Gast ::
| Hauptseite > Publikationsdatenbank > Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands > print |
| Hauptseite > Publikationsdatenbank > Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands > print |
| 001 | 891313 | ||
| 005 | 20230217124544.0 | ||
| 024 | 7 | _ | |a 10.1016/j.ejmech.2021.113214 |2 doi |
| 024 | 7 | _ | |a 0009-4374 |2 ISSN |
| 024 | 7 | _ | |a 0223-5234 |2 ISSN |
| 024 | 7 | _ | |a 1768-3254 |2 ISSN |
| 024 | 7 | _ | |a 2128/27464 |2 Handle |
| 024 | 7 | _ | |a 33548636 |2 pmid |
| 024 | 7 | _ | |a WOS:000629633800015 |2 WOS |
| 037 | _ | _ | |a FZJ-2021-01420 |
| 041 | _ | _ | |a English |
| 082 | _ | _ | |a 610 |
| 100 | 1 | _ | |a Renk, Dana R. |0 P:(DE-Juel1)174096 |b 0 |
| 245 | _ | _ | |a Design, synthesis and biological evaluation of Tozadenant analogues as adenosine A2A receptor ligands |
| 260 | _ | _ | |a Amsterdam [u.a.] |c 2021 |b Elsevier71544 |
| 264 | _ | 1 | |3 print |2 Crossref |b Elsevier BV |c 2021-03-01 |
| 336 | 7 | _ | |a article |2 DRIVER |
| 336 | 7 | _ | |a Output Types/Journal article |2 DataCite |
| 336 | 7 | _ | |a Journal Article |b journal |m journal |0 PUB:(DE-HGF)16 |s 1654069056_6248 |2 PUB:(DE-HGF) |
| 336 | 7 | _ | |a ARTICLE |2 BibTeX |
| 336 | 7 | _ | |a JOURNAL_ARTICLE |2 ORCID |
| 336 | 7 | _ | |a Journal Article |0 0 |2 EndNote |
| 520 | _ | _ | |a 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. |
| 536 | _ | _ | |a 525 - Decoding Brain Organization and Dysfunction (POF4-525) |0 G:(DE-HGF)POF4-525 |c POF4-525 |f POF IV |x 0 |
| 542 | _ | _ | |i 2021-03-01 |2 Crossref |u https://www.elsevier.com/tdm/userlicense/1.0/ |
| 542 | _ | _ | |i 2021-03-01 |2 Crossref |u https://doi.org/10.15223/policy-017 |
| 542 | _ | _ | |i 2021-03-01 |2 Crossref |u https://doi.org/10.15223/policy-037 |
| 542 | _ | _ | |i 2021-03-01 |2 Crossref |u https://doi.org/10.15223/policy-012 |
| 542 | _ | _ | |i 2021-03-01 |2 Crossref |u https://doi.org/10.15223/policy-029 |
| 542 | _ | _ | |i 2021-03-01 |2 Crossref |u https://doi.org/10.15223/policy-004 |
| 588 | _ | _ | |a Dataset connected to CrossRef |
| 700 | 1 | _ | |a Skraban, Marcel |0 P:(DE-Juel1)157984 |b 1 |
| 700 | 1 | _ | |a Bier, Dirk |0 P:(DE-Juel1)131810 |b 2 |u fzj |
| 700 | 1 | _ | |a Schulze, Annette |0 P:(DE-Juel1)131847 |b 3 |u fzj |
| 700 | 1 | _ | |a Wabbals, Erika |0 P:(DE-Juel1)131852 |b 4 |
| 700 | 1 | _ | |a Wedekind, Franziska |0 P:(DE-Juel1)131711 |b 5 |u fzj |
| 700 | 1 | _ | |a Neumaier, Felix |0 P:(DE-Juel1)175142 |b 6 |
| 700 | 1 | _ | |a Neumaier, Bernd |0 P:(DE-Juel1)166419 |b 7 |u fzj |
| 700 | 1 | _ | |a Holschbach, Marcus |0 P:(DE-Juel1)131824 |b 8 |e Corresponding author |
| 773 | 1 | 8 | |a 10.1016/j.ejmech.2021.113214 |b Elsevier BV |d 2021-03-01 |p 113214 |3 journal-article |2 Crossref |t European Journal of Medicinal Chemistry |v 214 |y 2021 |x 0223-5234 |
| 773 | _ | _ | |a 10.1016/j.ejmech.2021.113214 |g Vol. 214, p. 113214 - |0 PERI:(DE-600)2005170-0 |p 113214 |t European journal of medicinal chemistry |v 214 |y 2021 |x 0223-5234 |
| 856 | 4 | _ | |u https://juser.fz-juelich.de/record/891313/files/1-s2.0-S0223523421000635-main.pdf |y Restricted |
| 856 | 4 | _ | |u https://juser.fz-juelich.de/record/891313/files/EJMECH-D-20-03196_For_Central_Library.pdf |y Published on 2020-01-30. Available in OpenAccess from 2022-01-30. |
| 909 | C | O | |o oai:juser.fz-juelich.de:891313 |p openaire |p open_access |p VDB |p driver |p dnbdelivery |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 0 |6 P:(DE-Juel1)174096 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 2 |6 P:(DE-Juel1)131810 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 3 |6 P:(DE-Juel1)131847 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 4 |6 P:(DE-Juel1)131852 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 5 |6 P:(DE-Juel1)131711 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 6 |6 P:(DE-Juel1)175142 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 7 |6 P:(DE-Juel1)166419 |
| 910 | 1 | _ | |a Forschungszentrum Jülich |0 I:(DE-588b)5008462-8 |k FZJ |b 8 |6 P:(DE-Juel1)131824 |
| 913 | 1 | _ | |a DE-HGF |b Key Technologies |l Natural, Artificial and Cognitive Information Processing |1 G:(DE-HGF)POF4-520 |0 G:(DE-HGF)POF4-525 |3 G:(DE-HGF)POF4 |2 G:(DE-HGF)POF4-500 |4 G:(DE-HGF)POF |v Decoding Brain Organization and Dysfunction |x 0 |
| 913 | 0 | _ | |a DE-HGF |b Key Technologies |l Decoding the Human Brain |1 G:(DE-HGF)POF3-570 |0 G:(DE-HGF)POF3-573 |3 G:(DE-HGF)POF3 |2 G:(DE-HGF)POF3-500 |4 G:(DE-HGF)POF |v Neuroimaging |x 0 |
| 914 | 1 | _ | |y 2021 |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0200 |2 StatID |b SCOPUS |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)1030 |2 StatID |b Current Contents - Life Sciences |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0600 |2 StatID |b Ebsco Academic Search |
| 915 | _ | _ | |a Creative Commons Attribution-NonCommercial-NoDerivs CC BY-NC-ND 4.0 |0 LIC:(DE-HGF)CCBYNCND4 |2 HGFVOC |
| 915 | _ | _ | |a Embargoed OpenAccess |0 StatID:(DE-HGF)0530 |2 StatID |
| 915 | _ | _ | |a JCR |0 StatID:(DE-HGF)0100 |2 StatID |b EUR J MED CHEM : 2015 |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0150 |2 StatID |b Web of Science Core Collection |
| 915 | _ | _ | |a WoS |0 StatID:(DE-HGF)0110 |2 StatID |b Science Citation Index |
| 915 | _ | _ | |a WoS |0 StatID:(DE-HGF)0111 |2 StatID |b Science Citation Index Expanded |
| 915 | _ | _ | |a IF < 5 |0 StatID:(DE-HGF)9900 |2 StatID |
| 915 | _ | _ | |a Peer Review |0 StatID:(DE-HGF)0030 |2 StatID |b ASC |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0310 |2 StatID |b NCBI Molecular Biology Database |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)1050 |2 StatID |b BIOSIS Previews |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0300 |2 StatID |b Medline |
| 915 | _ | _ | |a DBCoverage |0 StatID:(DE-HGF)0199 |2 StatID |b Thomson Reuters Master Journal List |
| 920 | 1 | _ | |0 I:(DE-Juel1)INM-5-20090406 |k INM-5 |l Nuklearchemie |x 0 |
| 920 | 1 | _ | |0 I:(DE-Juel1)INM-2-20090406 |k INM-2 |l Molekulare Organisation des Gehirns |x 1 |
| 980 | _ | _ | |a journal |
| 980 | _ | _ | |a VDB |
| 980 | _ | _ | |a I:(DE-Juel1)INM-5-20090406 |
| 980 | _ | _ | |a I:(DE-Juel1)INM-2-20090406 |
| 980 | _ | _ | |a UNRESTRICTED |
| 980 | 1 | _ | |a FullTexts |
| 999 | C | 5 | |1 Fredholm |y 2001 |2 Crossref |o Fredholm 2001 |
| 999 | C | 5 | |a 10.1523/JNEUROSCI.5066-06.2007 |9 -- missing cx lookup -- |1 Elmenhorst |p 2410 - |2 Crossref |t J. Neurosci. |v 27 |y 2007 |
| 999 | C | 5 | |a 10.3109/07853899908998788 |9 -- missing cx lookup -- |1 Porkka-Heiskanen |p 125 - |2 Crossref |t Ann. Med. |v 31 |y 1999 |
| 999 | C | 5 | |a 10.1016/S0306-4522(96)00640-9 |9 -- missing cx lookup -- |1 Portas |p 225 - |2 Crossref |t Neuroscience |v 79 |y 1997 |
| 999 | C | 5 | |a 10.1016/B978-0-12-801022-8.00012-X |p 257 - |1 Chen |y 2014 |2 Crossref |9 -- missing cx lookup -- |
| 999 | C | 5 | |a 10.2741/2870 |9 -- missing cx lookup -- |1 Takahashi |p 2614 - |2 Crossref |t Front. Biosci. |v 13 |y 2008 |
| 999 | C | 5 | |a 10.1016/0033-0620(81)90030-X |9 -- missing cx lookup -- |1 Berne |p 243 - |2 Crossref |t Prog. Cardiovasc. Dis. |v 24 |y 1981 |
| 999 | C | 5 | |1 Dirnagl |y 1994 |2 Crossref |o Dirnagl 1994 |
| 999 | C | 5 | |a 10.1016/B978-0-12-801022-8.00003-9 |p 71 - |1 Jenner |y 2014 |2 Crossref |9 -- missing cx lookup -- |
| 999 | C | 5 | |a 10.1111/j.1460-9568.2009.06897.x |9 -- missing cx lookup -- |1 D’Alimonte |p 1023 - |2 Crossref |t Eur. J. Neurosci. |v 30 |y 2009 |
| 999 | C | 5 | |a 10.1016/j.jpsychires.2013.12.013 |9 -- missing cx lookup -- |1 Villar-Menéndez |p 49 - |2 Crossref |t J. Psychiatr. Res. |v 51 |y 2014 |
| 999 | C | 5 | |a 10.1038/sj.bjp.0704240 |9 -- missing cx lookup -- |1 El Yacoubi |p 68 - |2 Crossref |t Br. J. Pharmacol. |v 134 |y 2001 |
| 999 | C | 5 | |a 10.1155/2017/6975841 |9 -- missing cx lookup -- |1 Vuorimaa |p 1 - |2 Crossref |t Contrast Media Mol. Imaging |y 2017 |
| 999 | C | 5 | |a 10.1002/med.21432 |9 -- missing cx lookup -- |1 van Waarde |p 5 - |2 Crossref |t Med. Res. Rev. |v 38 |y 2018 |
| 999 | C | 5 | |a 10.1016/0306-4522(91)90038-P |9 -- missing cx lookup -- |1 Martinez-Mir |p 697 - |2 Crossref |t Neuroscience |v 42 |y 1991 |
| 999 | C | 5 | |a 10.1385/JMN:26:2-3:209 |9 -- missing cx lookup -- |1 Fuxe |p 209 - |2 Crossref |t J. Mol. Neurosci. |v 26 |y 2005 |
| 999 | C | 5 | |a 10.2967/jnumed.114.152546 |9 -- missing cx lookup -- |1 Barret |p 586 - |2 Crossref |t J. Nucl. Med. |v 56 |y 2015 |
| 999 | C | 5 | |a 10.1016/S1474-4422(11)70012-6 |9 -- missing cx lookup -- |1 Hauser |p 221 - |2 Crossref |t Lancet Neurol. |v 10 |y 2011 |
| 999 | C | 5 | |a 10.1007/s40265-013-0066-7 |9 -- missing cx lookup -- |1 Dungo |p 875 - |2 Crossref |t Drugs |v 73 |y 2013 |
| 999 | C | 5 | |a 10.3390/ph13090237 |9 -- missing cx lookup -- |1 Zhang |p 237 - |2 Crossref |t Pharmaceuticals |v 13 |y 2020 |
| 999 | C | 5 | |a 10.1021/acs.jmedchem.0c00237 |9 -- missing cx lookup -- |1 Yu |p 12196 - |2 Crossref |t J. Med. Chem. |v 63 |y 2020 |
| 999 | C | 5 | |a 10.1021/jm4011669 |9 -- missing cx lookup -- |1 de Lera Ruiz |p 3623 - |2 Crossref |t J. Med. Chem. |v 57 |y 2014 |
| 999 | C | 5 | |1 Shah |y 2010 |2 Crossref |o Shah 2010 |
| 999 | C | 5 | |a 10.1021/jm9911480 |9 -- missing cx lookup -- |1 Sauer |p 440 - |2 Crossref |t J. Med. Chem. |v 43 |y 2000 |
| 999 | C | 5 | |a 10.1212/01.WNL.0000095219.22086.31 |9 -- missing cx lookup -- |1 Kase |p 97 - |2 Crossref |t Neurology |v 61 |y 2003 |
| 999 | C | 5 | |1 Williams |y 1987 |2 Crossref |o Williams 1987 |
| 999 | C | 5 | |a 10.1016/S0960-894X(01)80279-1 |9 -- missing cx lookup -- |1 Baraldi |p 2539 - |2 Crossref |t Med. Chem. Lett. |v 4 |y 1994 |
| 999 | C | 5 | |a 10.1039/p19950000801 |9 -- missing cx lookup -- |1 Caulkett |p 801 - |2 Crossref |t J. Chem. Soc., Perkin Trans. |v 1 |y 1995 |
| 999 | C | 5 | |1 Vu |y 2005 |2 Crossref |o Vu 2005 |
| 999 | C | 5 | |2 Crossref |u A. Flohr, J.-L. Moreau, S.M. Poli, C. Riemer, L. Steward, 4-Hydroxy-4-methyl-piperidine-1-carboxylic Acid (4-Methoxy-7-Morpholin-4-Yl-Benzothiazol-2-Yl)-Amide, US Patent US 7368446 B2 (2008).. |
| 999 | C | 5 | |1 Yuan |y 2017 |2 Crossref |o Yuan 2017 |
| 999 | C | 5 | |a 10.1021/acs.jmedchem.6b01584 |9 -- missing cx lookup -- |1 Basu |p 681 - |2 Crossref |t J. Med. Chem. |v 60 |y 2017 |
| 999 | C | 5 | |a 10.1021/jm9705465 |9 -- missing cx lookup -- |1 Holschbach |p 555 - |2 Crossref |t J. Med. Chem. |v 41 |y 1998 |
| 999 | C | 5 | |a 10.1021/op700074k |9 -- missing cx lookup -- |1 Zhang |p 861 - |2 Crossref |t Org. Process Res. Dev. |v 11 |y 2007 |
| 999 | C | 5 | |2 Crossref |u P. Spurr, Cyclization Process for Substituted Benzothiazol Derivatives, US Patent US 7081761 B2 (2006).. |
| 999 | C | 5 | |a 10.1021/jacs.5b06307 |9 -- missing cx lookup -- |1 Nielsen |p 9571 - |2 Crossref |t J. Am. Chem. Soc. |v 137 |y 2015 |
| 999 | C | 5 | |a 10.1021/jacs.7b07891 |9 -- missing cx lookup -- |1 Parisi |p 13648 - |2 Crossref |t J. Am. Chem. Soc. |v 139 |y 2017 |
| 999 | C | 5 | |a 10.1021/ja00713a071 |9 -- missing cx lookup -- |1 Rathke |p 3222 - |2 Crossref |t J. Am. Chem. Soc. |v 92 |y 1970 |
| 999 | C | 5 | |a 10.1055/s-1997-1335 |9 -- missing cx lookup -- |1 Thavonekham |p 1189 - |2 Crossref |t Synthesis |v 1997 |y 1997 |
| 999 | C | 5 | |a 10.1021/ja01084a034 |9 -- missing cx lookup -- |1 Corey |p 1353 - |2 Crossref |t J. Am. Chem. Soc. |v 87 |y 1965 |
| 999 | C | 5 | |a 10.1021/ja00230a045 |9 -- missing cx lookup -- |1 Gao |p 7538 - |2 Crossref |t J. Am. Chem. Soc. |v 110 |y 1968 |
| 999 | C | 5 | |1 Armarego |y 2009 |2 Crossref |o Armarego 2009 |
| 999 | C | 5 | |2 Crossref |u E. Verner, K.A. Brameld, Quinolone Derivatives as Fibroblast Growth Factor Receptor Inhibitors, US Patent WO 2015120049 A1 (2015).. |
| 999 | C | 5 | |2 Crossref |u J.J. Crawford, J. Drobnick, L.J. Zard, W. Lee, C. Ndubaku, J. Rudolph, Pyrimidine-pyridinone Serine/threonine Kinase Inhibitors, US Patent WO 2015011252 A1 (2015).. |
| 999 | C | 5 | |a 10.1021/ja9806128 |9 -- missing cx lookup -- |1 Evans |p 5921 - |2 Crossref |t J. Am. Chem. Soc. |v 120 |y 1998 |
| 999 | C | 5 | |a 10.1016/S0040-4039(01)80274-4 |9 -- missing cx lookup -- |1 Kim |p 655 - |2 Crossref |t Tetrahedron Lett. |v 30 |y 1989 |
| 999 | C | 5 | |a 10.1111/j.1471-4159.2006.03666.x |9 -- missing cx lookup -- |1 Wachten |p 1580 - |2 Crossref |t J. Neurochem. |v 96 |y 2006 |
| 999 | C | 5 | |1 Chen |y 1987 |2 Crossref |o Chen 1987 |
| 999 | C | 5 | |a 10.1007/BF00518781 |9 -- missing cx lookup -- |1 Lohse |p 69 - |2 Crossref |t Naunyn-Schmiedeberg’s Arch. Pharmacol. |v 326 |y 1984 |
| 999 | C | 5 | |a 10.1515/bchm2.1979.360.2.1657 |9 -- missing cx lookup -- |1 Neuhoff |p 1657 - |2 Crossref |t Z. Physiol. Chem. |v 360 |y 1979 |
| 999 | C | 5 | |a 10.1089/adt.2020.991 |9 -- missing cx lookup -- |1 Bier |p 328 - |2 Crossref |t Assay Drug Dev. Technol. |v 18 |y 2020 |
| Library | Collection | CLSMajor | CLSMinor | Language | Author |
|---|