Synthesis of 1-acyl- and 1-(thioacyl)-4-benzylpiperazines as potential antidepressants

1990 ◽  
Vol 55 (7) ◽  
pp. 1817-1827 ◽  
Author(s):  
Vojtěch Kmoníček ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Martin Valchář ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Thionyl Chloride ◽  
Antidepressant Activity ◽  
Acid Chlorides ◽  
Phosphorus Pentasulfide ◽  
Antidepressant Agent ◽  
Dimethylaminobenzoic Acid ◽  
Amino Amides

2-Nitro, 3-nitro- and 4-nitrobenzoyl chloride were reacted with 1-benzylpiperazine in benzene in the presence of triethylamine and gave the amides IV-VI, the first of which is considered a bioisostere of the antidepressant agent piberaline (I). 2-Dimethylamino-, 3-dimethylamino- and 4-dimethylaminobenzoic acid were treated with thionyl chloride in benzene in the presence of triethylamine or pyridine, and the acid chlorides formed were reacted in situ with 1-benzylpiperazine affording the amides VII-IX. The amides I and IV-VI were transformed by treatment with phosphorus pentasulfide in pyridine to the thioamides X-XIII. 4-(Dimethylaminomethyl)benzoic acid was reacted with 1-benzylpiperazine in dimethylformamide in the presence of N,N'-carbonyldiimidazole and afforded the amide XIV. Heating of ethyl 5-methylimidazole-4-carboxylate with 1-benzylpiperazine to 200-210 °C gave the amide XV together with the unexpected 1-benzyl-4-ethylpiperazine (XVI). The oily or crystalline bases of the amino amides or thioamides were mostly transformed to crystalline salts and characterized by spectra. Out of the compounds prepared only X (V⁄FB-17 070) and XIV (V⁄FB-17 114) showed indications of efficacy in tests which are considered indicative of antidepressant activity. Compounds VII, VIII, and X appeared to be mildly antidopaminergic - similarly like piberaline (I), and compounds IV, V, XI, XIV, and XV on the contrary showed signs of dopaminominetic activity.

Substituted N,N-Dimethyl-3-(phenylthio)- and -4-(phenylthio)benzylamines

1992 ◽  
Vol 57 (1) ◽  
pp. 194-203 ◽  
Author(s):  
Karel Šindelář ◽  
Vojtěch Kmoníček ◽  
Marta Hrubantová ◽  
Zdeněk Polívka
Keyword(s):  
Serotonin Receptors ◽  
Hydrobromic Acid ◽  
Antidepressant Activity ◽  
Benzoic Acids ◽  
Lithium Aluminium Hydride ◽  
Acid Chlorides ◽  
Activity Inhibition ◽  
Lithium Aluminium ◽  
The Brain

(Arylthio)benzoic acids IIa - IIe and VIb - VId were transformed via the acid chlorides to the N,N-dimethylamides which were reduced either with diborane "in situ" or with lithium aluminium hydride to N,N-dimethyl-(arylthio)benzylamines Ia - Ie and Vb - Vd. Leuckart reaction of the aldehydes IX and X with dimethylformamide and formic acid afforded directly the amines Va and Ve. Demethylation of the methoxy compounds Ia and Ve with hydrobromic acid resulted in the phenolic amines If and Vf. The most interesting N,N-dimethyl-4-(phenylthio)benzylamine (Va) hydrochloride showed affinity to cholinergic and 5-HT2 serotonin receptors in the rat brain and some properties considered indicative of antidepressant activity (inhibition of serotonin re-uptake in the brain and potentiation of yohimbine toxicity in mice).

Some 4-Substituted 1-(3-Pyridylmethyl)piperazines with Antihistamine Activity

1994 ◽  
Vol 59 (10) ◽  
pp. 2343-2350 ◽  
Author(s):  
Vojtěch Kmoníček ◽  
Martin Valchář ◽  
Zdeněk Polívka
Keyword(s):  
Acetic Acid ◽  
Nicotinic Acid ◽  
Addition Reaction ◽  
Antidepressant Activity ◽  
Structural Resemblance ◽  
Antihistamine Activity ◽  
Antidepressant Agent ◽  
Pharmacological Testing ◽  
Substituted 1

Several compounds derived from nicotinic acid were prepared within a more extensive programme aiming at the synthesis of new substances with expected antihistamine and antidepressant activity. Some of these compounds display certain structural resemblance with the antidepressant agent piberaline (EGYT 475, Trelibet®, I) and its analogues. The products were used as intermediates for the synthesis of further compounds and most of them were subjected to pharmacological testing. Substituted nicotinic acid piperazides IIa - IId and IVa - IVe were obtained by reactions of nicotinoyl chloride (prepared in situ) with the correspondingly substituted piperazines. Reduction of the piperazides IIa - IId and IVa - IVd with diborane in situ in tetrahydrofuran afforded corresponding 1-substituted 4-(3-pyridylmethyl)piperazines IIIa - IIId and Va - Vd. Whereas the alkylation of 1-(2-pyrimidinyl)piperazine with 2-(chloromethyl)pyridine in ethanol in the presence of triethylamine resulted in compounds Ve, compound Vf was obtained by the addition reaction of 1-(3-pyridylmethyl)piperazine to acrylamide. The piperazides VIe and VIf were prepared by reactions of 2-(3-pyridyl)acetic acid with 1-(2-pyrimidinyl)piperazine or 3-(1-piperazinyl)propionamide in N,N-dimethylformamide in the presence 1,1'-carbonyldiimidazole. A similar procedure starting from nicotinic acid afforded the piperazide IVf. Compounds Vc and Vd showed significant affinity for the histamine H1-receptors (inhibition of binding of 2 nmol/l [3H]mepyramine in membranes from the rat brain: Vc, IC50 = 28 nmol/l; Vd, IC50 = 148 nmol/l). They also proved active in test of histamine aerosol in guinea pigs (PD50 = 4.1 mg/kg p.o. for compound Vc and 2.4 for compound Vd). Results of a more detailed pharmacological testing of these compounds will be published elsewhere.

scholarly journals Facile Synthesis of Pd@PtM (M = Rh, Ni, Pd, Cu) Multimetallic Nanorings as Efficient Catalysts for Ethanol Oxidation Reaction

2021 ◽  
Vol 9 ◽  
Author(s):  
Xingqiao Wu ◽  
Xiao Li ◽  
Yucong Yan ◽  
Sai Luo ◽  
Jingbo Huang ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Epitaxial Growth ◽  
Oxidation Reaction ◽  
Ethanol Oxidation ◽  
Hollow Structure ◽  
Ethanol Oxidation Reaction ◽  
Hollow Nanostructures ◽  
Oxidative Etching ◽  
General Method

Pt-based multimetallic nanorings with a hollow structure are attractive as advanced catalysts due to their fantastic structure feature. However, the general method for the synthesis of such unique nanostructures is still lack. Here we report the synthesis of Pd@PtM (M = Rh, Ni, Pd, Cu) multimetallic nanorings by selective epitaxial growth of Pt alloyed shells on the periphery of Pd nanoplates in combination with oxidative etching of partial Pd in the interior. In situ generation of CO and benzoic acid arising from interfacial catalytic reactions between Pd nanoplates and benzaldehyde are critical to achieve high-quality Pt-based multimetallic nanorings. Specifically, the in-situ generated CO promotes the formation of Pt alloyed shells and their epitaxial growth on Pd nanoplates. In addition, the as-formed benzoic acid and residual oxygen are responsible for selective oxidative etching of partial Pd in the interior. When evaluated as electrocatalysts, the Pd@PtRh nanorings exhibit remarkably enhanced activity and stability for ethanol oxidation reaction (EOR) compared to the Pd@PtRh nanoplates and commercial Pt/C due to their hollow nanostructures.

Rapid In Situ Esterification Method for the Determination of Benzoic Acid in Dairy Milk by GC-FID

2014 ◽  
Vol 8 (6) ◽  
pp. 1477-1483 ◽  
Author(s):  
Sana Jawaid ◽  
Farah N. Talpur ◽  
Shafi M. Nizamani ◽  
Nusrat N. Memon ◽  
Hassan Imran Afridi ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
In Situ Esterification ◽  
Dairy Milk

scholarly journals Synthesis of Substituted 1,3-Diesters of Glycerol Using Wittig Chemistry

2014 ◽  
Vol 9 (5) ◽  
pp. 1934578X1400900
Author(s):  
Henry IC Lowe ◽  
Ngeh J. Toyang ◽  
Charah T. Watson ◽  
Joseph Bryant
Keyword(s):  
Benzoic Acid ◽  
Natural Compound ◽  
Primary Alcohol ◽  
Synthetic Approach ◽  
Triphenyl Phosphine ◽  
Phosphonium Bromide ◽  
New Compounds ◽  
First Time ◽  
Wittig Reagent

1,3-di-O-Cinnamoyl-glycerol is a natural compound isolated from a Jamaican medicinal plant commonly referred to as Ball moss (Tillandsia recurvata). The synthesis of this compound was achieved via a Wittig chemistry process. The synthetic approach started with acylation of a di-protected glycerol with cinnamoyl chloride, deprotection of the glycerol moiety, reaction of the primary alcohol with bromo acetylbromide followed by treatment with triphenyl phosphine to give the corresponding phosphonium bromide. The phosphonium bromide was then converted in situ to the Wittig reagent which is the basis for a novel route to 1,3-di-O-cinnamoyl glycerol. Four analogs were also synthesized, three of which are new and are being reported in this article for the first time. The new compounds include 3-(3,4-diemthoxy-phenyl)-acrylic acid 2-hydroxy-3-(3-ptolyl-acryloyloxy)-propyl ester (3), 2-acetoxy-5-((E)-3-(3-((E’)-3-(3,4-dimethoxyphenyl)acryloyloxy)-2-hydropropoxy)-3-oxoprop-1-enyl)benzoic acid (4) and 4-((E)-3-(3-((E)-3-(3,4-dimethoxyphenyl)acryloyloxy)-2-hydropropoxy)-3-oxoprop-1-enyl)benzoic acid (5). The compounds showed no activity in our anticancer assay.

Nanodiamond/Polyimide High Temperature Dielectric Films for Energy Storage Applications

2013 ◽  
Vol 785-786 ◽  
pp. 410-416
Author(s):  
David H. Wang ◽  
Scott P. Fillery ◽  
Michael F. Durstock ◽  
Li Ming Dai ◽  
Richard A. Vaia ◽  
...  
Keyword(s):  
Dielectric Properties ◽  
Dielectric Loss ◽  
Benzoic Acid ◽  
Surface Functionalization ◽  
High Energy ◽  
High Energy Density ◽  
Dielectric Films ◽  
Benzoic Acid Derivative ◽  
Energy Storage Applications

CP2 polyimide (prepd. from 6FDA and 1,3-bis (3-aminophenoxy) benzene) was blended with (1-50 wt.%) detonation nanodiamonds (DND, pristine, acetone-washed, and 4-(2,4,6-trimethylphenoxy) benzoic acid-functionalized), and the blends were evaluated as thin films for its potential utility in high-energy-density capacitors that would have stable dielectric properties over a wide temperature range (-55 to 300°C) and at frequencies up to or greater than 100 kHz. Both the dielectric storage and loss increased substantially with DND content. Surface functionalization (with the above benzoic acid derivative) significantly reduced the dielectric loss, while the use of acetone-washed DNDs had no effect on the dielectric loss. DND was also blended with CP2 via in-situ polymerization and found to have little effect on the dielectric properties.

On-line in-situ characterization of CO2 RESS processes for benzoic acid, cholesterol and aspirin

2007 ◽  
Vol 9 (4) ◽  
pp. 351 ◽  
Author(s):  
Jeremy J. Harrison ◽  
Changyoul Lee ◽  
Thomas Lenzer ◽  
Kawon Oum
Keyword(s):  
Benzoic Acid ◽  
In Situ Characterization ◽  
On Line
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