8-epi-salvinorin B: Crystal structure and affinity at the κ opioid receptor

Beilstein Journal of Organic Chemistry

Volumn 3, Issue , 2007, Pages

  Munro, Thomas A ^a   Duncan, Katharine K ^a   Staples, Richard J ^b   Xu, Wei ^c   Liu Chen, Lee Yuan ^c   Béguin, Cécile ^a   Carlezon Jr , William A ^a   Cohen, Bruce M ^a  

^a MCLEAN HOSPITAL   (United States)

^b HARVARD UNIVERSITY   (United States)

^c TEMPLE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33847245845     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.1186/1860-5397-3-1     Document Type: Article

References (28)

1. A Ortega JF Blount PS Manchand, J Chem Soc, Perkin Trans 1 1982 2505 2508 doi: 10.1039/P19820002505 10.1039/p19820002505
2. BL Roth K Baner R Westkaemper D Siebert KC Rice S Steinberg P Ernsberger RB Rothman, Proc Natl Acad Sci USA 2002 99 11934 11939 doi: 10.1073/pnas. 182234399 12192085 10.1073/pnas.182234399
3. PM Beardsley JL Howard KL Shelton FI Carroll, Psychopharmacology (Berl) 2005 183 118 26 doi: 10.1007/s00213-005-0167-4 10.1007/s00213-005-0167-4 16184376
4. WA Carlezon Jr C Béguin JA DiNieri MH Baumann MR Richards MS Todtenkopf RB Rothman Z Ma DY Lee BM Cohen, J Pharmacol Exp Ther 2006 316 440 7 doi: 10.1124/jpet.105.092304 10.1124/jpet.105.092304 16223871
5. SD Mague AM Pliakas MS Todtenkopf HC Tomasiewicz Y Zhang WC Stevens Jr RM Jones PS Portoghese WA Carlezon Jr, J Pharmacol Exp Ther 2003 305 323 30 doi: 10.1124/jpet.102.046433 10.1124/jpet.102.046433 12649385
6. MS Todtenkopf JF Marcus PS Portoghese WA Carlezon Jr, Psychopharmacology (Berl) 2004 172 463 70 doi: 10.1007/s00213-003-1680-y 10.1007/s00213-003-1680-y 14727002
7. C Béguin MR Richards Y Wang Y Chen L-Y Liu-Chen Z Ma DYW Lee J Carlezon A William BM Cohen, Bioorg Med Chem Lett 2005 15 2761 2765 doi: 10.1016/j.bmcl.2005.03.113 10.1016/j.bmcl.2005.03.113 15869877
8. DYW Lee VVR Karnati M He L-Y Liu-Chen L Kondareti Z Ma Y Wang Y Chen C Béguin WA Carlezon B Cohen, Bioorg Med Chem Lett 2005 15 3744 3747 doi: 10.1016/j.bmcl.2005.05.048 10.1016/j.bmcl.2005.05.048 15993589
9. WW Harding K Tidgewell N Byrd H Cobb CM Dersch ER Butelman RB Rothman TE Prisinzano, J Med Chem 2005 48 4765 4771 doi: 10.1021/jm048963m 10.1021/jm048963m 16033256
10. J Ma N Ye N Lange BM Cohen, Neuroscience 2003 121 991 8 doi: 10.1016/S0306-4522(03)00397-X 10.1016/S0306-4522(03)00397-X 14580949
11. LJJ Valdés III WM Butler GM Hatfield AG Paul M Koreeda, J Org Chem 1984 49 4716 4720 doi: 10.1021/jo00198a026 10.1021/jo00198a026
12. L Brown, PhD Thesis University of Michigan 1984 http://wwwlib.umi.com/ dissertations/fullcit/8422201
13. M Koreeda L Brown LJJ Valdés III, Chem Lett 1990 2015 2018 doi: 10.1246/cl.1990.2015 10.1246/cl.1990.2015
14. LJJ Valdés III, J Psychoact Drugs 1994 26 277 283
15. LJJ Valdés III HM Chang DC Visger M Koreeda, Org Lett 2001 3 3935 3937 doi: 10.1021/ol016820d 10.1021/ol016820d 11720573
16. TA Munro MA Rizzacasa BL Roth BA Toth F Yan, J Med Chem 2005 48 345 348 doi: 10.1021/jm049438q 10.1021/jm049438q 15658846
17. TA Munro, PhD Thesis University of Melbourne 2006 http://eprints.infodiv. unimelb.edu.au/archive/00002327
18. WW Harding M Schmidt K Tidgewell P Kannan KG Holden CM Dersch RB Rothman TE Prisinzano, Bioorg Med Chem Lett 2006 16 3170 3174 doi: 10.1016/j.bmcl.2006. 03.062 10.1016/j.bmcl.2006.03.062 16621556
19. TA Munro GW Goetchius BL Roth TA Vortherms MA Rizzacasa, J Org Chem 2005 70 10057 10061 doi: 10.1021/jo051813e 10.1021/jo051813e 16292839
20. C Béguin MR Richards J-G Li Y Wang W Xu L-Y Liu-Chen WA Carlezon BM Cohen, Bioorg Med Chem Lett 2006 16 4679 4685 doi: 10.1016/j.bmcl.2006.05.093 10.1016/j.bmcl.2006.05.093 16777411
21. C Béguin W Carlezon BM Cohen M He DY-W Lee MR Richards L-Y Liu-Chen, Salvinorin derivatives and uses thereof. US Patent Application 20060052439 2006
22. WW Harding M Schmidt K Tidgewell P Kannan KG Holden B Gilmour H Navarro RB Rothman TE Prisinzano, J Nat Prod 2006 69 107 112 doi: 10.1021/np050398i 10.1021/np050398i 16441078
23. DY Lee M He L Kondaveti LY Liu-Chen Z Ma Y Wang Y Chen JG Li C Béguin WA Carlezon Jr B Cohen, Bioorg Med Chem Lett 2005 15 4169 4173 doi: 10.1016/j.bmcl.2005.06.092 10.1016/j.bmcl.2005.06.092 16051487
24. DY Lee M He LY Liu-Chen Y Wang JG Li W Xu Z Ma WA Carlezon Jr B Cohen, Bioorg Med Chem Lett 2006 16 5498 5502 doi: 10.1016/j.bmcl.2006.08.051 10.1016/j.bmcl.2006.08.051 16945525
25. CCDC CIF Depository Request Form. http://www.ccdc.cam.ac.uk/data_request/ cif
26. Y Wang K Tang S Inan DJ Siebert U Holzgrabe DYW Lee P Huang J-G Li A Cowan L-Y Liu-Chen, J Pharmacol Exp Ther 2005 312 220 230 doi: 10.1124/jpet.104.073668 10.1124/jpet.104.073668 15383632
27. DYW Lee Z Ma L-Y Liu-Chen Y Wang Y Chen J Carlezon A William B Cohen, Bioorg Med Chem 2005 13 5635 5639 doi: 10.1016/j.bmc.2005.05.054 10.1016/j.bmc.2005.05.054 16084728
28. C Chavkin S Sud W Jin J Stewart JK Zjawiony DJ Siebert BA Toth SJ Hufeisen BL Roth, J Pharmacol Exp Ther 2004 308 1197 1203 doi: 10.1124/jpet.103.059394 10.1124/jpet.103.059394 14718611