Neurotrope und psychotrope Substanzen XII. 2-Alkyl-9-(3-dimethylaminopropyliden)thioxanthene

Pelz, K.; Protiva, M.

doi:10.1135/cccc19672161

Cited by 8 publications

(4 citation statements)

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“…The mixture was stirred at 0°for a further 2 hr. After washing with 50 ml of 3% HC1, followed by 50 ml of 2% NaOH, the CH2CI2 solution was dried (K2CO3), filtered, and concentrated in vacuo to give 4.10 g of an amber gum: NMR (CDCI3) 7.40-7.00 (m, 7, ArH), 5.00 (m, -0.66, olefinic protons of 11 and 13), 4.48 (m, -0.66, benzylic protons of 11 and 13), 3.01 [m, -0.33, CHNfCHsh of 13], 2.45-0.75 (m, -6.5, CH2 of 9, 11, and 13), 2.15 and 2.11 [d, 6, N(CH3)2]. 18 The maleate was prepared by mixing a solution of the crude product (1.43 g, 0.…”

Section: Methodsmentioning

confidence: 99%

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Novel analogs of tricyclic psychopharmacological agents

Eichstadt¹,

Reepmeyer²,

Cook³

et al. 1976

J. Med. Chem.

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The synthesis of several novel analogs of amitriptyline and chlorprothixene, in a number of which the position of the side-chain nitrogen atom rigidly fixed with respect to the tricyclic nucleus, is described. The compounds were evaluated for antidepressant-like activity in the Dopa and serotonin interaction tests and for potential antipsychotic activity in the methamphetamine interaction test. 5-(3-Dimethylaminocyclohex-1-enyl)-5H-dibenzo[a,d]cycloheptene (12) was about equipotent with imipramine in the Dopa and methamphetamine tests, and 3-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-spiro-6'-3'-methyl-3'-azabicyclo[3.1.0]hexane (23) also displayed marked activity in the same tests. Prototype compounds for other ring systems, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene tropane (16) and 5-(3-dimethylaminocycloheptylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (18), were less active.

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Section: Methodsmentioning

confidence: 99%

“…5H-Dibenzo[a,d]cycloheptene (5). A mixture of 5/i-dibenzo [a ,d]cycloheptenone (Aldrich) (7.0 g, 0.034 mol) and Al-(¿-PrO)3 (20.0 g, 0.10 mol) was heated to 250°.…”

Section: Methodsmentioning

confidence: 99%

Novel analogs of tricyclic psychopharmacological agents

Eichstadt¹,

Reepmeyer²,

Cook³

et al. 1976

J. Med. Chem.

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“…Replacement of the piperidyl substituent of VI with an /V-methylpiperazino group also resulted in a marked decrease in potency; 7 had significantly weaker antiemetic activity than the parent. Several benzenering-substituted derivatives (11,12,16) of 7 likewise were only weakly effective in this test. The xanthen-9-ol 4 was also less active than VI.…”

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confidence: 88%

Analogs of phenothiazines. 4. Effect of structure upon neuropharmacological activity of some chlorpromazine analogs of the diphenylmethane type

Kaiser¹,

Pavloff²,

Garvey³

et al. 1972

J. Med. Chem.

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0.133 g, 10 mmoles). The soln was allowed to stand 12 hr and then poured into Et,0. The solid was collected and washed with Et,0 (230 mg, mp 188-193°), recrystd from n-PrOH, mp 213-215°(80 mg); uv (abs EtOH) max 214, 284, min 263 nyt.(Procedure D) 2,4-Diamino5-( 1-adaman tyl)-6-methylpyiiinidine ESA Salt (15b). DAMP (15a) (320 mg, 1.23 mmoles) was dissolved in abs EtOH (110 ml), C,H,SO,H (0.137 g, 1.24 mmoles) was added to this soln, the reaction mixt stirred at room temp for 0.5 hr, and the vol reduced to about 20 ml under vacuum, poured into EtjO.and refrigerated for 4 hr. After collection and washing with Et,0, the solid product (360 mg) was recrystd, PrOH (28 ml).

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“…The synthesis of the 8-methyl derivative (I, R 1 = CH 3 ) and of the 8-tert-butyl deriva tive (I, R 1 = C(CH 3 ) 3 ) (ref.l) has been described, the first of these having been found to be a four-fold more potent central depressant than chlorpromazine, the second of these being slightly weaker than chlorpromazine. At the same time, in the phenothiazine series of neuroleptics with a similarly localized substituent of alkyl type, only the ethyl derivative 2 "ethylisobutrazine" found practical application while in the thioxanthene series of 2-alkyl derivatives of prothixene the isopropyl derivative was found to be most effective here 3 . For this reason we thought it useful to extend the information on the 8-alkyl derivatives of this series and we started to work with the 8-ethyl, 8-isopropyl, 8-n-butyl and 8-n-octyl derivatives I a-I d. The study included two representatives of the series of 8-cycloalkyl derivatives, viz.…”

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confidence: 99%

8-Alkyl and 8-cycloalkyl-10-piperazinodibenzo[b,f]thiepins

Valenta¹,

Metyšová²,

Sedivy³

et al. 1974

Collect. Czech. Chem. Commun.

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Proceeding from 4-ethyl, 4-isopropyl, 4-n-butyl, 4-n-octyl , 4-cyclopropyl and 4-cyclopentyl thiophenols, the corresponding 8-substituted dibenzo [b, fl thiepin-10(11H)-ones XIV were synthesized via the intermediates IX-XIII. The ketones XIV were further converted to the 10-piperazino derivatives of the 10,1 1-dihydro series I -VI and further to enamines VII. Starting from the cyclopropyl acid IXe, the cyclopropyl analogue (XXVII) of the neuroleptic chlorprothixene was synthesized in three steps. The piperazine derivatives Ja, Ib, Ie, Ila, Jib and Vllb were found to be very effective neuroleptics with a high degree of central depressant and cataleptic activity.

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Neurotrope und psychotrope Substanzen XII. 2-Alkyl-9-(3-dimethylaminopropyliden)thioxanthene

Cited by 8 publications

References 0 publications

Novel analogs of tricyclic psychopharmacological agents

Novel analogs of tricyclic psychopharmacological agents

Analogs of phenothiazines. 4. Effect of structure upon neuropharmacological activity of some chlorpromazine analogs of the diphenylmethane type

8-Alkyl and 8-cycloalkyl-10-piperazinodibenzo[b,f]thiepins

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