Literature DB >> 20801028

Synthesis and evaluation of 1,2,4-triazolo[1,5-c]pyrimidine derivatives as A2A receptor-selective antagonists.

Bidhan A Shinkre1, T Santhosh Kumar, Zhan-Guo Gao, Francesca Deflorian, Kenneth A Jacobson, William C Trenkle.   

Abstract

Movement disorders such as Parkinson's disease and Huntington's disease are serious life-limiting and debilitating movement disorders. Their onset typically occurs from mid-life to late in life, and effective diagnostic techniques for detecting and following the disease course are lacking. Our goal is to develop receptor imaging agents for positron emission tomography (PET) that selectively target the most relevant subtype of adenosine receptors (AR) that are highly expressed in the striatum, that is, the A(2A) AR. To further this goal, we have synthesized and characterized pharmacologically a family of high affinity A(2A) AR ligands, based on the known antagonist, SCH 442416 (R=-Me), which have structural variability on the terminus (R=-Et, -i-Pr, -allyl, and others). A O-fluoroethyl analogue suitable for use as a PET tracer had a K(i) value of 12.4 nM and was highly selective for the A(2A) AR in comparison to the A(1) and A(3) ARs. Published by Elsevier Ltd.

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Year:  2010        PMID： 20801028      PMCID： PMC2946083          DOI： 10.1016/j.bmcl.2010.08.021

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  18 in total

1.  Design, radiosynthesis, and biodistribution of a new potent and selective ligand for in vivo imaging of the adenosine A(2A) receptor system using positron emission tomography.

Authors:  S Todde; R M Moresco; P Simonelli; P G Baraldi; B Cacciari; G Spalluto; K Varani; A Monopoli; M Matarrese; A Carpinelli; F Magni; M G Kienle; F Fazio
Journal:  J Med Chem       Date:  2000-11-16       Impact factor: 7.446

2.  Novel Alexa Fluor-488 labeled antagonist of the A(2A) adenosine receptor: Application to a fluorescence polarization-based receptor binding assay.

Authors:  Miklós Kecskés; T Santhosh Kumar; Lena Yoo; Zhan-Guo Gao; Kenneth A Jacobson
Journal:  Biochem Pharmacol       Date:  2010-05-11       Impact factor: 5.858

3.  A novel gene containing a trinucleotide repeat that is expanded and unstable on Huntington's disease chromosomes. The Huntington's Disease Collaborative Research Group.

Authors: 
Journal:  Cell       Date:  1993-03-26       Impact factor: 41.582

4.  Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3'-azido-3'-deoxythymidine.

Authors:  A Tsotinis; T Calogeropoulou; M Koufaki; C Souli; J Balzarini; E De Clercq; A Makriyannis
Journal:  J Med Chem       Date:  1996-08-16       Impact factor: 7.446

5.  2-Chloro-N6-[3H]cyclopentyladenosine ([3H]CCPA)--a high affinity agonist radioligand for A1 adenosine receptors.

Authors:  K N Klotz; M J Lohse; U Schwabe; G Cristalli; S Vittori; M Grifantini
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1989-12       Impact factor: 3.000

6.  [3H]CGS 21680, a selective A2 adenosine receptor agonist directly labels A2 receptors in rat brain.

Authors:  M F Jarvis; R Schulz; A J Hutchison; U H Do; M A Sills; M Williams
Journal:  J Pharmacol Exp Ther       Date:  1989-12       Impact factor: 4.030

7.  Design, synthesis, and biological evaluation of a second generation of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines as potent and selective A2A adenosine receptor antagonists.

Authors:  P G Baraldi; B Cacciari; G Spalluto; M Bergonzoni; S Dionisotti; E Ongini; K Varani; P A Borea
Journal:  J Med Chem       Date:  1998-06-04       Impact factor: 7.446

8.  125I-4-aminobenzyl-5'-N-methylcarboxamidoadenosine, a high affinity radioligand for the rat A3 adenosine receptor.

Authors:  M E Olah; C Gallo-Rodriguez; K A Jacobson; G L Stiles
Journal:  Mol Pharmacol       Date:  1994-05       Impact factor: 4.436

9.  125I-4-(2-[7-amino-2-[2-furyl][1,2,4]triazolo[2,3-a][1,3,5] triazin-5-yl-amino]ethyl)phenol, a high affinity antagonist radioligand selective for the A2a adenosine receptor.

Authors:  T M Palmer; S M Poucher; K A Jacobson; G L Stiles
Journal:  Mol Pharmacol       Date:  1995-12       Impact factor: 4.436

10.  In vivo imaging of adenosine A2A receptors in rat and primate brain using [11C]SCH442416.

Authors:  R M Moresco; S Todde; S Belloli; P Simonelli; A Panzacchi; M Rigamonti; M Galli-Kienle; F Fazio
Journal:  Eur J Nucl Med Mol Imaging       Date:  2004-11-10       Impact factor: 9.236
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  8 in total

1.  Molecular probes for the A2A adenosine receptor based on a pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine scaffold.

Authors:  T Santhosh Kumar; Shilpi Mishra; Francesca Deflorian; Lena S Yoo; Khai Phan; Miklos Kecskés; Angela Szabo; Bidhan Shinkre; Zhan-Guo Gao; William Trenkle; Kenneth A Jacobson
Journal:  Bioorg Med Chem Lett       Date:  2010-11-21       Impact factor: 2.823

2.  The Concise Guide to PHARMACOLOGY 2013/14: G protein-coupled receptors.

Authors:  Stephen P H Alexander; Helen E Benson; Elena Faccenda; Adam J Pawson; Joanna L Sharman; Michael Spedding; John A Peters; Anthony J Harmar
Journal:  Br J Pharmacol       Date:  2013-12       Impact factor: 8.739

3.  Reinterpreting anomalous competitive binding experiments within G protein-coupled receptor homodimers using a dimer receptor model.

Authors:  Verònica Casadó-Anguera; Estefanía Moreno; Josefa Mallol; Sergi Ferré; Enric I Canela; Antoni Cortés; Vicent Casadó
Journal:  Pharmacol Res       Date:  2018-11-22       Impact factor: 7.658

4.  Striatal adenosine A(2A) receptor-mediated positron emission tomographic imaging in 6-hydroxydopamine-lesioned rats using [(18)F]-MRS5425.

Authors:  Abesh Kumar Bhattacharjee; Lixin Lang; Orit Jacobson; Bidhan Shinkre; Ying Ma; Gang Niu; William C Trenkle; Kenneth A Jacobson; Xiaoyuan Chen; Dale O Kiesewetter
Journal:  Nucl Med Biol       Date:  2011-03-30       Impact factor: 2.408

5.  Quantitation of the A2A Adenosine Receptor Density in the Striatum of Mice and Pigs with [18F]FLUDA by Positron Emission Tomography.

Authors:  Daniel Gündel; Magali Toussaint; Thu Hang Lai; Winnie Deuther-Conrad; Paul Cumming; Susann Schröder; Rodrigo Teodoro; Rareş-Petru Moldovan; Francisco Pan-Montojo; Bernhard Sattler; Klaus Kopka; Osama Sabri; Peter Brust
Journal:  Pharmaceuticals (Basel)       Date:  2022-04-22

6.  PET Imaging of the Adenosine A2A Receptor in the Rotenone-Based Mouse Model of Parkinson's Disease with [18F]FESCH Synthesized by a Simplified Two-Step One-Pot Radiolabeling Strategy.

Authors:  Susann Schröder; Thu Hang Lai; Magali Toussaint; Mathias Kranz; Alexandra Chovsepian; Qi Shang; Sladjana Dukić-Stefanović; Winnie Deuther-Conrad; Rodrigo Teodoro; Barbara Wenzel; Rareş-Petru Moldovan; Francisco Pan-Montojo; Peter Brust
Journal:  Molecules       Date:  2020-04-02       Impact factor: 4.411

Review 7.  Molecular probes for the human adenosine receptors.

Authors:  Xue Yang; Laura H Heitman; Adriaan P IJzerman; Daan van der Es
Journal:  Purinergic Signal       Date:  2020-12-12       Impact factor: 3.765

8.  Potent PDE4 inhibitor activates AMPK and Sirt1 to induce mitochondrial biogenesis.

Authors:  Sung-Jun Park; Faiyaz Ahmad; Robert J Bahde; Andrew Philp; Jeonghan Kim; Tianjiao Huang; Myung K Kim; William C Trenkle; Jay H Chung
Journal:  PLoS One       Date:  2021-06-17       Impact factor: 3.240
  8 in total

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