C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: A conformation-activity study

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 14, 1998, Pages 1813-1818

  Tsai, Ya Ching ^a   Liou, Jing Ping ^a   Liao, Richard ^a   Cheng, Chen Yu ^a   Tao, Pao Luh ^b  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL DEFENSE MEDICAL CENTER   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANALGESIC AGENT; OPIATE AGONIST; OPIATE DERIVATIVE;

ARTICLE; DRUG CONFORMATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; PAIN; STRUCTURE ACTIVITY RELATION;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PIPERIDINES; PROTEIN BINDING; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032555178     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00318-7     Document Type: Article

References (13)

1. 1. (a) Michne, W. F. Chemistry of Opiate Analgesics and Antagonists. In Analgesics: Neurochemical, Behavioral, and Clinical Perspectives; Kuhar, M; Pasternak, G. Eds.; Raven Press: New York, 1984; pp. 125-148.
2. (b) Reitz, A. B.; Jetter, M. C.; Wild, K. D.; Raffa, R. B. Annu. Repts. Med. Chem., 1995, 11-20.
3. 2. Cheng, C. Y.; Hsin, L. W.; Liou, J. P. Tetrahedron 1996, 52, 10935-10944.
4. 3. Cheng, C. Y.; Liou, J. P.; Lee, M. J. Tetrahedron Lett. 1997, 38, 4571-4574.
5. 4. Lawson, J. A.; Toll, J.; Polgar, W.; Uyeno, E. T.; Loewe, G. H. Eur. J. Med. Chem. 1991, 26, 775.
6. 5. Aceto, M. D.; Harris, L. S.; May, E. L. NIDA Res. Monogr. 1986, 67, 399.
7. 6. Mitsunobu, O. Synthesis 1981, 1.
8. + : 233.1416, found 233.1401.
9. 8. Barnett, C. J.; Copley-Merriman, C. R.; Maki, J. J. Org. Chem. 1989, 54, 4795.
10. 9. Cheng, C. Y.; Hsin, L. W.; Lin, Y. P.; Tao, P. L.; Jong, T. T. Bioorg. Med. Chem. 1996, 4, 73.
11. 10. The calculation was performed with an SGI Indy workstation (MIPs, R4400, 32 MB, Indy 8-bit). The software used via CHARMm, which was developed by Harvard University and is included in "Quanta 96". The minimization procedures included Steepest Descents and Conjugate Gradient.
12. 11. (a) Froimowitz, M. J. Med. Chem. 1982, 25, 1127.
13. (b) Loew, G. H.; Jester, J. R. J. Med. Chem. 1975, 18, 1051.