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@ARTICLE{Renk:891313,
      author       = {Renk, Dana R. and Skraban, Marcel and Bier, Dirk and
                      Schulze, Annette and Wabbals, Erika and Wedekind, Franziska
                      and Neumaier, Felix and Neumaier, Bernd and Holschbach,
                      Marcus},
      title        = {{D}esign, synthesis and biological evaluation of
                      {T}ozadenant analogues as adenosine {A}2{A} receptor
                      ligands},
      journal      = {European journal of medicinal chemistry},
      volume       = {214},
      issn         = {0223-5234},
      address      = {Amsterdam [u.a.]},
      publisher    = {Elsevier71544},
      reportid     = {FZJ-2021-01420},
      pages        = {113214},
      year         = {2021},
      abstract     = {With the aim to obtain potent adenosine A2A receptor (A2AR)
                      ligands, a series of eighteen derivatives of
                      4-hydroxy-N-(4-methoxy-7-morpholin-4-yl-1,3-benzo[d]thiazol-2-yl)-4-methylpiperidine-1-carboxamide
                      (SYN-115, Tozadenant) were designed and synthesized. The
                      target compounds were obtained by a chemical building block
                      principle that involved reaction of the appropriate
                      aminobenzothiazole phenyl carbamates with either
                      commercially available or readily synthesized functionalized
                      piperidines. Their affinity and subtype selectivity with
                      regard to human adenosine A1-and A2A receptors were
                      determined using radioligand binding assays. Ki values for
                      human A2AR ranged from 2.4 to 38 nM, with more than 120-fold
                      selectivity over A1 receptors for all evaluated compounds
                      except 13k which had a Ki of 361 nM and 18-fold selectivity.
                      The most potent fluorine-containing derivatives 13e, 13g and
                      13l exhibited Ki values of 4.9 nM, 3.6 nM and 2.8 nM for the
                      human A2AR. Interestingly, the corresponding values for rat
                      A2AR were found to be four to five times higher. Their
                      binding to A2AR was further confirmed by radiolabeling with
                      18F and in vitro autoradiography in rat brain slices, which
                      showed almost exclusive striatal binding and complete
                      displacement by the A2AR antagonist ZM 241385. We conclude
                      that these compounds represent potential candidates for the
                      visualization of the A2A receptor and open pathways to novel
                      therapeutic treatments of neurodegenerative disorders or
                      cancer.},
      cin          = {INM-5 / INM-2},
      ddc          = {610},
      cid          = {I:(DE-Juel1)INM-5-20090406 / I:(DE-Juel1)INM-2-20090406},
      pnm          = {525 - Decoding Brain Organization and Dysfunction
                      (POF4-525)},
      pid          = {G:(DE-HGF)POF4-525},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {33548636},
      UT           = {WOS:000629633800015},
      doi          = {10.1016/j.ejmech.2021.113214},
      url          = {https://juser.fz-juelich.de/record/891313},
}