Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

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• Guarrochena, X.; Kanellopoulos, P.; Stingeder, A.; Rečnik, L.-M.; Feiner, I. V. J.; Brandt, M.; Kandioller, W.; Maina, T.; Nock, B. A.; Mindt, T. L. Amide-to-Triazole Switch in Somatostatin-14-Based Radioligands: Impact on Receptor Affinity and In Vivo Stability. Pharmaceutics 2024, 16, 392. doi:10.3390/pharmaceutics16030392
• Verena, A.; Merkens, H.; Chen, C.-C.; Chapple, D. E.; Wang, L.; Bendre, S.; Wong, A. A. W. L.; Bénard, F.; Lin, K.-S. Synthesis and Preclinical Evaluation of Two Novel 68Ga-Labeled Bispecific PSMA/FAP-Targeted Tracers with 2-Nal-Containing PSMA-Targeted Pharmacophore and Pyridine-Based FAP-Targeted Pharmacophore. Molecules (Basel, Switzerland) 2024, 29, 800. doi:10.3390/molecules29040800
• Li, W.; Yan, J.; Xu, W.; Zhang, L. Y. Magnetic nanoparticles modified with a copper(i) complex as a novel and efficient reusable catalyst for A3 coupling leading to C-N bond formation. RSC advances 2023, 13, 28964–28974. doi:10.1039/d3ra04871c
• Cimarelli, C.; Bacchiocchi, C.; Petroselli, M.; Lippolis, M.; Gentili, D.; Gabrielli, S. Diastereoselective Synthesis of Secondary Propargylamines Exploiting CuI-Based Promoters and Determination of Their Relative Configuration by DFT-GIAO Conformational Analysis. Synthesis 2022, 55, 1241–1252. doi:10.1055/a-1990-4867
• Bouvry, C.; Franzetti, M.; Cupif, J.-F.; Hurvois, J.-P. Total Synthesis of Phenanthropiperidine Alkaloids by Sequential Alkylation of N,N-Dibenzylaminoacetonitrile. European Journal of Organic Chemistry 2021, 2021, 6037–6051. doi:10.1002/ejoc.202101131
• Man, N.; Li, Y.; Jie, J.; Li, H.; Yang, H.; Zhao, Y.; Fu, H. Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N'-di-(tert-butoxycarbonyl)-aminals and β-Naphthols. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 12884–12889. doi:10.1002/chem.202102040
• Tonali, N.; Hericks, L.; Schröder, D. C.; Kracker, O.; Krzemieniecki, R.; Kaffy, J.; Le Joncour, V.; Laakkonen, P.; Marion, A.; Ongeri, S.; Dodero, V. I.; Sewald, N. Peptidotriazolamers Inhibit Aβ(1-42) Oligomerization and Cross a Blood-Brain-Barrier Model. ChemPlusChem 2021, 86, 840–851. doi:10.1002/cplu.202000814
• Ghosh, S. K.; Biswas, K. Metal-free multicomponent approach for the synthesis of propargylamine: a review. RSC advances 2021, 11, 2047–2065. doi:10.1039/d0ra09392k
• Stålsmeden, A. S.; Paterson, A. J.; Szigyártó, I. C.; Thunberg, L.; Johansson, J.; Beke-Somfai, T.; Kann, N. Chiral 1,5-disubstituted 1,2,3-triazoles - versatile tools for foldamers and peptidomimetic applications. Organic & biomolecular chemistry 2020, 18, 1957–1967. doi:10.1039/d0ob00168f
• Schröder, D. C.; Kracker, O.; Fröhr, T.; Góra, J.; Jewgiński, M.; Nieß, A.; Antes, I.; Latajka, R.; Marion, A.; Sewald, N. 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in chemistry 2019, 7, 155. doi:10.3389/fchem.2019.00155
• Kracker, O.; Góra, J.; Krzciuk-Gula, J.; Marion, A.; Neumann, B.; Stammler, H.-G.; Nieß, A.; Antes, I.; Latajka, R.; Sewald, N. 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 24, 953–961. doi:10.1002/chem.201704583
• Wünsch, M.; Senger, J.; Schultheisz, P.; Schwarzbich, S.; Schmidtkunz, K.; Michalek, C.; Klaß, M.; Goskowitz, S.; Borchert, P.; Praetorius, L.; Sippl, W.; Jung, M.; Sewald, N. Structure-Activity Relationship of Propargylamine-Based HDAC Inhibitors. ChemMedChem 2017, 12, 2044–2053. doi:10.1002/cmdc.201700550

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