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Communication

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

1
Natural Products Synthesis & Bioorganic Chemistry Laboratory, Institute of Nanoscience & Nanotechnology, National Center for Scientific Research “Demokritos”, Patr. Grigoriou & Neapoleos 27, 153 41 Athens, Greece
2
Department of Chemistry, University of Patras, Rio Campus, Rio, 265 04 Patra, Greece
3
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
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 pyrazolo[3,4-b]pyridines; β-amyloid plaque probes; AD diagnosis
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MDPI and ACS Style

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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