Syntheses of novel pyridazinomorphinans by inverse electron demand cycloaddition and their binding to μ and κ receptors

Archiv der Pharmazie

Volumn 330, Issue 6, 1997, Pages 163-168

  Klindert, Thilo ^a   Stroetmann, Isabel ^a   Seitz, Gunther ^a   Höfner, Georg ^b   Wanner, Klaus Th ^b   Frenzen, Gerlinde ^c   Eckhoff, Brigitta ^c  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

^c UNIVERSITY OF KASSEL   (Germany)

Author keywords

1,2,4,5 tetrazines; Diels Alder reactions, inverse; opioid analgesics; pyridazinomorphinans; pyrrolomorphinans

Indexed keywords

CODEINE; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; KAPPA OPIATE RECEPTOR; MORPHINAN DERIVATIVE; MU OPIATE RECEPTOR; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; PYRIDAZINE DERIVATIVE;

ANIMAL TISSUE; ARTICLE; BRAIN; CATTLE; CONTROLLED STUDY; CORPUS STRIATUM; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; RAT; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; BENZENEACETAMIDES; BINDING, COMPETITIVE; CATTLE; CELL MEMBRANE; CORPUS STRIATUM; CRYSTALLOGRAPHY, X-RAY; ENKEPHALIN, ALA(2)-MEPHE(4)-GLY(5)-; ENKEPHALINS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MORPHINANS; PYRAZINES; PYRROLIDINES; RADIOLIGAND ASSAY; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU;

EID: 0030765505     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/ardp.19973300602     Document Type: Article

References (25)

1. For leading references see: a) K. W. Bentley in The Alkaloids (Ed.: R. H. F. Manske) Academic Press, New York 1971, Vol. XIII, p. 75; b) A. F. Casy, R. T. Parfitt, Opioid Analgesics. Plenum Press, New York 1986, p.69; c) L. L. Knipmeyer, H. Rapoport, J. Med. Chem. 1985, 28, 461-466; d) U. Pindur, D. Keilhofer, Liebigs Ann. Chem. 1993, 947-953.
2. For leading references see: a) K. W. Bentley in The Alkaloids (Ed.: R. H. F. Manske) Academic Press, New York 1971, Vol. XIII, p. 75; b) A. F. Casy, R. T. Parfitt, Opioid Analgesics. Plenum Press, New York 1986, p.69; c) L. L. Knipmeyer, H. Rapoport, J. Med. Chem. 1985, 28, 461-466; d) U. Pindur, D. Keilhofer, Liebigs Ann. Chem. 1993, 947-953.
3. For leading references see: a) K. W. Bentley in The Alkaloids (Ed.: R. H. F. Manske) Academic Press, New York 1971, Vol. XIII, p. 75; b) A. F. Casy, R. T. Parfitt, Opioid Analgesics. Plenum Press, New York 1986, p.69; c) L. L. Knipmeyer, H. Rapoport, J. Med. Chem. 1985, 28, 461-466; d) U. Pindur, D. Keilhofer, Liebigs Ann. Chem. 1993, 947-953.
4. For leading references see: a) K. W. Bentley in The Alkaloids (Ed.: R. H. F. Manske) Academic Press, New York 1971, Vol. XIII, p. 75; b) A. F. Casy, R. T. Parfitt, Opioid Analgesics. Plenum Press, New York 1986, p.69; c) L. L. Knipmeyer, H. Rapoport, J. Med. Chem. 1985, 28, 461-466; d) U. Pindur, D. Keilhofer, Liebigs Ann. Chem. 1993, 947-953.
5. P. S. Portoghese, H. Nagase, A. W. Lipkowski, D. L. Larson, A. E. Takemori, J. Med. Chem. 1988, 31, 836-841; S. L. Olmsted, A. E. Takemori, P. S. Portoghese, J. Med. Chem. 1993, 36, 179-180.
6. P. S. Portoghese, H. Nagase, A. W. Lipkowski, D. L. Larson, A. E. Takemori, J. Med. Chem. 1988, 31, 836-841; S. L. Olmsted, A. E. Takemori, P. S. Portoghese, J. Med. Chem. 1993, 36, 179-180.
7. a) P. S. Portoghese, M. Sultana, A. E. Takemori, J. Med. Chem. 1990, 33, 1714-1720;
8. b) P. S. Portoghese, H. Nagase, K. E. Maloney Huss, C.-E. Lin, A. E. Takemori, J. Med. Chem. 1991, 34, 1715-1720 ;
9. c) P. Schwarz, H. Schmidhammer, Heterocycles, 1994, 39, 35-38.
10. R. A. Carboni, R. V. Lindsey, J. Am. Chem. Soc. 1959, 81, 4342-4346.
11. 5a) D. L. Boger, Tetrahedron 1983, 39, 2869-2939;
12. 5b) D. L. Boger, Chem. Rev. 1986, 86, 781-793;
13. D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, INC. New York 1987.
14. F. Thalhammer, U. Wallfahrer, J. Sauer, Tetrahedron Lett. 1990, 31, 6851-6854.
15. K.-A. Kovar, F. Schielein, Arch. Pharm. (Weinheim), 1978, 311, 73-75; I. Seki, Yakugaku Zasshi, 1964, 84, 621-625.
16. K.-A. Kovar, F. Schielein, Arch. Pharm. (Weinheim), 1978, 311, 73-75; I. Seki, Yakugaku Zasshi, 1964, 84, 621-625.
17. N. J. Bach, E. C. Kornfeld, N. D. Jones, M. O. Chaney, D. E. Dorman, J. W. Paschal, J. A. Clemens, E. W. Smalstig, J. Med. Chem. 1980, 23, 481-491.
18. D. L. Boger, R. S. Coleman, J. S. Panek, D. Yohames, J. Org. Chem. 1984, 49, 4405-4409.
19. 1H-NMR spectra were confirmed by analysing a CH-COSY
20. Further details of the crystal structure investigation are available from the Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen, on quoting the depository number CSD-406351.
21. Program used: SHELXS-86 (G. M. Sheldrick, Göttingen 1990).
22. Program used: SHELXL-93 (G. M. Sheldrick, Göttingen 1993); drawings: SCHAKAL 92 (Keller, Freiburg, 1992) and ZORTEP [L. Zsolnai, Heidelberg, 1996].
23. Program used: SHELXL-93 (G. M. Sheldrick, Göttingen 1993); drawings: SCHAKAL 92 (Keller, Freiburg, 1992) and ZORTEP [L. Zsolnai, Heidelberg, 1996].
24. Program used: SHELXL-93 (G. M. Sheldrick, Göttingen 1993); drawings: SCHAKAL 92 (Keller, Freiburg, 1992) and ZORTEP [L. Zsolnai, Heidelberg, 1996].
25. For experimental details of the tests see: K. Th. Wanner, J. Praschak, G. Höfner, H. Beer, Arch. Pharm. Pharm. Med. Chem. 1996, 329, 11-22.