(Aminoalkyl)indole isothiocyanates as potential electrophilic affinity ligands for the brain cannabinoid receptor

Journal of Medicinal Chemistry

Volumn 39, Issue 10, 1996, Pages 1967-1974

  Yamada, Koichiro ^a,f   Rice, Kenner C ^a   Flippen Anderson, Judith L ^b   Eissenstat, Michael A ^c,h   Ward, Susan J ^c,g   Johnson, M Ross ^a,d   Howlett, Allyn C ^e  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

^c Dept of Preclinical Biostatistics   (United States)

^d Trimeris Inc   (United States)

^e SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^f MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

^g WYETH AYERST RESEARCH   (United States)

^h SAIC FREDERICK INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(4 ISOTHIOCYANATO 1 NAPHTHYL)[2 METHYL 1 [2 (4 MORPHOLINYL)ETHYL] 1H INDOL 3 YL]METHANONE; 1 NAPHTHYL[1 [2 (4 MORPHOLINYL)ETHYL] 1H INDOL 3 YL]METHANONE; 1 NAPHTHYL[6 ISOTHIOCYANATO 1 [2 (4 MORPHOLINYL)ETHYL] 1H INDOL 3 YL]METHANONE; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ADENYLATE CYCLASE; CANNABINOID RECEPTOR; DEACETYLLEVONANTRADOL; GUANINE NUCLEOTIDE BINDING PROTEIN; GUANOSINE TRIPHOSPHATE; ISOTHIOCYANIC ACID DERIVATIVE; PRAVADOLINE; ROLIPRAM; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; BRAIN MEMBRANE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG POTENCY; DRUG RECEPTOR BINDING; LIGAND BINDING; NONHUMAN; RAT; RECEPTOR AFFINITY;

EID: 0030001034     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950932r     Document Type: Article

References (27)

1. Bell, M. R.; D'Ambra, T. E.; Kumar, V.; Eissenstat, M. A.; Herrmann, J. L.; Wetzel, J. R.; Rosi, D.; Philion, R. E.; Daum, S. J.; Hlasta, D. J.; Kullnig, R. K.; Ackerman, J. H.; Haubrich, D. R.; Luttinger, D. A.; Baizman, E. R.; Miller, M. S.; Ward, S. J. Antinociceptive (Aminoalkyl)indoles. J. Med. Chem. 1991, 34, 1099-1110.
2. D'Ambra, T. E.; Estep, K. G.; Bell, M. R.; Eissenstat, M. A.; Josef, K. A.; Ward, S. J.; Haycock, D. A.; Baizman, E. R.; Casiano, F. M.; Beglin, N. C.; Chippari, S. M.; Grego, J. D.; Kullnig, R. K.; Daley, G. T. Conformationally Restrained Analogues of Pravadoline-Nanomolar Potent, Enantioselective, (Aminoalkyl)indole Agonists of the Cannabinoid Receptor. J. Med. Chem. 1992, 35, 124-135.
3. Eissenstat, M. A.; Bell, M. R.; D'Ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V.; Estep, K. G.; Olefirowicz, E. M.; Wetzel, J. R.; Alexander, M. D.; Weaver, J. D., III; Haycock, D. A.; Luttinger, D. A.; Casiano, F. M.; Chippari, S. M.; Kuster, J. E.; Stevenson, J. I.; Ward, S. J. (Aminoalkyl)indoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics. J. Med. Chem. 1995, 38, 3094-3105.
4. Haubrich, D. R.; Ward, S. J.; Baizman, E.; Bell, M. R.; Bradford, J.; Ferrari, R.; Miller, M.; Perrone, M.; Pierson, A. K.; Saelens, J. K.; Luttinger, D. Pharmacology of Pravadoline: A New Analgesic Agent. J. Pharmacol. Exp. Ther. 1990, 255, 511-522.
5. Ward, S. J.; Mastriani, D.; Casiano, F.; Arnold, R. Pravadoline: Profile in Isolated Tissue Preparations. J. Pharmacol. Exp. Ther. 1990, 255, 1230-1239.
6. Ward, S. J.; Baizman, E.; Bell, M.; Childers, S.; D'Ambra, T.; Eissenstat, M.; Estep, K.; Haycock, D.; Howlett, A.; Luttinger, D.; Miller, M.; Pacheco, M. (Aminoalkyl)indoles (AAIs): A New Route to the Cannabinoid Receptor? NIDA Res. Monogr. 1990, 105, 425-426.
7. Pacheco, M. C.; Childers, S. R.; Arnold, R.; Casiano, F.; Ward, S. J. (Aminoalkyl)indoles: Actions on Specific G-protein-linked Receptors. J. Pharmacol. Exp. Ther. 1991, 257, 170-183.
8. Kuster, J. E.; Stevenson, J. I.; Ward, S. J.; D'Ambra, T. E.; Haycock, D. A. (Aminoalkyl)indole Binding in Rat Cerebellum: Selective Displacement by Natural and Synthetic Cannabinoids. J. Pharmacol. Exp. Ther. 1993, 264, 1352-1363.
9. Mackie, K.; Hille, B. Cannabinoids Inhibit N-Type Calcium Channels in Neuroblastoma- Glioma Cells. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3825-3829.
10. Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of a Cannabinoid Receptor and Functional Expression of the Cloned cDNA. Nature 1990, 346, 561-564.
11. Gerard, C. M.; Mollereau, C.; Vassart, G.; Parmentier, M. Molecular Cloning of a Human Cannabinoid Receptor Which Is Also Expressed in Testis. Biochem. J. 1991, 279, 129-134.
12. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular Characterization of a Peripheral Receptor for Cannabinoids. Nature 1993, 365, 61-65.
13. Howlett, A. C.; Bidaut-Russell, M.; Devane, W. A.; Melvin, L. S.; Johnson, M. R.; Herkenham, M. The Cannabinoid Receptor-Biochemical, Anatomical and Behavioral Characterization. Trends Neurosci. 1990, 13, 420-423.
14. Abood, M. E.; Martin, B. R. Neurobiology of Marijuana Abuse. Trends Pharmacol. Sci. 1992, 13, 201-206.
15. Howlett, A. C. Pharmacology of Cannabinoid Receptors. Annu. Rev. Pharmacol. Toxicol. 1995, 35, 607-634.
16. Leuck, G. J.; Perkins, R. P.; Whitmore, F. C. The Mercuration of Naphthalic Acids. J. Am. Chem. Soc. 1929, 51, 1831.
17. 9-Tetrahydrocannabinol. J. Pharmacol. Exp. Ther. 1992, 263, 1118-1126.
18. Johnson, M. R.; Melvin, L. S. The Discovery of Nonclassical Cannabinoid Analgetics. In Cannabinoids as Therapeutic Agents; Mechoulam, R., Ed.; CRC Press: Boca Raton, FL, 1986; pp 121-145.
19. Razdan, R. K. Structure-Activity Relationships in Cannabinoids. Pharmacol. Rev. 1986, 38, 75-149.
20. Martin, B. R.; Compton, D. R.; Thomas, B. F.; Prescott, W. R.; Little, P. J.; Razdan, R. K.; Johnson, M. R.; Melvin, L. S.; Mechoulam, R.; Ward, S. J. Behavioral, Biochemical, and Molecular Modeling Evaluations of Cannabinoid Analogs. Pharmacol. Biochem. Behav. 1991, 40, 471-478.
21. Melvin, L. S.; Milne, G. M.; Johnson, M. R.; Subramaniam, B.; Wilken, G. H.; Howlett, A. C. Structure-Activity Relationships for Cannabinoid Receptor-Binding and Analgesic Activity: Studies of Bicyclic Cannabinoid Analogs. Mol. Pharmacol. 1993, 44, 1008-1015.
22. Melvin, L. S.; Milne, G. M.; Johnson, M. R.; Wilken, G. H.; Howlett, A. C. Structure-Activity Relationships for Cannabinoid Receptor Binding and Analgesic Activity: Studies Leading to the Development of the ACD-Triyclic Cannabinoids. Drug Des. Discovery 1995, 13, 155-166.
23. Savarese, T. M.; Fraser, C. M. In Vitro Mutagenesis and the Search for Structure Function Relationships Among G Protein-Coupled Receptors. Biochem. J. 1992, 283, 1-19.
24. Hibert, M. F.; Trumpp-Kallmeyer, S.; Hoflack, J.; Bruinvels, A. This is Not a G Protein-Coupled Receptor. Trends Pharmacol. Sci. 1993, 14, 7-12.
25. Devane, W. A.; Dysarz, F. A., 3rd.; Johnson, M. R.; Melvin, L. S.; Howlett, A. C. Determination and Characterization of a Cannabinoid Receptor in Rat Brain. Mol. Pharmacol. 1988, 34, 605-613.
26. 3H]-CP-55,940 Binding to the Cannabinoid Receptor in Brain. Biotech Update 1991, 6, 21.
27. Howlett, A. C. Cannabinoid Inhibition of Adenylate Cyclase. Biochemistry of the Response in Neuroblastoma Cell Membranes. Mol. Pharmacol. 1986, 27, 429-436.