Synthesis and biological evaluation of C-2 halogenated analogs of salvinorin A

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 19, 2010, Pages 5749-5752

  Lee, David Y W ^a   Yang, Lu ^a   Xu, Wei ^b   Deng, Gang ^a   Guo, Lin ^a   Liu Chen, Lee Yuan ^b  

^a MCLEAN HOSPITAL   (United States)

^b TEMPLE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Halogenation; Kappa; Salvinorin A

Indexed keywords

3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE METHANESULFONATE; BROMINE; CARBON; DELTA OPIATE RECEPTOR; ETORPHINE; FLUORINE; HALOGEN; IODINE; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; SALVINORIN A; TERPENOID;

ARTICLE; ATOM; BINDING AFFINITY; DRUG SYNTHESIS; ELECTRON; HALOGENATION; IODINATION; ISOMER; LIPOPHILICITY; MOLECULAR PROBE; NEUROIMAGING; PLANT; POSITRON EMISSION TOMOGRAPHY; RECEPTOR BINDING; SALVIA DIVINORUM; SCREENING; STRUCTURE ACTIVITY RELATION;

DITERPENES, CLERODANE; HALOGENATION; ISOMERISM; KINETICS; POSITRON-EMISSION TOMOGRAPHY; PROTEIN BINDING; RECEPTORS, OPIOID, KAPPA; SALVIA; STRUCTURE-ACTIVITY RELATIONSHIP;

SALVIA DIVINORUM;

EID: 77957605908     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.001     Document Type: Article

References (24)

1. D.J. Siebert J. Ethnopharmacol. 43 1994 53
2. E.R. Butelman, T.E. Prisinzano, H. Deng, S. Rus, and M.J. Kreek J. Pharmacol. Exp. Ther. 328 2009 588
3. W.W. Harding, K. Tidgewell, M. Schmidt, K. Shah, C.M. Dersch, J. Snyder, D. Parrish, J.R. Deschamps, R.B. Rothman, and T.E. Prisinzano Org. Lett. 7 2005 3017
4. D. González, J. Riba, J.C. Bouso, G. Gómez-Jarabo, and M.J. Barbanoj Drug Alcohol Depend. 85 2006 157
5. A. Ortega, J.F. Blount, and P.S. Manchand J. Chem. Soc., Perkin Trans. 1 1982 2505
6. L.J. Valdes III, W.M. Butler, G.M. Hatfield, A.G. Paul, and M. Koreeda J. Org. Chem. 49 1984 4716
7. B.L. Roth, K. Baner, R. Westkaemper, D.J. Siebert, K.C. Rice, S. Steinberg, P. Ernsberger, and R.B. Rothman Proc. Natl. Acad. Sci. U.S.A. 99 2002 11934
8. D.J. Sheffler, and B.L. Roth Trends Pharmacol. Sci. 24 2003 107
9. B.L. Roth, K. Baner, R. Westkaemper, D. Siebert, K.C. Rice, S. Steinberg, P. Ernsberger, and R.B. Rothman Proc. Natl. Acad. Sci. U.S.A. 99 2002 11934
10. T.E. Prisinzano, and R.B. Rothman Chem. Rev. 108 2008 1732
11. D.Y.W. Lee, V.V.R. Karnati, M. He, L.Y. Liu-Chen, L. Kondareti, Z. Ma, Y. Wang, Y. Chen, C. Beguin, W.A. Carlezon, and B. Cohen Bioorg. Med. Chem. Lett. 15 2005 3744
12. T.A. Munro, K.K. Duncan, W. Xu, Y. Wang, L.Y. Liu-Chen, W.A. Carlezon, B.M. Cohen, and C. Beguin Bioorg. Med. Chem. 16 2008 1279
13. Y. Wang, Y. Chen, W. Xu, D.Y.W. Lee, Z. Ma, S.M. Rawls, A. Cowan, and L.Y. Liu-Chen J. Pharmacol. Exp. Ther. 324 2008 1073
14. Y. Lu, T. Shi, Y. Wang, H. Yang, X. Yan, X. Luo, H. Jiang, and W. Zhu J. Med. Chem. 52 2009 2854
15. C. Beguin, M.R. Richards, J. Li, Y. Wang, W. Xu, L.Y. Liu-Chen, W.A. Carlezon, and B.M. Cohen Bioorg. Med. Chem. Lett. 16 2006 4679
16. G.S. Lal, G.P. Pez, R.J. Pesaresi, F.M. Prozonic, and H. Cheng J. Org. Chem. 64 1999 7048
17. L.D. Luca, G. Giacomelli, and A. Porcheddu Org. Lett. 4 2002 553
18. T.A. Munro, M.A. Rizzacasa, B.L. Roth, B.A. Toth, and F. Yan J. Med. Chem. 48 2005 345
19. R.V. Bikbulatov, J. Stewart, W. Jin, F. Yan, B.L. Roth, D. Ferreira, and J.K. Zjawiony Tetrahedron Lett. 49 2008 937
20. C. Beguin, K.K. Duncan, T.A. Munro, D.M. Ho, W. Xu, L.Y. Liu-Chen, W.A. Carlezon, and B.M. Cohen Bioorg. Med. Chem. 17 2009 1370
21. P.R. Skaanderup, C.S. Poulsen, L. Hyldtoft, M.R. Jørgensen, and R. Madsen Synthesis 12 2002 1721
22. K. Tidgewell, C.E. Groer, W.W. Harding, A. Lozama, M. Schmidt, A. Marquam, J. Hiemstra, J.S. Partilla, C.M. Dersch, R.B. Rothman, L.M. Bohn, and T.E. Prisinzano J. Med. Chem. 51 2008 2421
23. T. Toru, T. Okumara, and Y. Ueno J. Org. Chem. 55 1990 1277
24. W. Damm, B. Giese, J. Hartung, T. Hasskerl, K.N. Houk, O. Huter, and H. Zipse J. Am. Chem. Soc. 114 1992 4067