Potential metabolites of tricyclic neuroleptics: 3,7-Dimethoxy and 7,8-dimethoxy derivatives of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1981 ◽  
Vol 46 (8) ◽  
pp. 1808-1817 ◽  
Author(s):  
Miroslav Protiva ◽  
Karel Šindelář ◽  
Zdeněk Šedivý ◽  
Jiří Holubek ◽  
Marie Bartošová
Keyword(s):  
Acetic Acid ◽  
Titanium Tetrachloride ◽  
Phenyl Acetic Acid ◽  
Derivatives Of ◽  
Methoxybenzoic Acid

Reaction of 2-iodo-4-methoxybenzoic acid with 3-methoxythiophenol resulted in the acid II which was transformed via the alcohol III and the nitrile IV to [4-methoxy-2-(3-methoxyphenylthio)phenyl]acetic acid (V). Reaction of (2-iodophenyl)acetic acid with 3,4-dimethoxythiophenol gave the isomeric [2-(3,4-dimethoxyphenylthio)phenyl]acetic acid (XI). Acids V and XI afforded by cyclization the ketones VIa and VIb which were converted by reactions with 1-methylpiperazine and titanium tetrachloride to the enamines IXa and IXb. Reduction of these enamines with diborane led to the title compounds. Attempts to reduce the enamines with zinc in acetic acid resulted in hydrogenolysis, the main products being 2,3-dimethoxy- and 3,7-dimethoxy-10,11-dihydrodibenzo[b,f]thiepin (Xab).

scholarly journals Synthesis and Characterization of Ester Derivatives of Stilbene Derived from Acid Derivative (of P-Chloro Phenyl Acetic Acid, Substitute Benzaldehyde, Triethyl Amine) with Methanol and Sulphuric Acid

2015 ◽  
Vol 47 ◽  
pp. 49-55
Author(s):  
Paresh S. More ◽  
Santosh G. Singh
Keyword(s):  
Acetic Acid ◽  
Acid Derivative ◽  
Antimicrobial Activities ◽  
Second Step ◽  
Phenyl Acetic Acid ◽  
Spectral Techniques ◽  
Triethyl Amine ◽  
Stilbene Derivatives ◽  
Derivatives Of

Two stilbene derivatives have been synthesized in two step process. First step involved synthesis of acid derivative from p-chloro phenyl acetic acid, substituted benzaldehyde and triethyl amine, where as the second step involved synthesis of substituted stilbene derivatives (enoate or esters) through very simple route. These derivatives were characterized by various spectral techniques and were screened for their antimicrobial activities.

Potential metabolites of tricyclic neuroleptics: 2,8-Dihydroxy and 3,8-dihydroxy derivatives of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1979 ◽  
Vol 44 (10) ◽  
pp. 2987-2996 ◽  
Author(s):  
Miroslav Protiva ◽  
Karel Šindelář ◽  
Zdeněk Šedivý ◽  
Josef Pomykáček
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Substitution Reactions ◽  
Piperazine Derivatives ◽  
Neuroleptic Agent ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Isomeric Acid ◽  
Central Depressant ◽  
Methoxybenzoic Acid

A synthesis of the title compounds II and III, potential metabolites of the neuroleptic agent perathiepin I, was carried out. A reaction of (2-iodo-5-methoxyphenyl)acetic acid with 4-methoxythiophenol afforded the acid VI. The isomeric acid XI was obtained from 2-iodo-4-methoxybenzoic acid by reaction with 4-methoxythiophenol and via intermediates VIII-X. Both acids (VI,XI) were cyclized with polyphosphoric acid to dimethoxydibenzo[b,f]thiepin-10(11H)-onesXIIab which were transformed via the alcohols XIIIab to the chloro compounds XIVab. Substitution reactions with 1-methylpiperazine gave the piperazine derivatives IV and V and dimethoxydibenzo[b,f]thiepins XVab. The dimethoxy compounds IV and V were demethylated with boron tribromide to the diaminodiphenols II and III. The central depressant and cataleptic activity of compounds II-V is lower than that of the unsubstituted substance I.

Highly polar potential metabolites of the neuroleptic agent oxyprothepin: Synthesis of 2-hydroxy-8-methylsulfonyl and 3-hydroxy-8-methylsulfonyl derivatives of 10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin

1985 ◽  
Vol 50 (2) ◽  
pp. 519-537 ◽  
Author(s):  
Jiří Jílek ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiří Schlanger ◽  
Josef Pomykáček ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Potassium Carbonate ◽  
Neuroleptic Agent ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Methoxybenzoic Acid

The acid XI, obtained by reaction of (2-iodo-5-methoxyphenyl)acetic acid with 4-(methylsulfonyl)thiophenol (VIII) in dimethylformamide in the presence of potassium carbonate and copper, was transformed via intermediates XIIa-XIVa to compound XVa. Demethylation with boron tribromide afforded compound III, the potential metabolite of oxyprothepin (II). Its oxidation with hydrogen peroxide in acetic acid gave the sulfoxide XVII, which is a further potential metabolite. A reaction of 2-iodo-4-methoxybenzoic acid with VIII and potassium carbonate in dimethylformamide in the presence of copper afforded the acid XIX whose ester XXI was reduced with diborane to the alcohol XXII; hydrogenolysis to compound XXIII was also observed. The alcohol XXII was processed via compounds XXIV and XXV to the acid XXVI which was cyclized in a low yield to the ketone XIIb. A further processing via the intermediates XIIIb and XIVb led to compound XVb. Demethylation gave compound IV, another potential metabolite.

scholarly journals Synthesis and Characterization of some Novel Stilbene Derivatives Derived from Substituted (Phenyl Acetic Acid, Benzaldehyde, Amines) Triethyl Amine and Thionyl Chloride

2015 ◽  
Vol 43 ◽  
pp. 71-80 ◽  
Author(s):  
Paresh S. More ◽  
Santosh G. Singh
Keyword(s):  
Acetic Acid ◽  
Antimicrobial Activities ◽  
Synthesis And Characterization ◽  
Phenyl Acetic Acid ◽  
Spectral Techniques ◽  
Triethyl Amine ◽  
Stilbene Derivatives ◽  
Derivatives Of ◽  
Anti Hiv

Stilbene derivatives are widely distributed in the nature and they possess various bioactivities that includes antimicrobial, antifungal, antioxidant, hepato protective, anti-HIV, cytotoxic, anti-inflammatory and antiplatelet. We have synthesized novel derivatives of stilbenes by reacting various substituted phenyl acetic acid with aldehydes in presence of acetic anhydride and triethyl amine. These derivatives were characterised by various spectral techniques and were evaluated for their antimicrobial activities.

On-Demand Guest Release from MOF-5 Sealed with Nitrophenylacetic Acid Photocapping Groups

2019 ◽  
Author(s):  
Jingjing Yan ◽  
Rick Homan ◽  
Corrianna Boucher ◽  
Prem N. Basa ◽  
Katherine Fossum ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Crystal Violet ◽  
Dye Molecules ◽  
Phenyl Acetic Acid ◽  
On Demand ◽  
Crystal Violet Dye ◽  
Dye Diffusion ◽  
Triphenylacetic Acid

Recently, we demonstrated that triphenylacetic acid could be used to seal dye molecules within MOF-5, but guest release required digestion of the framework by treatment with acid. We prepared the sterically bulky photocapping group [bis-(3-nitro-benzyl)-amino]-(3-nitro-phenyl)-acetic acid (PC1) can prevent Crystal violet dye diffusion from inside MOF-5 until removed by photolysis.

On-Demand Guest Release from MOF-5 Sealed with Nitrophenylacetic Acid Photocapping Groups

2019 ◽  
Author(s):  
Jingjing Yan ◽  
Rick Homan ◽  
Corrianna Boucher ◽  
Prem N. Basa ◽  
Katherine Fossum ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Crystal Violet ◽  
Dye Molecules ◽  
Phenyl Acetic Acid ◽  
On Demand ◽  
Crystal Violet Dye ◽  
Dye Diffusion ◽  
Triphenylacetic Acid

Recently, we demonstrated that triphenylacetic acid could be used to seal dye molecules within MOF-5, but guest release required digestion of the framework by treatment with acid. We prepared the sterically bulky photocapping group [bis-(3-nitro-benzyl)-amino]-(3-nitro-phenyl)-acetic acid (PC1) can prevent Crystal violet dye diffusion from inside MOF-5 until removed by photolysis.

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

ChemInform Abstract: DIHALO DERIVATIVES OF NAPHTHOSTYRIL-N-ACETIC ACID

1978 ◽  
Vol 9 (34) ◽  
Author(s):  
A. P. KARISHIN ◽  
A. A. PECHKA ◽  
N. F. GRINEVA
Keyword(s):  
Acetic Acid ◽  
Derivatives Of
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