Synthesis of new opioid derivatives with a propellane skeleton and their pharmacology: Part 1

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 13, 2011, Pages 4104-4107

  Yamamoto, Naoshi ^a,c   Fujii, Hideaki ^a   Nemoto, Toru ^a   Nakajima, Ryo ^a   Momen, Shinobu ^b   Izumimoto, Naoki ^b   Hasebe, Ko ^b   Mochizuki, Hidenori ^b   Nagase, Hiroshi ^a  

^a KITASATO UNIVERSITY   (Japan)

^b TORAY INDUSTRIES INC   (Japan)

^c HOSHI UNIVERSITY   (Japan)

Author keywords

Selectivity; Opioid; Propellane; Torsion angle

Indexed keywords

17 CYCLOPROPYLMETHYLMORPHINAN; 3,4 DICHLORO N METHYL N [2 (1 PYRROLIDINYL)CYCLOHEXYL]BENZENEACETAMIDE METHANESULFONATE; KNT 42; KNT 43; MORPHINE; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; NALFURAFINE; OPIATE DERIVATIVE; OPIATE RECEPTOR; SYK 173; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG SYNTHESIS; MOUSE; NONHUMAN;

ANALGESICS, OPIOID; ANIMALS; BRIDGED COMPOUNDS; CELLS, CULTURED; MICE; MOLECULAR STRUCTURE; PROTEIN BINDING; RECEPTORS, OPIOID, KAPPA; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 79958723759     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.04.147     Document Type: Article

References (42)

1. Dhawan, B. N.; Cesselin, F.; Raghubir, R.; Reisine, T.; Bradley, P. B.; Portoghese, P. S.; Hamon, M. Pharmacol. Rev. 1996, 48, 567.
2. Fujii, H.; Nagase, H. Curr. Med. Chem. 2006, 13, 1109. and references cited therein.
3. Nagase, H.; Hayakawa, J.; Kawamura, K.; Kawai, K.; Takezawa, Y.; Matsuura, H.; Tajima, C.; Endo, T. Chem. Pharm. Bull. 1998, 46, 366.
4. Kawai, K.; Hayakawa, J.; Miyamoto, T.; Imamura, Y.; Yamane, S.; Wakita, H.; Fujii, H.; Kawamura, K.; Matsuura, H.; Izumimoto, N.; Kobayashi, R.; Endo, T.; Nagase, H. Bioorg. Med. Chem. 2008, 16, 9188.
5. Nemoto, T.; Fujii, H.; Narita, M.; Miyoshi, K.; Nakamura, A.; Suzuki, T.; Nagase, H. Bioorg. Med. Chem. Lett. 2008, 18, 6398.
6. Nagase, H.; Watanabe, A.; Nemoto, T.; Yamaotsu, N.; Hayashida, K.; Nakajima, M.; Hasebe, K.; Nakao, K.; Mochizuki, H.; Hirono, S.; Fujii, H. Bioorg. Med. Chem. Lett. 2010, 20, 121.
7. Nakao, K.; Mochizuki, H. Drugs Today 2009, 45, 323.
8. Nemoto, T.; Yamamoto, N.; Watanabe, A.; Fujii, H.; Hasebe, K.; Nakajima, M.; Mochizuki, H.; Nagase, H. Bioorg. Med. Chem. 2011, 19, 1205.
9. Nagase, H.; Fujii, H. Top. Curr. Chem. 2011, 299, 29.
10. Nagase, H.; Kawai, K.; Hayakawa, J.; Wakita, H.; Mizusuna, A.; Matsuura, H.; Tajima, C.; Takezawa, Y.; Endo, T. Chem. Pharm. Bull. 1998, 46, 1695.
11. Nagase, H.; Yajima, Y.; Fujii, H.; Kawamura, K.; Narita, M.; Kamei, J.; Suzuki, T. Life Sci. 2001, 68, 2227.
12. Nagase, H.; Osa, Y.; Nemoto, T.; Fujii, H.; Imai, M.; Nakamura, T.; Kanemasa, T.; Kato, A.; Gouda, H.; Hirono, S. Bioorg. Med. Chem. Lett. 2009, 19, 2792.
13. Nagase, H.; Nemoto, T.; Matsubara, A.; Saito, M.; Yamamoto, N.; Osa, Y.; Hirayama, S.; Nakajima, M.; Nakao, K.; Mochizuki, H.; Fujii, H. Bioorg. Med. Chem. Lett. 2010, 20, 6302.
14. Fujii, H.; Narita, M.; Mizoguchi, H.; Murachi, M.; Tanaka, T.; Kawai, K.; Tseng, L. F.; Nagase, H. Bioorg. Med. Chem. 2004, 12, 4133.
15. Lahti, R. A.; Von Voigtlander, P. F.; Barsuhn, C. Life Sci. 1982, 31, 2257.
16. Szmuszkovicz, J.; Von Voigtlander, P. F. J. Med. Chem. 1982, 25, 1125.
17. Lahti, R. A.; Mickelson, M. M.; McCall, J. M.; Von Voigtlander, P. F. Eur. J. Pharmacol. 1985, 109, 281.
18. Mucha, R. F.; Herz, A. Psychopharmacology 1985, 86, 274.
19. Millan, M. J. Trends Pharmacol. Sci. 1990, 11, 70.
20. Tsuji, M.; Takeda, H.; Matsumiya, T.; Nagase, H.; Narita, M.; Suzuki, T. Life Sci. 2001, 68, 1717.
21. Zukin, R. S.; Eghbali, M.; Olive, D.; Unterwald, E. M.; Tempel, A. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4061.
22. Clark, J. A.; Liu, L.; Price, M.; Hersh, B.; Edelson, M.; Pasternak, G. W. J. Pharmacol. Exp. Ther. 1989, 251, 461.
23. Nock, B. In The Pharmacology of Opioid Peptides; Tesng, L. F., Ed.; Harwood Academic: Singapore, 1995; pp 29-56.
24. Endoh, T.; Matsuura, H.; Tajima, A.; Izumimoto, N.; Tajima, C.; Suzuki, T.; Saitoh, A.; Suzuki, T.; Narita, M.; Tseng, L. F.; Nagase, H. Life Sci. 1999, 65, 1685.
25. Endoh, T.; Tajima, A.; Kamei, J.; Suzuki, T.; Narita, M.; Tseng, L. F.; Nagase, H. Eur. J. Pharmacol. 2000, 387, 133.
26. Tsuji, M.; Yamazaki, M.; Takeda, H.; Matsumiya, T.; Nagase, H.; Tseng, L. F.; Narita, M.; Suzuki, T. Eur. J. Pharmacol. 2000, 394, 91.
27. Mori, T.; Takeda, H.; Matsumiya, T.; Nagase, H.; Yamazaki, M.; Narita, M.; Suzuki, T. Life Sci. 2000, 66, PL353.
28. Mori, T.; Nomura, M.; Yoshizawa, K.; Nagase, H.; Narita, M.; Suzuki, T. Life Sci. 2004, 75, 2473.
29. Portoghese, P. S.; Nagase, H.; Lipkowski, A. W.; Larson, D. L.; Takemori, A. E. J. Med. Chem. 1988, 31, 836.
30. Watanabe, A.; Fujii, H.; Nakajima, M.; Hasebe, K.; Mochizuki, H.; Nagase, H. Bioorg. Med. Chem. Lett. 2009, 19, 2416.
31. Toll, L.; Berzetei-Gurske, I. P.; Polgar, W. E.; Brandt, S. R.; Adapa, I. D.; Rodriguez, L.; Schwartz, R. W.; Haggart, D.; O'Brien, A.; White, A.; Kennedy, J. M.; Craymer, K.; Farrington, L.; Auh, J. S. NIDA Res Monogr. 1998, 178, 440.
32. Nagase, H.; Yamamoto, N.; Nemoto, T.; Yoza, K.; Kamiya, K.; Hirono, S.; Momen, S.; Izumimoto, N.; Hasebe, K.; Mochizuki, H.; Fujii, H. J. Org. Chem. 2008, 73, 8093.
33. Carroll, F. I.; Chaudhari, S.; Thomas, J. B.; Mascarella, S. W.; Gigstad, K. M.; Deschamps, J.; Navarro, H. A. J. Med. Chem. 2005, 48, 8182.
34. Thomas, J. B.; Atkinson, R. N.; Rothman, R. B.; Fix, S. E.; Wayne Mascarella, S.; Ariane Vinson, N.; Xu, H.; Dersch, C. M.; Lu, Y.-F.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. J. Med. Chem. 2001, 44, 2687.
35. Carroll, F. I.; Melvin, M. S.; Nuckols, M. C.; Mascarella, S. W.; Navarro, H. A.; Thomas, J. B. J. Med. Chem. 2006, 49, 1781.
36. Li, F.; Gaob, L.; Yin, C.; Chen, J.; Liu, J.; Xie, X.; Zhang, A. Bioorg. Med. Chem. Lett. 2009, 19, 4603.
37. Kulinkovich, O. Eur. J. Org. Chem. 2004, 4517. and references cited therein.
38. Andrzej Wolan, A.; Six, Y. Tetrahedron 2010, 66, 15. and references cited therein.
39. The selectivity obtained by our binding assay method was likely to be lower. Some groups have reported that the j selectivity of nalfurafine was higher than our result.
40. Cowan et al. reported that the κ selectivity of nalfurafine was μ/κ = 69 and δ/κ = 2147. Wang, Y.; Tang, K.; Inan, S.; Siebert, D.; Holzgrabe, U.; Lee, D. Y. W.; Huang, P.; Li, J.-G.; Cowan, A.; Liu-Chen, L.-Y. J. Pharmacol. Exp. Ther. 2005, 312, 220.
41. According to Satoh et al., the κ selectivity of nalfurafine was μ/κ = 15 and δ/κ = 343. Seki, T.; Awamura, S.; Kimura, C.; Ide, S.; Sakano, K.; Minami, M.; Nagase, H.; Satoh, M. Eur. J. Pharmacol. 1999, 376, 159.
42. Nagase's unpublished results.