Design and synthesis of a library of tertiary amides: Evaluation as mimetics of the melanocortins' active core

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 17, 2007, Pages 5787-5810

  Mutulis, Felikss ^a   Kreicberga, Jana ^a   Yahorava, Sviatlana ^a   Mutule, Ilze ^a   Borisova Jan, Larisa ^a   Yahorau, Aleh ^a   Muceniece, Ruta ^a   Azena, Sandra ^a   Veiksina, Santa ^a   Petrovska, Ramona ^a   Wikberg, Jarl E S ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Indole derivatives; Melanocortin receptor ligands; Solid phase organic synthesis; Tertiary amides

Indexed keywords

ACETIC ACID; ALDEHYDE; AMIDE; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; CARBOXYLIC ACID; CYCLIC AMP; DIAMINE; ETHYLAMINE; ETHYLENE GLYCOL; FORMIC ACID DERIVATIVE; INDOLE DERIVATIVE; KETONE; MELANOCORTIN; MELANOCORTIN 1 RECEPTOR; MELANOCORTIN 3 RECEPTOR; MELANOCORTIN 4 RECEPTOR; MELANOCORTIN 5 RECEPTOR; MELANOCORTIN RECEPTOR; POLYMER; RECEPTOR BLOCKING AGENT; RECEPTOR SUBTYPE; RECOMBINANT PROTEIN; RESIN; SCHIFF BASE; SODIUM BOROHYDRIDE; TERTIARY AMIDE; TITANIUM TETRACHLORIDE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; ALKYLATION; ANIMAL CELL; ARTICLE; CHIRAL CHROMATOGRAPHY; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; RECEPTOR AFFINITY; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOLID PHASE SYNTHESIS;

ALPHA-MSH; AMIDES; ANIMALS; BINDING SITES; BIOMIMETICS; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIC AMP; DRUG DESIGN; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MELANOCORTINS; MELANOMA; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34447284286     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.06.003     Document Type: Article

References (70)

1. Nakanishi S., Inoue A., Kita T., Nakamura M., Chang A.C., Cohen S.N., and Numa S. Nature 278 (1979) 423-427
2. Chhajlani V., and Wikberg J.E.S. FEBS Lett. 309 (1992) 417-420
3. Mountjoy K., Robbins L.S., Mortrud M.T., and Cone R.D. Science 257 (1992) 1248-12451
4. Gantz I., Konda Y., Tashiro T., Shimoto Y., Miwa H., Munzert G., Watson S.J., Delvalle J., and Yamada T. J. Biol. Chem. 268 (1993) 8246-8250
5. Gantz I., Miwa H., Konda Y., Shimoto Y., Tashiro T., Watson S.J., Delvalle J., and Yamada T. J. Biol. Chem. 268 (1993) 15174-15179
6. Chhajlani V., Muceniece R., and Wikberg J.E.S. Biochem. Biophys. Res. Commun. 195 (1993) 866-873
7. Gantz I., Shimoto Y., Konda Y., Miwa H., Dickinson C.J., and Yamada T. Biochem. Biophys. Res. Commun. 200 (1994) 1214-1220
8. Prusis P., Frandberg P.-A., Muceniece R., Kalvinsh I., and Wikberg J.E.S. Biochem. Biophys. Res. Commun. 210 (1995) 205-210
9. Haskell-Luevano C., Sawyer T.K., Trumpp-Kallmeyer S., Bikker J., Humblet C., Gantz I., and Hruby V.J. Drug Des. Discov. 14 (1996) 197-211
10. Suzuki I., Cone R.D., Im S., Bordlund J., and Abdel-Malek Z.A. Endocrinology 137 (1996) 1627-1633
11. Xia Y., Wikberg J.E.S., and Chhajlani V. NeuroReport 6 (1995) 2193-2196
12. Rajora N., Ceriani G., Catania A., Star R.A., Murphy M.T., and Lipton J.M. J. Leukoc. Biol. 59 (1996) 248-253
13. Klungland H., Vaage D.I., Gomez-Raya L., Adalsteinsson S., and Lien S. Mamm. Genome 6 (1995) 636-639
14. Ignar D.M., Andrews J.L., Jansen M., Eilert M.M., Pink H.M., Lin P., Sherrill R.G., Szewczyk J.R., and Conway J.G. Peptides 24 (2003) 709
15. Weber A., Kapas S., Hinson J., Grant D.B., Grossman A., and Clark J.L. Biochem. Biophys. Res. Commun. 197 (1993) 172-178
16. Kesterson R.A. In: Cone R.D. (Ed). The Melanocortin Receptors (2000), Humana Press, Totowa, New Jersey 385-403
17. Cone R.D. In: Cone R.D. (Ed). The Melanocortin Receptors (2000), Humana Press, Totowa, New Jersey 405-447
18. Chen W. In: Cone R.D. (Ed). The Melanocortin Receptors (2000), Humana Press, Totowa, New Jersey 449-472
19. Kask A., Rägo L., Mutulis F., Pähkla R., Wikberg J.E.S., and Schiöth H.B. Biochem. Biophys. Res. Commun. 245 (1998) 90-93
20. Adan R.A.H., Nijenhuis W.A.J., and Kas M.J.H. Int. Congr. Ser. 1249 (2003) 195-206
21. Haskell-Luevano C., Sawyer T.K., Hendrata S., North C., Panahinia L., Stum M., Staples D.J., De Lauro Castrucci A.M., Hadley M.E., and Hruby V.J. Peptides 17 (1996) 995-1002
22. Sawyer T.K., Sanfilippo P.J., Hruby V.J., Engel M.H., Heward C.B., Bernet J.B., and Hadley M.E. Proc. Natl. Acad. Sci. U.S.A. 77 (1980) 5754-5758
23. Schiöth H.B., Mutulis F., Muceniece R., Prusis P., and Wikberg J.E.S. Br. J. Pharmacol. 124 (1998) 75-82
24. Hruby V.J., Lu D., Sharma S.D., de Castrucci A., Kesterson R.A., Al-Obeidi F.A., Hadley M.E., and Cone R.D. J. Med. Chem. 38 (1995) 3454-3461
25. Szardenings M., Törnroth S., Mutulis F., Muceniece R., Keinänen K., Kuusinen A., and Wikberg J.E.S. J. Biol. Chem. 272 (1997) 27943-27948
26. Sebhat I.K., Martin W.J., Ye Z., Barakat K., Mosley R.T., Johnston D.B.R., Bakshi R., Palucki B., Weinberg D.H., MacNeil T., Kalyani R.N., Tang R., Stearns R.A., Miller R.R., Tamvakopoulos C., Strack A.M., McGowan E., Cashen D.E., Drisko J.E., Hom G.J., Howard A.D., MacIntyre D.E., van der Ploeg L.H.T., Patchett A.A., and Nargund R.P. J. Med. Chem. 45 (2002) 4589-4593
27. Mutulis F., Yahorava S., Mutule I., Yahorau A., Kopanchuk S., Veiksina S., Rinken A., and Wikberg J.E.S. J. Label. Compd. Rad. 46 (2003) 1007-1017
28. Mutulis F., Yahorava S., Mutule I., Yahorau A., Liepinsh E., Kopantshuk S., Veiksina S., Tars K., Belyakov S., Mishnev A., Rinken A., and Wikberg J.E.S. J. Med. Chem. 47 (2004) 4613-4626
29. Chaki S., Hirota S., Funakoshi T., Suzuki Y., Suetake S., Okubo T., Ishii T., Nakazato A., and Okuyama S. J. Pharmacol. Exp. Ther. 304 (2003) 818-826
30. Chen C., Yu J., Fleck B.A., Hoare S.R.J., Saunders J., and Foster A.C. J. Med. Chem. 47 (2004) 4083-4088
31. Hruby V.J., Wilkes B.C., Cody W.L., Sawyer T.K., and Hadley M.E. Peptide Protein Rev. 3 (1984) 1-64
32. Nikiforovich G.V., Sharma S.D., Hadley M.E., and Hruby V.J. Biopolymers 46 (1998) 155-167
33. Al-Obeidi F., O'Connor S.D., Job C., Hruby V.J., and Pettitt B.M. J. Pept. Res. 51 (1998) 420-431
34. Lee J.-H., Lim S.-K., Huh S.-H., Lee D., and Lee W. Eur. J. Biochem. 257 (1998) 31-40
35. Haskell-Luevano C., Rosenquist Å., Souers A., Khong K.C., Ellman J.A., and Cone R.D. J. Med. Chem. 42 (1999) 4380-4387
36. Kulesza A., Ebetino F.H., Mishra R.K., Cross-Doersen D., and Mazur A.W. Org. Lett. 5 (2003) 1163-1166
37. Heizmann G., Hildebrand P., Tanner H., Ketterer S., Pansky A., Froidevaux S., Beglinger C., and Eberle A.N. J. Recep. Signal Transduction Res. 19 (1999) 449-466
38. Mutulis F., Mutule I., Liepinsh E., Yahorau A., Lapinsh M., Kopantshuk S., Veiksina S., Rinken A., and Wikberg J.E.S. Peptides 26 (2005) 1997-2016
39. Thompson D.A., Chai B.-X., Rood H.L.E., Siani M.A., Douglas N.R., Gantz I., and Millhauser G.L. Bioorg. Med. Chem. Lett. 13 (2003) 1409-1413
40. Joseph C.G., Bauzo R.M., Xiang Z., and Haskell-Luevano C. Bioorg. Med. Chem. Lett. 13 (2003) 2079-2082
41. Mutulis F., Mutule I., Lapins M., and Wikberg J.E.S. Bioorg. Med. Chem. Lett. 12 (2002) 1035-1038
42. Mutulis F., Mutule I., and Wikberg J.E.S. Bioorg. Med. Chem. Lett. 12 (2002) 1039
43. Haskell-Luevano C. In: Cone R.D. (Ed). The Melanocortin Receptors (2000), Humana Press, Totowa, New Jersey 263-306
44. Chai B.-X., Pogozheva I.D., Lai Y.-M., Li J.-Y., Neubig R.R., Mosberg H.I., and Gantz I. Biochemistry 44 (2005) 3418-3431
45. Moehrle H., Ehrhardt H., Kilian R., and Spillmann P. Archiv Pharm. Bericht. 303 (1970) 531
46. Adam, K.; Joschek, H.I.; Hoffmann, H. Ger.Offen. DE 2038023, 1972.
47. Chem. Abstr. 76 (1972) 112790h
48. Barkdoll A.E., Gray H.W., and Kirk Jr. W. J. Am. Chem. Soc. 73 (1951) 741-746
49. Look G.C., Murphy M.M., Campbell D.A., and Gallop M.A. Tetrahedron Lett. 36 (1995) 2937-2940
50. Szardenings A.K., Burkoth T.S., Look G.C., and Campbell D.A. J. Org. Chem. 61 (1996) 6720-6722
51. Salvi J.-P., Walchshofer N., and Paris J. Tetrahedron Lett. 35 (1994) 1181-1184
52. Coste J., Frerot E., Jouin P., and Castro B. Tetrahedron Lett. 32 (1991) 1967-1970
53. King D.S., Fields C.G., and Fields G.B. Int. J. Pept. Prot. Res 36 (1990) 255-266
54. Mutulis F., Erdélyi M., Mutule I., Kreicberga J., Yahorava S., Yahorau A., Borisova-Jan L., and Wikberg J.E.S. Molecules 8 (2003) 728-734
55. Barker D., McLeod M.D., Brimble M.A., and Savage G.P. Tetrahedron Lett. 42 (2001) 1785-1788
56. Bernatowicz M.S., Wu Y., and Matsueda G.R. J. Org. Chem. 57 (1992) 2497-2502
57. Barney C.L., Huber E.W., and McCarthy J.R. Tetrahedron Lett. 31 (1990) 5547-5550
58. Natale N.R., and Hutchins R.O. Org. Prep. Proced. Int. 9 3-4-5 (1977) 103-108
59. Holder J.R., Bauzo R.M., Xiang Z., and Haskell-Luevano C. J. Med. Chem. 45 (2002) 3073-3081
60. Conde-Frieboes, K.W.; Ankersen, M.; Sensfuss, U.; Wulff, B.S.; Thogersen, H.; Lustenberger, P.; Rudolf, K.; Krist, B.; Mueller, S.; Stenkamp, D.; Schindler, M.; Wieland, H.; Arndt, K. PCT Int. Appl. WO 2004048345 A2, 2004.
61. Chem. Abstr. 141 (2004) 38848
62. Tian X., Field T., Mazur A.W., Ebetino F.H., Wos J.A., Crossdoersen D., Pinney B.B., and Sheldon R.J. Bioorg. Med. Chem. Lett. 15 (2005) 2819-2823
63. Sharma, S.D.; Shi, Y.-Q.; Wu, Z.; Rajpurohit, R.U.S. Pat. Appl. Publ. 2004/0152134 A1, 2004.
64. Chem. Abstr. 141 (2004) 151030
65. Sharma, S.D.; Shi, Y.-Q.; Wu, Z.; Rajpurohit, R.U.S. Pat. Appl. Publ. 2004/0157264, 2004.
66. Chem. Abstr. 141 (2004) 191073
67. Sharma, S.D.; Shadiack, A.M.; Shi, Y.-Q.; Wu, Z.; Rajpurohit, R.; Burris, K.; Purma, P.U.S. Pat. Appl. Publ. 2005/0130988 A1, 2005; Chem. Abstr. 2005, 143, 20084.
68. Schiöth H.B., Muceniece R., Wikberg J.E.S., and Chhajlani V. Eur. J. Pharmacol., Mol. Pharmacol. Sect. 288 (1995) 311-317
69. Schiöth H.B., Muceniece R., and Wikberg J.E.S. Pharmacol. Toxicol. 79 (1996) 161-165
70. Nordstedt C., and Fredholm B.B. Anal. Chem. 189 (1990) 231-234