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@ARTICLE{Drerup:824107,
      author       = {Drerup, Christian and Ermert, Johannes and Coenen, Heinrich
                      Hubert},
      title        = {{S}ynthesis of a {P}otent {A}minopyridine-{B}ased
                      n{NOS}-{I}nhibitor by {T}wo {R}ecent {N}o-{C}arrier-{A}dded
                      $^{18}${F}-{L}abelling {M}ethods},
      journal      = {Molecules},
      volume       = {21},
      number       = {9},
      issn         = {1420-3049},
      address      = {Basel},
      publisher    = {MDPI75390},
      reportid     = {FZJ-2016-06731},
      pages        = {1160 -},
      year         = {2016},
      abstract     = {Nitric oxide (NO), an important multifunctional signaling
                      molecule, is produced by threeisoforms of NO-synthase (NOS)
                      and has been associated with neurodegenerative disorders.
                      Selectiveinhibitors of the subtypes iNOS (inducible) or nNOS
                      (neuronal) are of great interest for
                      decodingneurodestructive key factors, and 18F-labelled
                      analogues would allow investigating the NOS-functionby
                      molecular imaging with positron emission tomography.
                      Especially, the highly selective nNOSinhibitor
                      6-((3-((3-fluorophenethylamino)methyl)phenoxy)methyl)-4-methylpyridin-2-amine
                      (10)lends itself as suitable compound to be 18F-labelled in
                      no-carrier-added (n.c.a.) form. For preparationof the
                      18F-labelled nNOS-Inhibitor [18F]10 a “build-up”
                      radiosynthesis was developed based on acorresponding
                      iodonium ylide as labelling precursor. The such activated
                      phenethyl group of thecompound was efficiently and
                      regioselectively labelled with n.c.a. [18F]fluoride in
                      $79\%$ radiochemicalyield (RCY). After conversion by
                      reductive amination and microwave assisted displacement of
                      theprotecting groups, the desired nNOS-inhibitor was
                      obtained in about $15\%$ total RCY. Alternatively,for a
                      simplified “late-stage” 18F-labelling procedure a
                      corresponding boronic ester precursor wassynthesized and
                      successfully used in a newer, copper(II) mediated n.c.a.
                      18F-fluoro-deboroniationreaction, achieving the same total
                      RCY. Thus, both methods proved comparatively suited to
                      providethe highly selective NOS-inhibitor [18F]10 as probe
                      for preclinical in vivo studies.},
      cin          = {INM-5},
      ddc          = {540},
      cid          = {I:(DE-Juel1)INM-5-20090406},
      pnm          = {573 - Neuroimaging (POF3-573)},
      pid          = {G:(DE-HGF)POF3-573},
      typ          = {PUB:(DE-HGF)16},
      UT           = {WOS:000385479800057},
      pubmed       = {27598109},
      doi          = {10.3390/molecules21091160},
      url          = {https://juser.fz-juelich.de/record/824107},
}