RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2011(17): 2733-2736
DOI: 10.1055/s-0030-1260103
DOI: 10.1055/s-0030-1260103
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 1,2,3-Triazole Elements in Histamine H3 Receptor Ligands
Weitere Informationen
Received
25 February 2011
Publikationsdatum:
08. Juli 2011 (online)
Publikationsverlauf
Publikationsdatum:
08. Juli 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201117/lookinside/thumbnails/10.1055-s-0030-1260103-1.jpg)
Abstract
1,2,3-Triazole moieties were introduced in a histamine H3 receptor antagonist pharmacophore blueprint with a versatile click chemistry approach, yielding potent ligands. Azide and alkynes were combined under copper(I) catalysis to provide the triazole element. Conventional synthesis, as well as microwave irradiation, was successfully applied.
Key words
azides - alkynes - copper catalysis - click chemistry - histamine H3 receptor
-
1a
Leurs R.Bakker RA.Timmerman H.de Esch IJ. Nat. Rev. Drug Discovery 2005, 4: 1070 -
1b
Tiligada E.Zampeli E.Sander K.Stark H. Expert Opin. Invest. Drugs 2009, 18: 1519 -
2a
Raddatz R.Tao M.Hudkins RL. Curr. Top. Med. Chem. 2010, 10: 153 -
2b
Brioni JD.Esbenshade TA.Garrison TR.Bitner SR.Cowart MD. J. Pharmacol. Exp. Ther. 2011, 336: 38 -
2c
Walter M.Stark H. Front. Biosci. 2011, in press -
3a
Celanire S.Wijtmans M.Talaga P.Leurs R.de Esch IJ. Drug Discovery Today 2005, 10: 1613 -
3b
Celanire S.Lebon F.Stark H. In The Third Histamine Receptor: Selective Ligands as Potential Therapeutic Agents in CNS DisordersVohora DS. Taylor & Francis, CRC Press Inc.; Boca Raton: 2008. p.103 -
3c
Sander K.von Coburg Y.Camelin JC.Ligneau X.Rau O.Schubert-Zsilavecz M.Schwartz JC.Stark H. Bioorg. Med. Chem. Lett. 2010, 20: 1581 -
4a
Denonne F.Atienzar F.Celanire S.Christophe B.Delannois F.Delaunoy C.Delporte ML.Durieu V.Gillard M.Lallemand B.Lamberty Y.Lorent G.Vanbellinghen A.Van Houtvin N.Verbois V.Provins L. ChemMedChem 2010, 5: 206 -
4b
Davenport AJ.Stimson CC.Corsi M.Vaidya D.Glenn E.Jones TD.Bailey S.Gemkow MJ.Fritz U.Hallett DJ. Bioorg. Med. Chem. Lett. 2010, 20: 5165 -
4c
Rao AU.Palani A.Chen X.Huang Y.Aslanian RG.West RE.Williams SM.Wu RL.Hwa J.Sondey C.Lachowicz J. Bioorg. Med. Chem. Lett. 2009, 19: 6176 -
4d
Swanson DM.Shah CR.Lord B.Morton K.Dvorak LK.Mazur C.Apodaca R.Xiao W.Boggs JD.Feinstein M.Wilson SJ.Barbier AJ.Bonaventure P.Lovenberg TW.Carruthers NI. Eur. J. Med. Chem. 2009, 44: 4413 -
4e
Celanire S.Wijtmans M.Christophe B.Collart P.de Esch I.Dassesse D.Delaunoy C.Denonne F.Durieu V.Gelens E.Gillard M.Lallemand B.Lamberty Y.Lebon F.Nicolas JM.Quere L.Snip E.Vanbellinghen A.Van Houtvin N.Verbois V.Timmerman H.Talaga P.Leurs R.Provins L. ChemMedChem 2009, 4: 1063 -
4f
Walter M.von Coburg Y.Isensee K.Sander K.Ligneau X.Camelin JC.Schwartz JC.Stark H. Bioorg. Med. Chem. Lett. 2010, 20: 5879 -
4g
Walter M.Isensee K.Kottke T.Ligneau X.Camelin JC.Schwartz JC.Stark H. Bioorg. Med. Chem. Lett. 2010, 20: 5883 - 5
Huisgen R. In 1,3-Dipolar Cycloaddition Chemistry Vol. 1:Padwa A. Wiley; New York: 1984. p.1 - 6
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 - 7
Kolb HC.Sharpless KB. Drug Discovery Today 2003, 8: 1128 - 8
Sander K.Kottke T.Hoffend C.Walter M.Weizel L.Camelin JC.Ligneau X.Schneider EH.Seifert R.Schwartz JC.Stark H. Org. Lett. 2010, 12: 2578 -
9a
Ligneau X.Morisset S.Tardivel-Lacombe J.Gbahou F.Ganellin CR.Stark H.Schunack W.Schwartz JC.Arrang JM. Br. J. Pharmacol. 2000, 131: 1247 -
9b
Ligneau X.Perrin D.Landais L.Camelin JC.Calmels TP.Berrebi-Bertrand I.Lecomte JM.Parmentier R.Anaclet C.Lin JS.Bertaina-Anglade V.la Rochelle CD.d’Aniello F.Rouleau A.Gbahou F.Arrang JM.Ganellin CR.Stark H.Schunack W.Schwartz JC. J. Pharmacol. Exp. Ther. 2007, 320: 365 - 10
Kottke T.Sander K.Weizel L.Schneider EH.Seifert R.Stark H. Eur. J. Pharmacol. 2011, 654: 200 - 11
Rodionov VO.Fokin VV.Finn MG. Angew. Chem. Int. Ed. 2005, 44: 2210 -
12a
Amon M.Ligneau X.Schwartz JC.Stark H. Bioorg. Med. Chem. Lett. 2006, 16: 1938 -
12b
Ju Y.Kumar D.Varma RS. J. Org. Chem. 2006, 71: 6697 -
12c
Isensee K.Amon M.Galaparti A.Ligneau X.Camelin JC.Capet M.Schwartz JC.Stark H. Bioorg. Med. Chem. Lett. 2009, 19: 2172 - 13
Appukkuttan P.Dehaen W.Fokin VV.Van der Eycken E. Org. Lett. 2004, 6: 4223 - 14
Hansen SG.Jensen HH. Synlett 2009, 3275