Synthesis of novel, potentially biologically active dibenzosuberone derivatives

Molecules

Volumn 10, Issue 12, 2005, Pages 1429-1437

  Merkaš, Sonja ^a   Litvić, Mladen ^a   Cepanec, Ivica ^a   Vinković, Vladimir ^b  

^a Belupo Ltd   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Amitriptiline; Bromination; Dibenzosuberone; Noxiptiline; Tricyclic antidepressants

Indexed keywords

DIBENZO[A,D]CYCLOHEPTENE DERIVATIVE; DIBENZSUBERONE; TRICYCLIC ANTIDEPRESSANT AGENT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANTIDEPRESSIVE AGENTS, TRICYCLIC; DIBENZOCYCLOHEPTENES; MOLECULAR STRUCTURE;

EID: 29844455551     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/10121429     Document Type: Article

References (30)

1. McQuay, H. J.; Moore R. A. Antidepressants and chronic pain. Br. Med. J. 1997, 314, 763-764.
2. Mertz, H. Psychotherapeutics and serotonin agonists and antagonists. J. Clin. Gastroenterol. 2005, 39, S247-S250.
3. Max, M. B.; Culnane, M.; Schafer, S. C.; Gracely, R. H.; Walter, D. J.; Smoller, B.; Dubner, R. Amitriptyline relieves diabetic neuropathy pain in patients with normal or depressed mood. Neurology 1987, 37, 589-596.
4. Williams, J. W.; Rost, K.; Dietrich, A. J.; Ciotti, M. C.; Zyzanski, S. J.; Cornell, J. Primary care physicians' approach to depressive disorders. Arch. Fam. Med. 1999, 8, 58-67.
5. Walsh, T. D. Antidepressants in chronic pain. Clin. Neuropharmacol. 1983, 6, 271-295.
6. Hoffsomer, R. D.; Taub, D.; Wendler, N. L. The Homoallylic Rearrangement in the Synthesis of Amitriptyline and Related Systems. J. Org. Chem. 1962, 27, 4134-4137.
7. Hoffsomer, R. D.; Taub, D.; Wendler, N. L. Synthesis of Amitriptyline and Related Substances. Hydroboration of 5-Allylidene-5H-dibenzo[a,d]-10,11- dihydrocycloheptene. J. Org. Chem. 1963, 28, 1751-1753.
8. Davis, M. A.; Winthrop, S. O.; Stewart, J.; Sunahara, F. A.; Herr, F. New Psychotropic Agents. V. Derivatives of 5-Cyano- and 5-Caboxamidodibenzo[a,d] cycloheptadiene. J. Med. Chem. 1963, 6, 251-255.
9. Schindler, W.; Häfliger F. Uber Derivate des Iminodibenzyls. Helv. Chim. Acta. 1954, 59, 472-483.
10. Hoffmeister, V.F.; Wutke, W.; Kroneberg G. Zur Pharmakologie des Thymolepticum Noxiptilin. Arzneimittel Forsch. 1969, 19, 846-878.
11. Hoffmeister, V.F. Zur Frage pharmakologisch-klinischer Wirkungsbeziehungen bei Antidepressiva, dargestellt am Beispiel von Noxiptilin. Arzneimittel Forsch. 1969, 19, 458-467.
12. Kairuz, T.; Truter, I.; Hugo, J.; Foxcroft, C. Prescribing patterns of tricyclic and selective serotonin reuptake inhibitor antidepressants among a sample of adolescents and young adults. Pharmacoepidem. Dr. S. 2003, 12, 379-382.
13. Barbui, C.; Guaiana, G.; Hotopl, M. Amitriptyline for inpatients and SSRIs for outpatients with depression? Systematic review and meta-regression analysis. Pharmacopsychiatry 2004, 37, 93-97.
14. Rosenbaum, T. G.; Kou, M. Are one or two dangerous? Tricyclic antidepressant exposure in toddlers. J. Emer. Med. 2005, 28, 2, 169-174.
15. Williams, J. W.; Mulrow, C. D.; Chiquette, E.; Noël, H. P.; Aguilar, C.; Cornell, J. A systematic review of newer pharmacotherapies for depression in adults: evidence report summary. Ann. Intern. Med. 2000, 132, 9, 743-756.
16. Khan, A; Khan, S.; Kolts, R.; Brown, W. A. Suicide rates in Clinical Trials of SSRIs, Other Antidepressants, and Placebo: Analysis of FDA Reports. Am. J. Psychiatry. 2003, 160, 790-792.
17. Garner, E. M.; Kelly, M. W.; Thompson, D. F. Tricyclic antidepressant withdrawal syndrome. Ann. Pharmacother. 1993, 27, 1068-1072.
18. Merkaš, S.; Litvić, M.; Mikotić-Mihun, Z.; Cepanec, I. (Belupo Ltd). Preparation of Biologically Active Derivatives of 3,7- and 1,7-Dibromodibenzosuberone. Hungarian Patent appl. HRP20000761A, 2000.
19. Oya, S.; Choi, S. R.; Hou, C.; Mu, M.; Kung, M. P.; Acton, P. D.; Siciliano, M.; Kung, H. F. 2-((2-((Dimethylamino)methyl)phenyl)thio)-5- iodophenylamine (ADAM): An Improved Serotonin Transporter Ligand. Nucl. Med. Biol. 2000, 27, 3, 249-254.
20. Baumann, P. Pharmacokinetics-Pharmacodynamics Relationships of the Selective Serotonin Reuptake Inhibitors. Clin. Pharmacokinet. 1996, 31, 6, 444-469.
21. Baumann, P. Care of Depression in the Elderly: Comparative pharmacokinetics of SSRIs. Int. Clin. Psychopharmacol. 1998, 13, S35-S43.
22. Merkaš, S.; Litvić, M.; Vinković, V.; Mikotić-Mihun, Z.; Cepanec, I. manuscript in preparation.
23. Pearson, D. E.; Keaton, O. D. Lethargic Reactions. I. The Preparation of Hindered Oximes. J. Org. Chem. 1963, 28, 1557-1558.
24. Smith, P. A. S.; Robertson, J. E. Some Factors Affecting the Site of Alkylation of Oxime Salts. J. Am. Chem. Soc. 1962, 84, 1197-1204.
25. Buehler, E. J. Alkylation of syn- and anti-Benzaldoximes. Org. Chem. 1967, 32, 261-265.
26. Grubbs, E. J.; Villarreal, J. A. Geometrical Isomerization in O-Alkyl Oximes. Tetrahedron Lett. 1969, 23, 1841-1844.
27. Holm, T. Preparation and Properties of 1,1-Diaryl-1,3-butadienes. Acta Chem. Scand. 1963, 17, 2437-2443.
28. Lešeticky, L.; Smerček, S.; Svata, V.; Podlahova, J.; Podlaha, J.; Cisarova, I. The Synthesis and X-Ray Structure of 3,7-Diiododibenzosuberone. Collect. Czech. Chem. Commun. 1990, 55, 2677-2685.
29. Ebnöther, A.; Jucker, E.; Stoll, A. Atropisomerie in der Dibenzo[a,d]cyclohepten-Reihe. Helv. Chim. Acta. 1965, 48, 1237-1249.
30. Schumacher, D. P.; Murphy, B. L.; Clark, J. E.; Tahabaz, P.; Mann, T. A. Superacid Cyclodehydration of Ketones in the Production of Tricyclic Antihistamines. J. Org. Chem. 1989, 54, 2242-2244.