Synthesis and evaluation of 3-aminopropionyl substituted fentanyl analogues for opioid activity

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 18, 2006, Pages 4946-4950

  Petrov, Ravil R ^a   Vardanyan, Ruben S ^a   Lee, Yeon S ^a   Ma, Shou wu ^b   Davis, Peg ^b   Begay, Lucinda J ^a   Lai, Josephine Y ^b   Porreca, Frank ^b   Hruby, Victor J ^a  

^a University of Arizona   (United States)

^b UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

Author keywords

Enkephalin analogue; Fentanyl derivatives; Opioid agonists

Indexed keywords

1 (2 PHENETHYL) 4 (N ANILINO)PIPERIDINE; AMINOFENTANYL; BETA ALANINYL CHLORIDE; BIPHALIN; CARBOXYFENTANYL; CHLORINE DERIVATIVE; FENTANYL; FENTANYL DERIVATIVE; HYDRAZINE; ISOCYANATE; OPIATE; OPIATE RECEPTOR; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; GUINEA PIG; ILEUM; MYENTERIC PLEXUS; NONHUMAN; STRUCTURE ACTIVITY RELATION; VAS DEFERENS;

ANIMALS; FENTANYL; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NARCOTICS; PICOLINES; RATS; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746847693     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.040     Document Type: Article

References (42)

1. Janssen, P. A. J.; Gardocki, J. F. U.S. Patent 3141823, 1964.
2. Janssen, P. A. J., Fr. Patent M2430, 1964.
3. Riley T.N., Hale D.B., and Wilson M.C. J. Pharm. Sci. 62 (1973) 983
4. Janssen, P. A. J.; Van Daele, G. H. P. Deutch. Patent 2610228, 1976.
5. Leysen J.E., Laduron P.M., and Niemegeers C.J.E. In: Van Ree J., and Terenius L. (Eds). Characteristics and Function of Opioids (1978), Elsevier, North Holland 479-482
6. Van Bever W.F.M., Niemegeers C.J.E., Schellekens K.H.L., and Janssen P.A.J. Arzneim.-Forsch. 26 (1976) 1548
7. Janssen, P. A. J.; Van Daele, G. H. P. U.S. Patent 4179569, 1979.
8. Fang S.N., Ge B.J., Dai Q.Y., Li Q.Z., Zhou D.H., Ni C.H., Wu R.Q., and Huang Z.M. Acta Pharm. Sin. 18 (1983) 823
9. Huang, B. S.; Deutsche, K. H.; Lalinde, N. L.; Terrell, R. C.; Kudzma, L. V. Eur. Patent 160422, 1985.
10. Janssens F., Torremans J., and Janssen P.A.J. J. Med. Chem. 29 (1986) 2290
11. Kudzma, L. V.; Spencer, H. K.; Severnak, S. A. U.S. Patent 4791121, 1988.
12. Vartanyan, S. A.; Vartanyan, R. S.; Zhamagortsyan, V. N.; Martirosyan, V. O.; Vlasenko, V.; Azlivyan, A. S.; Durgaryan, L. K. U.S. Patent 736583, 1985.
13. Vartanyan R.S., Martirosyan V.O., Vartanyan S.A., Vlasenko E.V., Durgaryan L.K., and Azlivyan A.S. Khim.-Farmatsevticheskii Zh. 23 (1989) 562
14. Vartanyan R.S., Martirosyan V.O., Vartanyan S.A., Engoyan A.P., Vlasenko E.V., Durgaryan L.K., Azlivyan A.S., and Val'dman A.V. Khim.-Farmatsevticheskii Zh. 23 (1989) 573
15. Bagley, J. R.; Spencer, K. H. Eur. Patent 277794, 1988.
16. Bagley J.R., Wynn R.L., Rudo F.G., Doorley B.M., Spencer H.K., and Spaulding T. J. Med. Chem. 32 (1989) 663
17. Rothman R.B., Xu H., Seggel M., Jacobson A.E., Rice K.C., Brine G.A., and Carroll F.I. Life Sci. 48 (1991) 111
18. Lalinde N., Moliterni J., Wright D., Spencer H.K., Ossipov M.H., Spaulding T.C., and Rudo F.G. J. Med. Chem. 33 (1990) 2876
19. Feldman P.L., James M.K., Brackeen M.F., Bilotta J.M., Schuster S.V., Lahey A.P., Lutz M.W., Johnson M.R., and Leighton H.J. J. Med. Chem. 34 (1991) 2202
20. Feldman, P. L.; James, M. K.; Brackeen, M. F.; Johnson, M. R.; Leighton, H. J. Eur. Patent 383579, 1990.
21. Bowdle T.A. Drug Saf. 19 (1998) 173
22. Essawi M.Y.H., and Portoghese P.S. J. Med. Chem. 26 (1983) 348
23. Schiller P.W., Nguyen T.M.D., Chung N.N., and Lemieux C. J. Med. Chem. 32 (1989) 698
24. Schiller P.W., Weltrowska G., Nguyen T.M.D., Lemieux C., Chung N.N., and Lu Y. Life Sci. 73 (2003) 691
25. Lee K., Jung W.-H., Park C.W., Hong C.Y., Kim I.C., Kim S., Oh Y.S., Kwon O.H., Lee S.-H., Park H.D., Kim S.W., Lee Y.H., and Yoo Y.J. Bioorg. Med. Chem. Lett. 18 (1998) 2563
26. McConnell, R. I.; Benchikh, E. O.; Fitzgerald, S. P.; Lamont, J. V. Eur. Patent 1312923, 2003.
27. Maryanoff B.E., Simon E.J., Gioannini T., and Gorissens H. J. Med. Chem. 25 (1982) 913
28. +; HRMS calcd: 481.2365; found: 481.2437.
29. +; HRMS calcd: 351.2311; found: 351.2375.
30. +; HRMS calcd: 447.2134; found: 447.2221.
31. +; HRMS calcd: 422.2682; found: 422.2752.
32. Petrov R.R., Vardanyan R.S., Nichol G.S., Carducci M.D., Ma S.-W., Lai J.Y., and Hruby V.J. Acta Cryst. E62 (2006) o2815
33. Stephen W.H. Org. Proc. Dev. 3 (1999) 241
34. +; HRMS calcd: 540.3100; found: 540.3157.
35. 3.
36. +; HRMS calcd: 789.4214; found: 789.4271.
37. Polt R., Porreca F., Szabo L., Bilsky E.J., Davis T.P., Horvath R., Abbruscato T.J., Yamamura H.J., and Hruby V.J. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 7114
38. Misicka A., Lipkowski A.W., Horvath R., Davis P., Kramer T.H., Yamamura H.I., and Hruby V.J. Life Sci. 51 (1992) 1025
39. Yeadon M., and Kitchen I. Neuropharmacology 27 (1988) 345
40. Lipkowski A.W., Misicka A., Davis P., Stropova D., Janders J., Lachwa M., Porreca F., Yamamura H.I., and Hruby V.J. Bioorg. Med. Chem. Lett. 9 (1999) 2763
41. Kramer T.H., Davis P., Hruby V.J., Burks T.F., and Porreca F. J. Pharmacol. Exp. Ther. 266 (1993) 577
42. Montero A., Goya P., Jagerovic N., Callado L.F., Meana J.J., Giron R., Goicoechea C., and Martin M.I. Bioorg. Med. Chem. 10 (2002) 1009