Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for &beta;-Amyloid Plaques

Natural Products Synthesis & Bioorganic Chemistry Laboratory, Institute of Nanoscience & Nanotechnology, National Center for Scientific Research “Demokritos”, Patr. Grigoriou & Neapoleos 27, 153 41 Athens, Greece

Department of Chemistry, University of Patras, Rio Campus, Rio, 265 04 Patra, Greece

School of Health Sciences, Department of Pharmacy, Division of Pharmaceutical Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, 157 71 Athens, Greece

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Department of Food Science and Human Nutrition, Agricultural University of Athens, Iera Odos 75, 118 55 Athens, Greece

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Institute of Biosciences & Applications, National Center for Scientific Research “Demokritos”, Patr. Grigoriou & Neapoleos 27, 153 41 Athens, Greece

Authors to whom correspondence should be addressed.

Academic Editor: Ian R. Baxendale

Molbank 2022, 2022(1), M1343; https://doi.org/10.3390/M1343

Received: 23 January 2022 / Revised: 11 February 2022 / Accepted: 16 February 2022 / Published: 22 February 2022

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Abstract

Three novel pyrazolo[3,4-b]pyridines were synthesized via the cyclization of 5-amino-1-phenylpyrazole with the corresponding unsaturated ketone in the catalytic presence of ZrCl₄. The ketones were afforded by modifying a stabilized ylide facilitated Wittig reaction in fairly high yields. The novel compounds exhibited exciting photophysical properties with the dimethylamine phenyl-bearing pyrazolopyridine showing exceptionally large Stoke’s shifts. Finally, both the dimethylamino- and the pyrene-substituted compounds demonstrated high and selective binding to amyloid plaques of Alzheimer’s disease (AD) patient brain slices upon fluorescent confocal microscopy observation. These results reveal the potential application of pyrazolo[3,4-b]pyridines in the development of AD amyloid plaque probes of various modalities for AD diagnosis. View Full-Text

Keywords: pyrazolo[3,4-b]pyridines; β-amyloid plaque probes; AD diagnosis

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Vidali, V.P.; Nigianni, G.; Athanassopoulou, G.D.; Canko, A.; Mavroidi, B.; Matiadis, D.; Pelecanou, M.; Sagnou, M. Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques. Molbank 2022, 2022, M1343. https://doi.org/10.3390/M1343

AMA Style

Vidali VP, Nigianni G, Athanassopoulou GD, Canko A, Mavroidi B, Matiadis D, Pelecanou M, Sagnou M. Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques. Molbank. 2022; 2022(1):M1343. https://doi.org/10.3390/M1343

Chicago/Turabian Style

Vidali, Veroniki P., Georgia Nigianni, Georgia D. Athanassopoulou, Aleksander Canko, Barbara Mavroidi, Dimitris Matiadis, Maria Pelecanou, and Marina Sagnou. 2022. "Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques" Molbank 2022, no. 1: M1343. https://doi.org/10.3390/M1343

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Synthesis of Novel Pyrazolo[3,4-b]pyridines with Affinity for β-Amyloid Plaques

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