Synthesis and characterization of some new acyl-oximines derivatives

Synthesis and characterization of some new acyl-oximines derivatives

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Title: Synthesis and characterization of some new acyl-oximines derivatives
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Article_Title: Synthesis and characterization of some new acyl-oximines derivatives
Authors: Dana Mihaela Cioroianu, Laurențiu Morușciag, Miron Teodor Căproiu, Ileana Cornelia Chiriță
Affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, „Carol Davila” University of Medicine and Pharmacy, Bucharest, Romania
The Organic Chemistry Center of Romanian Academy “C.D. Nenițescu”, Bucharest, Romania
Abstract: This paper presents the synthesis of some new substances with heterocyclic structures which might become new compounds with pharmacological properties similar with the tricyclic antidepressants. These new substances are acyl-oximines derivatives with 10,11-dihydro-5H-dibenzo[a,d]-cycloheptadienic structure. A structural analysis of the synthesized compounds was performed by elemental analysis, infrared and NMR spectra, confirming the structures of these new compounds.
Keywords: 11-dihydro-5H-dibenzo[a,d]-cylcoheptene, oximes, oximines, acylation, dibenzocycloheptadienes, 5-oximino-10
References: Khan A., Leventhal R.M., Khan S.R., Brown W.A., (2002); „Severity of depression and response to antidepressants and placebo:an analysis of the Food and Drug Administration database”; Journal of Clinical Psychopharmacology 22,. 40-45;
Barbui C., Hotopf M., (2001) „Amitriptyline versus the rest: still the leading antidepressant after 40 years of randomised controlled trials”; The British Journal of Psychiatry: the Journal of Mental Science, 178 (2), 129-144;
Ernst Jucker, Ren S., Soudjin W., Wijngaarden J., Kumari M., Poyner D., Bushfield M., Hosikoski H., Fujiwara Tamenari; (2000) „Progress in Drug research”, Vol. 54, Boston, 81;
Gillman PK; (2007) „Tricyclic antidepressant pharmacology and therapeutic drug interactions update”; British Journal Pharmacology, 151(6), 737-748;
Hjak G., Rodenbeck A., Vodesholzer U et. al, (2001); „Doxepin in the treatment of primary insomnia: a placebo-controlled, double blind, polysomnographic study”, Journal of Clinical Psychiatry 62 (6), 453-463;
Cristea A. N., (2006) „Tratat de farmacologie”, Ed. Medicală, București 2006, 93-97;
Tatsumi Groshan K., Blakely R.D., Richelson E., (1997); „Pharmacological profile of antidepressants and related compounds at human monoamine transporters”; European Journal of Pharmacology 340 (2-3), 249-258;
O’Brien S.M., Scully P., Scott L.V., Dinan T.G.; (2006) „Cytokine profiles in bipolar affective disorder:focus on acutelly ill patients”; Journal of Affective Disorders, 90(2-3), 263-267;
Elenkov I.J., Iezzoni D.G., Daby A., Harris A.G., Chrousos G.P.; (2005) „Cytokine dysregulation, inflammation and well-being”, NeuroImmunoModulation, Basel, Karger AG, 12/5, 225-269;
Jones C.K., Eastwood B.J., Need A.B., Shannon H.E.; (2006) „Analgesic effects of serotonergic, noradrenergic or dual uptake inhibitors in the carrageenan test in rats: Evidence for synergism between serotonergic and noradrenergic reuptake inhibition”, Neuropharmacology, 51(7-8), 1172-1180;
Ernst Tenor, Reiner Ludwig; (1973) „Verfahven zur Herstellung von 10,11-Dihydro-5-hydroxyimino-5H-dibenzo(a,d)cyclohepta-1,4-dien”; DDR Patent 107445;
Tod W. Campbell, Ginsing R., Schmid H.; (1953) „Synthese des 2’-Acetamino-2,3,6,7-dibenzo-tropilidens und des 2-Acetamino-9,9-dimethylfluorens”, Helv.Chem.Acta 36, 1489-1499;
Morușicag L., ChirițăI., Stecoza C., Nuță D.; (2003) „The Synthesis of Tricycloheptatrienic Compounds with Potential Pharmacological Action”, Ovidius University Annals of Medical Science – Pharmacy, Vol. 1, Number 1, 134-138;
Haire Michael Joseph; (1980) „1a, 10b-Dihydrodibenzo(3,4,6,7)cyclohept(1,2-b-azirin-6(1H)-one)-oximes, process for their preparation and pharmaceutical compositions containing the antidepressant compounds among these oximes”, US Patent US4256742.
Read_full_article: pdf/22-2012/22-4-2012/SU22-4-2012-Cioroianu.pdf
Correspondence: Dana Mihaela Cioroianu, „Carol Davila” University of Medicine and Pharmacy, Bucharest, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, no. 6 Traian Vuia St., Bucharest, Romania, Phone: +40741 194439, email: dana_cioroianu@yahoo.com

Read full article
Article Title: Synthesis and characterization of some new acyl-oximines derivatives
Authors: Dana Mihaela Cioroianu, Laurențiu Morușciag, Miron Teodor Căproiu, Ileana Cornelia Chiriță
Affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, „Carol Davila” University of Medicine and Pharmacy, Bucharest, Romania
The Organic Chemistry Center of Romanian Academy “C.D. Nenițescu”, Bucharest, Romania
Abstract: This paper presents the synthesis of some new substances with heterocyclic structures which might become new compounds with pharmacological properties similar with the tricyclic antidepressants. These new substances are acyl-oximines derivatives with 10,11-dihydro-5H-dibenzo[a,d]-cycloheptadienic structure. A structural analysis of the synthesized compounds was performed by elemental analysis, infrared and NMR spectra, confirming the structures of these new compounds.
Keywords: 11-dihydro-5H-dibenzo[a,d]-cylcoheptene, oximes, oximines, acylation, dibenzocycloheptadienes, 5-oximino-10
References: Khan A., Leventhal R.M., Khan S.R., Brown W.A., (2002); „Severity of depression and response to antidepressants and placebo:an analysis of the Food and Drug Administration database”; Journal of Clinical Psychopharmacology 22,. 40-45;
Barbui C., Hotopf M., (2001) „Amitriptyline versus the rest: still the leading antidepressant after 40 years of randomised controlled trials”; The British Journal of Psychiatry: the Journal of Mental Science, 178 (2), 129-144;
Ernst Jucker, Ren S., Soudjin W., Wijngaarden J., Kumari M., Poyner D., Bushfield M., Hosikoski H., Fujiwara Tamenari; (2000) „Progress in Drug research”, Vol. 54, Boston, 81;
Gillman PK; (2007) „Tricyclic antidepressant pharmacology and therapeutic drug interactions update”; British Journal Pharmacology, 151(6), 737-748;
Hjak G., Rodenbeck A., Vodesholzer U et. al, (2001); „Doxepin in the treatment of primary insomnia: a placebo-controlled, double blind, polysomnographic study”, Journal of Clinical Psychiatry 62 (6), 453-463;
Cristea A. N., (2006) „Tratat de farmacologie”, Ed. Medicală, București 2006, 93-97;
Tatsumi Groshan K., Blakely R.D., Richelson E., (1997); „Pharmacological profile of antidepressants and related compounds at human monoamine transporters”; European Journal of Pharmacology 340 (2-3), 249-258;
O’Brien S.M., Scully P., Scott L.V., Dinan T.G.; (2006) „Cytokine profiles in bipolar affective disorder:focus on acutelly ill patients”; Journal of Affective Disorders, 90(2-3), 263-267;
Elenkov I.J., Iezzoni D.G., Daby A., Harris A.G., Chrousos G.P.; (2005) „Cytokine dysregulation, inflammation and well-being”, NeuroImmunoModulation, Basel, Karger AG, 12/5, 225-269;
Jones C.K., Eastwood B.J., Need A.B., Shannon H.E.; (2006) „Analgesic effects of serotonergic, noradrenergic or dual uptake inhibitors in the carrageenan test in rats: Evidence for synergism between serotonergic and noradrenergic reuptake inhibition”, Neuropharmacology, 51(7-8), 1172-1180;
Ernst Tenor, Reiner Ludwig; (1973) „Verfahven zur Herstellung von 10,11-Dihydro-5-hydroxyimino-5H-dibenzo(a,d)cyclohepta-1,4-dien”; DDR Patent 107445;
Tod W. Campbell, Ginsing R., Schmid H.; (1953) „Synthese des 2’-Acetamino-2,3,6,7-dibenzo-tropilidens und des 2-Acetamino-9,9-dimethylfluorens”, Helv.Chem.Acta 36, 1489-1499;
Morușicag L., ChirițăI., Stecoza C., Nuță D.; (2003) „The Synthesis of Tricycloheptatrienic Compounds with Potential Pharmacological Action”, Ovidius University Annals of Medical Science – Pharmacy, Vol. 1, Number 1, 134-138;
Haire Michael Joseph; (1980) „1a, 10b-Dihydrodibenzo(3,4,6,7)cyclohept(1,2-b-azirin-6(1H)-one)-oximes, process for their preparation and pharmaceutical compositions containing the antidepressant compounds among these oximes”, US Patent US4256742.
*Correspondence: Dana Mihaela Cioroianu, „Carol Davila” University of Medicine and Pharmacy, Bucharest, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, no. 6 Traian Vuia St., Bucharest, Romania, Phone: +40741 194439, email: dana_cioroianu@yahoo.com