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Original Research

Drug-likeness approach of 2-aminopyrimidines as histamine H3 receptor ligands

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Pages 1499-1513 | Published online: 19 Sep 2014

References

  • Arrang JM Garbarg M Schwartz JC Auto-inhibition of brain histamine release mediated by a novel class (H3) of histamine receptor Nature 1983 302 5911 832 837 6188956
  • Morisset S Rouleau A Ligneau X High constitutive activity of native H3 receptors regulates histamine neurons in brain Nature 2000 408 6814 860 864 11130725
  • Schlicker E Fink K Hinterthaner M Göthert M Inhibition of noradrenaline release in the rat brain cortex via presynaptic H3 receptors Naunyn-Schmiedebergs Arch Pharmacol 1989 340 6 633 638 2615855
  • Schlicker E Fink K Detzner M Göthert M Histamine inhibits dopamine release in the mouse striatum via presynaptic H3 receptors J Neural Transm Gen Sect 1993 93 1 1 10 8396945
  • Schlicker E Betz R Göthert M Histamine H3 receptor-mediated inhibition of serotonin release in the rat brain cortex Naunyn-Schmiedeberg’s Arch Pharmacol 1988 337 588 590 3412497
  • Sander K Kottke T Stark H Histamine H3 receptor antagonists go to clinics Biol Pharm Bull 2008 31 12 2163 2181 19043195
  • Gemkow MJ Davenport AJ Harich S Ellenbroek BA Cesura A Hallett D The histamine H3 receptor as a therapeutic drug target for CNS disorders Drug Discov Today 2009 14 9–10 509 515 19429511
  • Tiligada E Zampeli E Sander K Stark H Histamine H3 and H4 receptors as novel drug targets Expert Opin Investig Drugs 2009 18 10 1519 1531
  • Sadek B Schwed JS Subramanian D Non-imidazole histamine H3 receptor ligands incorporating antiepileptic moieties Eur J Med Chem 2014 77 269 279 24650714
  • de Esch IJ Thurmond RL Jongejan A Leurs R The histamine H4 receptor as a new therapeutic target for inflammation Trends Pharmacol Sci 2005 26 9 462 469 16054239
  • Więcek M Kottke T Ligneau X N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands Bioorg Med Chem 2011 19 9 2850 2858 21498080
  • Smits RA Leurs R de Esch IJ Major advances in the development of histamine H4 receptor ligands Drug Discov Today 2009 14 15–16 745 753 19477292
  • Sander K Kottke T Tanrikulu Y 2,4-Diaminopyrimidines as histamine H4 receptor ligands – Scaffold optimization and pharmacological characterization Bioorg Med Chem 2009 17 20 7186 96 19773175
  • Savall BM Chavez F Tays K Discovery and SAR of 6-Alkyl-2,4-diaminopyrimidines as histamine H4 receptor antagonists J Med Chem 2014 57 6 2429 2439 24495018
  • Lazewska D Kiec-Kononowicz K Azines as histamine H4 receptor antagonists Front Biosci (Schol Ed) 2012 1 4 967 987 22202103
  • Engelhardt H Schultes S de Graaf C Bispyrimidines as potent histamine H4 receptor ligands: delineation of structure-activity relationships and detailed H4 receptor binding mode J Med Chem 2013 56 11 4264 4276 23668417
  • Schreeb A Walter M Odadzic D Schwed JS Weizel L Stark H Piperazine modification in 2,4,6-triaminopyrimidine derivatives as histamine H4 receptor ligands Pharmazie 2013 6897 521 525 23923631
  • Schneider EH Schnell D Papa D Seifert R High constitutive activity and a G-protein-independent high-affinity state of the human histamine H4-receptor Biochemistry 2009 48 6 1424 1238 19166345
  • Kottke T Sander K Weizel L Schneider EH Seifert R Stark H Receptor-specific functional efficacies of alkyl imidazoles as dual histamine H3/H4 receptor ligands Eur J Pharmacol 2011 654 3 200 208 21237145
  • Isensee K Amon M Galaparti A Fluorinated non-imidazole histamine H3 receptor antagonists Bioorg Med Chem Lett 2009 19 8 2172 2175 19286376
  • Meier G Apelt J Reichert U Influence of imidazole replacement in different structural classes of histamine H3-receptor antagonists Eur J Pharm Sci 2001 13 3 249 259 11384847
  • Tomasch M Schwed JS Paulke A Stark H Bodilisant-a novel fluorescent, highly affine histamine H3 receptor ligand ACS Med Chem Lett 2013 4 2 269 273 24900647
  • Amon M Ligneau X Camelin JC Berrebi-Bertrand I Schwartz JC Stark H Highly potent fluorescence-tagged nonimidazole histamine H3 receptor ligands Chem Med Chem 2007 2 5 708 716 17361979
  • Williamson A About the theory of the formation of ethers Justus Liebigs Ann Chem 1851 77 37 49
  • Cheng YC Prusoff WH Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction Biochem Pharmacol 1973 22 23 3099 3108 4202581
  • Shultz MD Improving the plausibility of success with inefficient metrics ACS Med Chem Lett 2014 5 1 2 5 24900765
  • Polinsky A The Practice of Medicinal Chemistry 3rd ed Wermuth CG Elsevier Oxford 2008 19 244 254
  • Hopkins AL Keserü GM Leeson PD Rees DC Reynolds CH The role of ligand efficiency metrics in drug discovery Nat Rev Drug Discov 2014 13 2 105 121 24481311
  • Leeson PD Springthorpe B The influence of drug-like concepts on decision-making in medicinal chemistry Nat Rev Drug Discov 2007 6 11 881 890 17971784
  • Tarcsay A Nyíri K Keseru GM Impact of lipophilic efficiency on compound quality J Med Chem 2012 55 3 1252 1260 22229549
  • Abad-Zapatero C Ligand efficiency indices for effective drug discovery Expert Opin Drug Discov 2007 2 4 469 488 23484756
  • Lipinski CA Lombardo F Dominy BW Feeney PJ Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv Drug Deliv Rev 2001 46 1–3 3 26 11259830
  • Gad SC Preclinical Development Handbook: ADME and Biopharmaceutical Properties A John Wiley and Sons, Inc Hoboken, New Jersey 2008
  • Molinspiration software or free molecular property calculation services [last accessed June 07, 2013], [2 screens], Available from: http://www.molinspiration.com/cgi-bin/properties Accessed March 9, 2014
  • Odović J Marković B Vladimirov S Karljiković-Rajić K In vitro modeling of angiotensin-converting enzyme inhibitor’s absorption with chromatographic retention data and selected molecular descriptors J Chromatogr B Analyt Technol Biomed Life Sci 2014 15 953 954 102–107
  • Hopkins AL Groom CR Alex A Ligand efficiency: a useful metric for lead selection Drug Discov Today 2004 15 9 430 431 15109945
  • Meanwell NA Improving drug candidates by design: A focus on physicochemical properties as a means of improving compound disposition and safety Chem Res Toxicol 2011 24 9 1420 1456 21790149
  • Shultz MD The thermodynamic basis for the use of lipophilic efficiency (LipE) in enthalpic optimizations Bioorg Med Chem Lett 2013 23 21 5992 6000 24054120
  • Shultz MD Setting expectations in molecular optimizations: Strengths and limitations of commonly used composite parameters Bioorg Med Chem Lett 2013 23 21 5980 5991 24018190