Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans - Further SAR of levorphanol

Journal of Medicinal Chemistry

Volumn 50, Issue 11, 2007, Pages 2747-2751

  Zhang, Ao ^a   Li, Fuying ^a   Ding, Chunyong ^a,d   Yao, Qizhen ^d   Knapp, Brian I ^b   Bidlack, Jean M ^b   Neumeyer, John L ^c  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b UNIVERSITY OF ROCHESTER SCHOOL OF MEDICINE AND DENTISTRY   (United States)

^c MCLEAN HOSPITAL   (United States)

^d CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

6,7 INDOLO MORPHINAN DERIVATIVE; 6,7 THIAZOLO MORPHINAN DERIVATIVE; DELTA OPIATE RECEPTOR; LEVORPHANOL; MORPHINAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

ANALGESICS, OPIOID; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; INDOLES; LEVORPHANOL; RADIOLIGAND ASSAY; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 34250201803     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0701674     Document Type: Article

References (18)

1. Eguchi, M. Recent Advances in Selective Opioid Receptor Agonists and Antagonists. Med. Res. Rev. 2004, 24, 182-212.
2. Aldrich, J. V.; Vigil-Cruz, S. C. Narcotic Analgesics. In Burger's Medicinal Chemistry and Drug Discovery; Abraham, D., Ed.; John Wiley & Sons: New York, 2003; p 329.
3. Fries, D. S. Opioid Analgesics. In Foye's Principles of Medicinal Chemistry; Williams, D. A., Lemke, T. L., Eds.; Lippincott Williams & Wilkins: PA, 2002; p 453.
4. Neumeyer, J. L.; Zhang, A.; Xiong, W.; Gu, X.; Hilbert, J. E.; Knapp, B. I.; Negus, S. S.; Mello, N. K.; and Bidlack, J. M. Design and Synthesis of Novel Bivalent Morphinan Ligands for Opioid Receptors. J. Med. Chem. 2003, 46, 5162-5170.
5. Zhang, A.; Xiong, W.; Bidlack, J. M.; Hilbert, J. E.; Knapp, B. I.; Wentland, M. P.; Neumeyer, J. L. 10-Ketomorphinan and 3-Substituted-3- desoxymorphinan Analogues as Mixed κ and μ Opioid Ligands: Synthesis and Biological Evaluation of Their Binding Affinity at Opioid Receptors. J. Med. Chem. 2004, 47, 165-174.
6. Zhang, A.; Xiong, W.; Hilbert, J. E.; DeVita, E. K.; Bidlack, J. M.; Neumeyer, J. L. 2-Aminothiazole-Derived Opioids - Bioisosteric Replacement of Phenols. J. Med. Chem. 2004, 47, 1886-1888.
7. Portoghese, P. S.; Sultana, M.; Takemori, A. E. Design of Peptidomimetic δ Opioid Receptor Antagonist Using The Message-Address Concept. J. Med. Chem. 1990, 33, 1714-1720.
8. Coop, A.; Rothman, R. B.; Dersch, C.; Partilla, J.; Porreca, F.; Devis, P.; Jacobson, A. E.; Rice, K. C. δ Opioid Affinity and Selectivity of 4-Hydroxy-3-methoxyindolomorphinan Analogues Related to Naltrindole. J. Med. Chem. 1999, 42, 1673-1679.
9. Coop, A.; Rice, K. Direct and Simple Conversion of Codeine to Thebainone-A and Dihydrothebainone. Heterocycles 1999, 50, 39-42.
10. Sawa, Y. K.; Tsuji, N.; Maeda, S. Elimination of the 4-Hydroxyl Group of the Alkaloids Related to Morphine. I. Tetrahedron 1961, 15, 144-153.
11. Sawa, Y. K.; Tsuji, N.; Maeda, S. Elimination of the 4-Hydroxyl Group of the Alkaloids Related to Morphine. II. Tetrahedron 1961, 15, 154-159.
12. Sawa, Y. K.; Tsuji, N.; Okabe, K.; Miyamoto, T. Elimination of the 4-Hydroxyl Group of the Alkaloids Related to Morphine. VI. Synthesis of (-)-3-Hydroxy-N-methyl-C-nor-morphinan derivatives. Tetrahedron 1965, 21, 1121-1128.
13. Sawa, Y. K.; Horiuchi, M. Elimination of the 4-Hydroxyl Group of the Alkaloids Related to Morphine. Synthesis of (-)-3-Methoxy-N- methylisomorphinan Derivatives. Tetrahedron 1965, 21, 1133-1139.
14. Sawa, Y. K.; Maeda, S. Elimination of the 4-Hydroxyl Group of the Alkaloids Related to Morphine. III. Tetrahedron 1964, 20, 2247-2253.
15. Olfoson, R. A.; Marts, J. T.; Seret, J. P.; Piteau, M.; Malfroot, T. A. A New Reagent for the Selective, High Yield N-Dealkylation of Tertiary Amines: Improved Synthesis of Naltrexone and Albuphine. J. Org. Chem. 1984, 49, 2081-2082.
16. Kubota, H.; Rothman, R. B.; Dersch, C.; McCullough, K.; Pinto, J.; Rice, K. C. Synthesis and Biological Activity of 3-Substituted 3-Desoxynaltrindole Derivatives. Bioorg. Med. Chem. Lett. 1998, 8, 799-804.
17. Katsuura, K.; Yamaguchi, K.; Sakai, S.-I.; Mitsuhashi, K. Thiazole Analogs of Benzomorphans. II. Synthesis of Novel Thiazolo[5,4-f]- morphans. Chem. Pharm. Bull. 1983, 31, 1518-1527.
18. Davidson, M. R.; Gregg, B. T. Improved Synthesis of Dihydrothebainone and its 14β-Isomer. Synth. Commun. 1998, 28, 547-558.