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 2010(24): 4193-4198
DOI: 10.1055/s-0030-1258298
DOI: 10.1055/s-0030-1258298
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Microwave-Assisted Synthesis of KN-93, a Potent and Selective Inhibitor of Ca²+/Calmoduline-Dependent Protein Kinase II
Weitere Informationen
Received
1 July 2010
Publikationsdatum:
14. Oktober 2010 (online)
Publikationsverlauf
Publikationsdatum:
14. Oktober 2010 (online)
Abstract
Convenient synthetic routes to KN-93, N-(2-{[[(2E)-3-(4-chlorophenyl)prop-2-enyl](methyl)amino]methyl}phenyl)-N-(2-hydroxyethyl)-4-methoxybenzenesulfonamide, a well-known Ca²+/calmoduline-dependent protein kinase II (CaMKII) inhibitor, are described. The methods proposed start from easily available reagents and allow ready preparation of the final compound in moderate overall yields. Most of the synthetic steps proposed were microwave assisted.
Key words
Heck reaction - sulfonamides - enzymes - multicomponent reaction - medicinal chemistry
- 1
Soderling TR. Trends Biochem. Sci. 1999, 24: 232 - 2
Hook SS.Means AR. Annu. Rev. Pharmacol. Toxicol. 2001, 41: 471 - 3
Soderling TR.Stull JT. Chem. Rev. 2001, 101: 2341 - 4
Hudmon A.Schulman H. Biochem. J. 2002, 364: 593 - 5
Hudmon A.Schulman H. Annu. Rev. Biochem. 2002, 71: 473 - 6
Griffith LC. Cell 2008, 133: 397 - 7
Hanson PI.Schulman H. Annu. Rev. Biochem. 1992, 61: 559 - 8
Braun AP.Schulman H. Annu. Rev. Physiol. 1995, 57: 417 - 9
Soderling TR. Adv. Second Messenger Phosphoprotein Res. 1995, 30: 17 - 10
Schulman H.Braun A. In Calcium as a Cellular RegulatorCrafoli E.Klee C. Oxford University Press; New York: 1999. p.311-343 - 11
Heist EK.Schulman H. Cell Calcium 1998, 23: 103 - 12
Soderling TR.Chang B.Brickey D. J. Biol. Chem. 2001, 276: 3719 - 13
Wang ZJ.Tang L.Xin L. Eur. J. Pharmacol. 2003, 465: 199 - 14
Luo F.Yang C.Chen Y.Shukla P.Tang L.Wang LX.Wang ZJ. J. Pharmacol. Exp. Ther. 2008, 325: 267 - 15
McKinsey TA. Cardiovasc. Res. 2007, 73: 667 - 16
Cai H.Liu D.Garcia JGN. Cardiovasc. Res. 2008, 77: 30 - 17
Sumi M.Kiuchi K.Ishikawa T.Ishii A.Hagiwara M.Nagatsu T.Hidaka H. Biochem. Biophys. Res. Commun. 1991, 181: 968 - 18
Hidaka H,Ishikawa T,Inoe T,Morita T,Nakano H,Yuasa M,Naito K,Sakuma O,Kidokoro S, andTachikawa M. inventors; Jpn. Kokai Tokkyo Koho JP 06293730. ; Chem. Abstr. 1995, 122, 314463 - 19
Bruno C.Carocci A.Catalano A.Cavalluzzi MM.Corbo F.Franchini C.Lentini G.Tortorella V. Chirality 2006, 18: 227 - 20
Boyer JH.Alul H. J. Am. Chem. Soc. 1959, 81: 2136 - 21
Hendrickson JB.Bergeron R. Tetrahedron Lett. 1970, 345 - 22
Bogdal D. In Microwave-Assisted Organic Synthesis Vol. 25:Bäckvall J.-E.Baldwin JE.Williams RM. Elsevier; Oxford: 2005. p.55-56 - 23
Battistuzzi G.Cacchi S.Fabrizi G. Org. Lett. 2003, 5: 777 - 24
Mancuso AJ.Huang S.-L.Swern D. J. Org. Chem. 1978, 43: 2480 - 25
Penjiševic J.Šukalovic V.Andrić D.Kostić-Rajačić S.Šoškic V.Roglić G. Arch. Pharm. Chem. Life Sci. 2007, 340: 456 - 26
Daubresse N.Francesch C.Rolando C. Tetrahedron 1998, 54: 10761 - 27
Still WC.Kahn M.Mitra A. J. Org. Chem. 1978, 43: 2923 - 28
Olsen DK.Torian BE.Morgan CD.Braun LL.
J. Org. Chem. 1980, 45: 4049