Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-halogeno derivatives of 10-piperazino-10,11-dihydrodibenzo[b,f]thiepins

1981 ◽  
Vol 46 (8) ◽  
pp. 1788-1799 ◽  
Author(s):  
Miroslav Protiva ◽  
Karel Šindelář ◽  
Jiřina Metyšová ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Amino Ketone ◽  
Prolonged Action ◽  
Derivatives Of ◽  
Central Depressant

Reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-fluoro and 4-bromothiophenol gave the acids IIIa and IIIc which were cyclized to 3-fluoro-8-halogenodibenzo[b,f]thiepin-10(11H)-ones IVa and IVc. The title compounds Ia and IIc were obtained via the intermediates VIac and VIIac. Reactions of (4-fluoro-2-mercaptophenyl)acetic acid or 6-fluorobenzo[b]thiophen-2(3H)-one with 4-chloronitrobenzene afforded the nitro acid IIIe which was reduced to the amino acid IIIf. Cyclization gave the amino ketone IVf which was transformed to the iodo ketone IVd. Proceeding via the intermediates VId and VIId led to the final product IId. Compounds Ia and IIcd have strong central depressant and cataleptic activity; prolongation of the effect is connected merely with the central depressant component of the action.

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.

Synthesis of amino acid derivatives of indole-3-acetic acid

2005 ◽  
Vol 2005 (10) ◽  
pp. 640-642 ◽  
Author(s):  
Ying Liu ◽  
Liang Zhao ◽  
Liang Liu ◽  
Lin-Yi Wei ◽  
Lu-Hua Lai
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
H Nmr ◽  
Derivatives Of ◽  
Indole 3 Acetic Acid

Amino acid derivatives of a modified indole-3-acetic acid have been synthesised. Fourteen new dipeptide-like compounds 3–4 were obtained and their structures were elucidated based on the IR, 1H NMR, MS spectra.

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.

Synthesis of Amino Acid Derivatives of Indole-3-acetic Acid.

ChemInform ◽  
2006 ◽  
Vol 37 (9) ◽  
Author(s):  
Ying Liu ◽  
Liang Zhao ◽  
Liang Liu ◽  
Lin-Yi Wei ◽  
Lu-Hua Lai
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Derivatives Of ◽  
Indole 3 Acetic Acid

Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-trifluoromethyl derivatives of 10-(4-methylpiperazino)- and 10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrodibenzo-[b,f]thiepin

1981 ◽  
Vol 46 (1) ◽  
pp. 118-140 ◽  
Author(s):  
Karel Šindelář ◽  
Miroslav Ryska ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiřina Metyšová ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Isolation And Characterization ◽  
Chloro Derivative ◽  
Derivatives Of ◽  
Enol Ester ◽  
Preparative Purpose ◽  
Hydroxyethyl Piperazine

A reaction of (4-fluoro-2-iodophenyl)acetic acid with 4-(trifluoromethyl)thiophenol gave the acid VIII which was cyclized with the reagent consisting from methanesulphonic acid and phosphorus pentoxide and afforded the methanesulphonic enol ester XIX. The alkaline hydrolysis resulted in 3-fluoro-8-trifluoromethyldibenzo[b,f]thiepin-10(11H)-one (XVI) which was transformed via the alcohol XXIV to the chloro derivative XXV. Substitution reactions with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine resulted in the title compounds IV and V. These products are very potent cataleptic neuroleptic agents with a prolongation of duration of the effects comparable to that of isofloxythepin and tefluthixol. A series of further synthetic experiments aimed at alternative syntheses of the acid VIII and the ketone XVI; their results were mostly not of use for preparative purpose but they led to isolation and characterization of a series of interesting heterocyclic products (XVII, XVIII, XXII, XXIII, XXIX-XXXI, XXXVI-XXXIX).

Metallkomplexe mit biologisch wichtigen Liganden, CIV [1]. ortho-Palladierte Komplexe von N,N-Dimethyl-C-phenyl-glycinmethylester. Synthese von α-Aminosäure-Derivaten durch Insertion von Isocyaniden, CO, Alkenen und Alkinen in die Pd-C-Bindung / Metal Complexes of Biologically Important Ligands, CIV [ 1]. ortho-Palladated Complexes of N,N-Dimethyl-C-phenylglycine-methylester. Synthesis of α-Amino Acid Derivatives by Insertion of Isocyanides, CO, Alkenes, and Alkynes into the Pd-C Bond

1998 ◽  
Vol 53 (4) ◽  
pp. 448-458 ◽  
Author(s):  
Andreas Böhm ◽  
Kurt Polborn ◽  
Karlheinz Sünkel ◽  
Wolfgang Beck
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Metal Complexes ◽  
Crystal Structures ◽  
Trinuclear Complex ◽  
Amino Acid Derivatives ◽  
X Ray Diffraction ◽  
X Ray ◽  
Derivatives Of ◽  
Amine Ligand

Abstract N,N-Dimethyl-C-phenylglycinemethylester reacts with Pd(OAc)2 in acetic acid to give the orthopalladated, acetato bridged complex 1. Treatment of 1 with sodium halide affords the chloro, bromo, and iodo bridged compounds [Me2NC(H)(CO2Me)C6H4PdX]2 (2a -c) (X = halide). From 2a and 1,1′-bis(diphenylphosphino)ferrocene the phosphine bridged trinuclear complex 3 is obtained. Substitution of the amine ligand of 2a by the phosphino group is observed for the reaction of 2a with Ph2PC(Me)C(Me)PPh2. Insertion of 2,6-dimethyl-phenylisocyanide, CO, alkyl-vinyl-ketones, and diphenylacetylene into the Pd-C bond o f 2a -c provides the orthosubstituted organic and organometallic derivatives of phenylglycine 6a -c, 7, 8a -b and 9a -c. The crystal structures of 1, 4a, 6a, 7 and 9a were determined by X-ray diffraction.

scholarly journals The application of ketimine derivatives of amino acids to peptide synthesis

1976 ◽  
Vol 29 (7) ◽  
pp. 1591 ◽  
Author(s):  
AP Hope ◽  
B Halpern
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Amino Acid ◽  
Biologically Active ◽  
Amino Acid Esters ◽  
Protecting Group ◽  
Active Peptides ◽  
Biologically Active Peptides ◽  
Derivatives Of ◽  
Acid Esters

N-(2-Hydroxyarylmethy1ene)amino acids have been coupled with amino acid esters to form sterically pure N-protected dipeptide esters. The protecting group can be removed by means of 80% acetic acid under conditions which leaves the t-butyloxycarbonyl protecting group intact. Biologically active peptides which are C-terminal partial sequences of substance P were prepared and were shown to have the expected vasodilator, spasmogenic and venoconstrictor properties.

Amino-Acid and Dipeptide Derivatives of 2-(6-ethyl-4-oxo-3-(4-phenyl-4H-1,2,4-triazol-3-yl)-4H-chromen-7-yloxy)acetic Acid

2005 ◽  
Vol 41 (5) ◽  
pp. 533-538 ◽  
Author(s):  
T. V. Shokol ◽  
V. V. Semenyuchenko ◽  
S. V. Shilin ◽  
A. V. Turov ◽  
A. S. Ogorodniichuk ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Derivatives Of

Amino-acid derivatives of 2-(4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yloxy)acetic acid

2012 ◽  
Vol 48 (5) ◽  
pp. 757-760
Author(s):  
M. V. Veselovskaya ◽  
S. V. Shilin ◽  
V. P. Khilya
Keyword(s):  
Acetic Acid ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Derivatives Of

Increased expression of an amino acid transporter LAT1 in healing of acetic acid-induced chronic gastric ulcer in rats

2001 ◽  
Vol 120 (5) ◽  
pp. A153-A153
Author(s):  
S MIYAMOTO ◽  
K KATO ◽  
Y ISHII ◽  
S ASAI ◽  
T NAGAISHI ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Gastric Ulcer ◽  
Amino Acid ◽  
Amino Acid Transporter ◽  
Chronic Gastric Ulcer ◽  
Acid Transporter
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