Modification of the furan ring of salvinorin A: Identification of a selective partial agonist at the kappa opioid receptor

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 3, 2009, Pages 1370-1380

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

^a MCLEAN HOSPITAL   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

^c HARVARD UNIVERSITY   (United States)

^d TEMPLE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

35S GTP S; Binding; Kappa opioid receptor agonists; Salvinorin

Indexed keywords

12 EPI SALVINORIN A; CARBON; FURAN; KAPPA OPIATE RECEPTOR AGONIST; SALVINORIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

DITERPENES, CLERODANE; FURANS; RECEPTORS, OPIOID, KAPPA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 58949093385     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.12.012     Document Type: Article

References (32)

1. Shippenberg T.S., Zapata A., and Chefer V.I. Pharmacol. Ther. 116 (2007) 306
2. Mague S.D., Pliakas A.M., Todtenkopf M.S., Tomasiewicz H.C., Zhang Y., Stevens Jr. W.C., Jones R.M., Portoghese P.S., and Carlezon Jr. W.A. J. Pharmacol. Exp. Ther. 305 (2003) 323
3. Nestler E.J., and Carlezon Jr. W.A. Biol. Psychiatry 59 (2006) 1151
4. Knoll A.T., Meloni E.G., Thomas J.B., Carroll F.I., and Carlezon Jr. W.A. J. Pharmacol. Exp. Ther. 323 (2007) 838
5. Portoghese P.S., Lipkowski A.W., and Takemori A.E. Life Sci. 40 (1987) 1287
6. Broadbear J.H., Negus S.S., Butelman E.R., de Costa B.R., and Woods J.H. Psychopharmacology (Berlin Ger.) 115 (1994) 311
7. Negus S.S., Mello N.K., Linsenmayer D.C., Jones R.M., and Portoghese P.S. Psychopharmacology (Berlin Ger.) 163 (2002) 412
8. Jones R.M., and Portoghese P.S. Eur. J. Pharmacol. 396 (2000) 49
9. Stevens Jr. W.C., Jones R.M., Subramanian G., Metzger T.G., Ferguson D.M., and Portoghese P.S. J. Med. Chem. 43 (2000) 2759
10. Thomas J.B., Atkinson R.N., Rothman R.B., Fix S.E., Mascarella S.W., Vinson N.A., Xu H., Dersch C.M., Lu Y., Cantrell B.E., Zimmerman D.M., and Carroll F.I. J. Med. Chem. 44 (2001) 2687
11. Carroll I., Thomas J.B., Dykstra L.A., Granger A.L., Allen R.M., Howard J.L., Pollard G.T., Aceto M.D., and Harris L.S. Eur. J. Pharmacol. 501 (2004) 111
12. Ortega A., Blount J.F., and Manchand P.S. J. Chem. Soc., Perkin Trans. 1 (1982) 2505
13. Roth B.L., Baner K., Westkaemper R., Siebert D., Rice K.C., Steinberg S., Ernsberger P., and Rothman R.B. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 11934
14. Prisinzano T.E., and Rothman R.B. Chem. Rev. (Washington, DC, US) 108 (2008) 1732
15. Butelman E.R., Harris T.J., and Kreek M.J. Psychopharmacology (Berlin, Ger.) 172 (2004) 220
16. McCurdy C.R., Sufka K.J., Smith G.H., Warnick J.E., and Nieto M.J. Pharmacol. Biochem. Behav. 83 (2006) 109
17. Beguin C., Potter D.N., Dinieri J.A., Munro T.A., Richards M.R., Paine T.A., Berry L., Zhao Z., Roth B.L., Xu W., Liu-Chen L.Y., Carlezon Jr. W.A., and Cohen B.M. J. Pharmacol. Exp. Ther. 324 (2008) 188
18. Beguin C., Richards M.R., Wang Y., Chen Y., Liu-Chen L.Y., Ma Z., Lee D.Y., Carlezon Jr. W.A., and Cohen B.M. Bioorg. Med. Chem. Lett. 15 (2005) 2761
19. Beguin C., Richards M.R., Li J.G., Wang Y., Xu W., Liu-Chen L.Y., Carlezon Jr. W.A., and Cohen B.M. Bioorg. Med. Chem. Lett. 16 (2006) 4679
20. Simpson D.S., Katavic P.L., Lozama A., Harding W.W., Parrish D., Deschamps J.R., Dersch C.M., Partilla J.S., Rothman R.B., Navarro H., and Prisinzano T.E. J. Med. Chem. 50 (2007) 3596
21. Munro T.A., Rizzacasa M.A., Roth B.L., Toth B.A., and Yan F. J. Med. Chem. 48 (2005) 345
22. Harding W.W., Schmidt M., Tidgewell K., Kannan P., Holden K.G., Gilmour B., Navarro H., Rothman R.B., and Prisinzano T.E. J. Nat. Prod. 69 (2006) 107
23. Harding W.W., Schmidt M., Tidgewell K., Kannan P., Holden K.G., Dersch C.M., Rothman R.B., and Prisinzano T.E. Bioorg. Med. Chem. Lett. 16 (2006) 3170
24. John K.S. Angew. Chem., Int. Ed. 25 (1986) 508
25. Bikbulatov R.V., Stewart J., Jin W., Yan F., Roth B.L., Ferreira D., and Zjawiony J.K. Tetrahedron Lett. 49 (2008) 937
26. Overton K.H., Weir N.G., and Wylie A. J. Chem. Soc. C (1966) 1482
27. Koreeda M., Brown L., and Valdes III L.J. Chem. Lett. 19 (1990) 2015
28. Munro T.A., Duncan K.K., Staples R.J., Xu W., Liu-Chen L.Y., Beguin C., Carlezon Jr. W.A., and Cohen B.M. Beilstein J. Org. Chem. 3 (2007) 1
29. Wang Y., Tang K., Inan S., Siebert D., Holzgrabe U., Lee D.Y., Huang P., Li J.G., Cowan A., and Liu-Chen L.Y. J. Pharmacol. Exp. Ther. 312 (2005) 220
30. Zhu J., Luo L.Y., Li J.G., Chen C., and Liu-Chen L.Y. J. Pharmacol. Exp. Ther. 282 (1997) 676
31. Scheerer J.R., Lawrence J.F., Wang G.C., and Evans D.A. J. Am. Chem. Soc. 129 (2007) 8968
32. Nozawa M., Suka Y., Hoshi T., Suzuki T., and Hagiwara H. Org. Lett. 10 (2008) 1365