Histamine H3 receptor antagonists with peptidomimetic (keto)piperazine structures to inhibit Aβ oligomerisation

Zhang, 2021, Identification of N-phenyl-3-methoxy-4-pyridinones as orally bioavailable H3 receptor antagonists and β-amyloid aggregation inhibitors for the treatment of Alzheimer’s disease, Eur J Med Chem, 212, 10.1016/j.ejmech.2020.113096 Sharma, 2018, Comprehensive review of mechanisms of pathogenesis involved in Alzheimer’s disease and potential therapeutic strategies, Prog Neurobiol, 174, 53, 10.1016/j.pneurobio.2018.12.006 Marucci, 2020, Efficacy of acetylcholinesterase inhibitors in Alzheimer’s disease, J Neuropharm., 108352 Jończyk, 2019, Search for multifunctional agents against Alzheimer’s disease among non-imidazole histamine H3 receptor ligands. In vitro and in vivo pharmacological evaluation and computational studies of piperazine derivatives, Bioorg Chem, 90, 10.1016/j.bioorg.2019.103084 Cavazzoni, P. FDA’s Decision to Approve New Treatment for Alzheimer’s Disease | FDA. https://www.fda.gov/drugs/news-events-human-drugs/fdas-decision-approve-new-treatment-alzheimers-disease (2021). Ghamari, 2019, Histamine H3 receptor antagonists/inverse agonists: Where do they go?, Pharmacol Ther, 200, 69, 10.1016/j.pharmthera.2019.04.007 Bautista-Aguilera, 2017, Multitarget-Directed Ligands Combining Cholinesterase and Monoamine Oxidase Inhibition with Histamine H3R Antagonism for Neurodegenerative Diseases, Angew Chemie - Int Ed., 56, 12765, 10.1002/anie.201706072 Sadek, 2014, Non-imidazole histamine H3 receptor ligands incorporating antiepileptic moieties, Eur J Med Chem, 77, 269, 10.1016/j.ejmech.2014.03.014 Panula, 2015, International union of basic and clinical pharmacology XCVIII. histamine receptors, Pharmacol Rev, 67, 601, 10.1124/pr.114.010249 Sander, 2008, Histamine H3 Receptor Antagonists Go to Clinics, Biol Pharm Bull, 31, 2163, 10.1248/bpb.31.2163 Łażewska, 2018, Progress in the development of histamine H3 receptor antagonists/inverse agonists: a patent review (2013–2017), Expert Opin Ther Pat, 28, 175, 10.1080/13543776.2018.1424135 Trofimiuk, 2021, Selective H3 Antagonist (ABT-239) Differentially Modifies Cognitive Function Under the Impact of Restraint, Stress, 14, 1 Elmaleh, 2019, Developing Effective Alzheimer’s Disease Therapies: Clinical Experience and Future Directions, J. Alzheimer’s Dis., 71, 715, 10.3233/JAD-190507 Bonaventure, 2007, Histamine H3 receptor antagonists: From target identification to drug leads, Biochem Pharmacol, 73, 1084, 10.1016/j.bcp.2006.10.031 Savelieff, 2013, Untangling amyloid-beta, tau, and metals in Alzheimer’s disease, ACS Chem Biol, 8, 856, 10.1021/cb400080f Willbold, 2021, Amyloid-type Protein Aggregation and Prion-like Properties of Amyloids, Chem Rev, 10.1021/acs.chemrev.1c00196 Muralidar, 2020, Role of tau protein in Alzheimer’s disease: The prime pathological player, Int J Biol Macromol, 163, 1599, 10.1016/j.ijbiomac.2020.07.327 Abeysinghe, 2020, Alzheimer’s disease; a review of the pathophysiological basis and therapeutic interventions, Life Sci, 256, 10.1016/j.lfs.2020.117996 Tan, 2019, Emerging pathways to neurodegeneration: Dissecting the critical molecular mechanisms in Alzheimer’s disease, Parkinson’s disease Biomed Pharmacother, 111, 765, 10.1016/j.biopha.2018.12.101 Gulisano, 2018, Role of Amyloid-β and Tau Proteins in Alzheimer’s Disease: Confuting the Amyloid Cascade, J Alzheimer’s Dis, 64, S611, 10.3233/JAD-179935 Zhang, 2019, Toward the Mode of Action of the Clinical Stage All-d-Enantiomeric Peptide RD2 on Aβ42 Aggregation, ACS Chem Neurosci, 10, 4800, 10.1021/acschemneuro.9b00458 Klein, 2017, Optimization of d -Peptides for Aβ Monomer Binding Specificity Enhances Their Potential to Eliminate Toxic Aβ Oligomers, ACS Chem Neurosci, 8, 1889, 10.1021/acschemneuro.7b00045 Fillit, 2021, Aducanumab and the FDA — where are we now?, Nat Rev Neurol, 17, 129, 10.1038/s41582-020-00454-9 Khanfar, 2016, Multiple targeting approaches on histamine H3receptor antagonists, Front Neurosci, 10, 1, 10.3389/fnins.2016.00201 Agis-Torres, 2014, Multi-Target-Directed Ligands and other Therapeutic Strategies in the Search of a Real Solution for Alzheimer’s Disease, Curr Neuropharmacol, 12, 2, 10.2174/1570159X113116660047 Proschak, 2019, Polypharmacology by Design: A Medicinal Chemist’s Perspective on Multitargeting Compounds, J Med Chem, 62, 420, 10.1021/acs.jmedchem.8b00760 Schartmann, 2018, In vitro potency and preclinical pharmacokinetic comparison of all-d-enantiomeric peptides developed for the treatment of Alzheimer’s disease, J. Alzheimer’s Dis., 64, 859, 10.3233/JAD-180165 Jokar, 2020, Design of peptide-based inhibitor agent against amyloid-β aggregation : Molecular docking, synthesis and in vitro evaluation, Bioorg Chem, 102, 10.1016/j.bioorg.2020.104050 De, 2019, Destabilization of β-amyloid aggregates by thrombin derived peptide: plausible role of thrombin in neuroprotection, FEBS J Griner, 2019, Structure based inhibitors of amyloid beta core suggest a common interface with Tau, Elife, 8, 10.7554/eLife.46924 Borthwick, 2012, 2,5-diketopiperazines: Synthesis, reactions, medicinal chemistry, and bioactive natural products, Chem Rev, 112, 3641, 10.1021/cr200398y Bolognesi, 2010, Discovery of a class of diketopiperazines as antiprion compounds, ChemMedChem, 5, 1324, 10.1002/cmdc.201000133 Niida, 2006, Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-S N2′ reactions and their use in the preparation of low-molecule CXCR4 antagonists, J Org Chem, 71, 3942, 10.1021/jo060390t Jaunmuktane, 2020, Invited Review: The role of prion-like mechanisms in neurodegenerative diseases, Neuropathol Appl Neurobiol, 46, 522, 10.1111/nan.12592 Zhao, 2020, Cyclic dipeptides: Biological activities and self-assembled materials, Pept Sci To Evaluate the Safety, Tolerability and Pharmacokinetics of Oral NNZ-2591 in Healthy Volunteers. https://clinicaltrials.gov/ct2/show/NCT04379869?term=NNZ-2591.&draw=2&rank=1. Cornacchia, 2012, 2,5-Diketopiperazines as Neuroprotective Agents, Mini-Reviews Med Chem, 12, 2, 10.2174/138955712798868959 Szczepańska, 2020, Structural modifications in the distal, regulatory region of histamine H3 receptor antagonists leading to the identification of a potent anti-obesity agent, Eur J Med Chem Valeur, 2009, Amide bond formation: beyond the myth of coupling reagents, Chem Soc Rev, 38, 606, 10.1039/B701677H Schöllkopf, 1979, Enantioselektive Synthese von α-Methyl-α-amino-carbonsäuren durch Alkylierung des Lactimethers von cyclo-(L-Ala-L-Ala), Angew Chemie, 91, 922, 10.1002/ange.19790911110 González, 2004, Improvements in aldol reactions with diketopiperazines, Synth Commun, 34, 1589, 10.1081/SCC-120030746 Yamazaki, 2012, Synthesis and structure-activity relationship study of antimicrotubule agents phenylahistin derivatives with a didehydropiperazine-2,5-dione structure, J Med Chem, 55, 1056, 10.1021/jm2009088 Palladino, 2008, Analogs of dehydrophenylahistins and their theapeutic use, United States Pat., US2008/022 Fischer, 2003, Diketopiperazines in peptide and combinatorial chemistry, J Pept Sci, 9, 9, 10.1002/psc.446 Szczepanska, 2018, Histamine H3 Receptor Ligands in the Group of (Homo)piperazine Derivatives, Curr Med Chem, 25, 1609, 10.2174/0929867325666171123203550 Ziehm, 2018, Role of Hydrophobicity and Charge of Amyloid-Beta Oligomer Eliminating d -Peptides in the Interaction with Amyloid-Beta Monomers, ACS Chem Neurosci, 9, 2679, 10.1021/acschemneuro.8b00132 Müller-Schiffmann, 2010, Combining Independent Drug Classes into Superior, Synergistically Acting Hybrid Molecules, Angew Chemie Int Ed, 49, 8743, 10.1002/anie.201004437 Sander, 2010, Kojic Acid Derivatives as Histamine H3 Receptor Ligands, Chem Pharm Bull (Tokyo), 58, 1353, 10.1248/cpb.58.1353 Daniele, 2016, Lead Optimization of 2-Phenylindolylglyoxylyldipeptide Murine Double Minute (MDM)2/Translocator Protein (TSPO) Dual Inhibitors for the Treatment of Gliomas, J Med Chem, 59, 4526, 10.1021/acs.jmedchem.5b01767 Chambers, M. S. & et al. Bicyclic Heteroaryl-alkylene-(Homo)Piperazinones and Thione Analogues thereof, their preparation, and their use of as selective Agonists of 5HT1 like receptors. United States Pat. US00599841, (1991). Carter, D. S. & et al. Arylpiperazine derivatives and uses thereof. United States Pat. US2009/020, (2009). Crossland, 1970, A Facile Synthesis of Methanesulfonate Esters, J Org Chem, 35, 3195, 10.1021/jo00834a087 Best, 2004, Aryloxyalkylamine deivates as H3 receptor ligands, Int. Appl. Publ. Under Pat. Coop. Treaty WO2004/037 Kottke, 2011, Receptor-specific functional efficacies of alkyl imidazoles as dual histamine H3/H4 receptor ligands, Eur J Pharmacol, 654, 200, 10.1016/j.ejphar.2010.12.033 Yung-Chi, 1973, Relationship between the inhibition constant (KI) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction, Biochem Pharmacol, 22, 3099, 10.1016/0006-2952(73)90196-2 Bharatam, P. V. Drug Likeness Tool (DruLiTo 1). http://www.niper.gov.in/pi_dev_tools/DruLiToWeb/DruLiTo_index.html.