New Psychotropic Agents. V. Derivatives of 5-Cyano- and 5-Carboxamidodibenzo[a,d]cycloheptadiene

Abstract

9 series of 5-dialkylaminoalkyl-5-cyano and -5-carboxamidodibenzo [a,d] cycloheptadienes has been prepared.The nitriles were derived by alkylation of 5-cyanodibenzo [a,d] cycloheptadiene; hydrolysis of some of them by sulfuric acid furnished the corresponding carboxamides. A tertiary carboxamide was prepared from pyrrolidine via dibenzo[a,d]cycloheptadiene-5-carboxylic acid and its acid chloride: this was then alkylaced in the usual manner.Certain of the compounds possessed moderate spasmolytic activity while the 5-(3-aminopropyl)-5-carbonitriles had actions on the central nervous system characteristic of the antidepressant agent amitriptyline.Various routes to the carboxylic acid were investigated.

Synthesis of Novel, Potentially Biologically Active Dibenzosuberone Derivatives

“…A wide range of compounds that contain in their structure the dibenzosuberone unit formed by two aromatic rings fused with a seven-atom cycle have been proven effective for the treatment of depressive disorders, nowadays a highly prevalent illness, as well as for a variety of painful conditions: migraine headache, noncardiac chest pain, functional dyspepsia and irritable bowel syndrome (IBS) [ 1 , 2 , 3 , 4 , 5 ]. Tricyclic antidepressants (TCAs) containing dibenzosuberone moieties mostly affect the autonomic and central nervous systems, and traditional cyclic antidepressants, like amitriptyline ( 4 ) [ 6 , 7 , 8 ], imipramine ( 5 ) [ 9 ] and noxiptiline ( 6 ) [ 10 , 11 ] continue to be used as first-line agents in treating depressive disorders and an expanding list of additional conditions [ 12 , 13 , 14 , 15 ], with amitriptyline being the most commonly prescribed TCA. …”

Thermochemistry and quantum chemical calculations of two dibenzocycloalkane nitriles

“…Information about the chemistry of nitrogen containing derivatives of dibenzocycloheptane and dibenzo-cyclooctane may be found in references [12][13][14][15][16][17][18]. Samples of both compounds were analyzed by gas chromatography and found to be over 99.9% pure.…”

Synthesis of 5H-dibenzo[a,d]cycloheptene-5-carboxylic acid and related compounds. 1,5-Hydride transfer to inductively destabilized carbonium ions

“…acid (la) and its 10,ll-dihydro derivative (2) are intermediates of considerable importance for the synthesis of compounds of potential pharmacological interest (1, 2, and references therein). l a and 2 are usually prepared by the acid-catalyzed hydrolysis of the appropriate nitriles (1-3), or by the carbonation (1-4) of some suitable organometallic reagent (usually the 5-lithio derivative).…”