic and polymer light-emitting diodes (LEDs). Arene- and heteroarene-fused thiadiazoles have also found use in the design of low-band-gap materials for the construction of organic field-effect transmitters (OFETs), as stable organic radicals, and as one or two photon-absorbing materials for the design of nonlinear near-infrared (NIR) dyes. Benzothiadiazoles acting as the electron-accepting cores have been incorporated into dendrimer-type light-harvesting materials.
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