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).

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.

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

1984 ◽  
Vol 49 (11) ◽  
pp. 2638-2648 ◽  
Author(s):  
Jiří Jílek ◽  
Miroslav Rajšner ◽  
Jiřina Metyšová ◽  
Josef Pomykáček ◽  
Miroslav Protiva
Keyword(s):  
Polyphosphoric Acid ◽  
Titanium Tetrachloride ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Piperazine Derivatives ◽  
Alkyl Derivatives ◽  
Chloro Derivatives ◽  
Derivatives Of ◽  
By Products ◽  
Hydroxyethyl Piperazine

Reactions of (4-fluoro-2-iodophenyl)acetic or (2-bromo-4-fluorophenyl)acetic acid with 4-methylthiophenol, 4-ethylthiophenol and 4-isopropylthiophenol under various conditions afforded the acids IIIa-c which were cyclized with polyphosphoric acid to 8-alkyl-3-fluorodibenzo-[b,f]thiepin-10(11H)-ones IVa-c. The alcohols Va-c, which were obtained by reduction of the ketones with sodium borohydride, were transformed by treatment with hydrogen chloride to the chloro derivatives Via-c. Their substitution reactions with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine afforded the title compounds Ib, Ic and IIa. The corresponding 2-alkyl-7-fluorodibenzo[b,f]thiepins VIIa-c were obtained as by-products. Reaction of the ketone IVc with 1-methylpiperazine in the presence of titanium tetrachloride gave the enamine VIII. The piperazine derivatives prepared are very potent neuroleptic agents with regard to their acute activities. Important prolongation of the effects was found mainly with the isopropyl compounds Ic and VIII.

scholarly journals Carbohydrate binding activities of Bradyrhizobium japonicum. II. Isolation and characterization of a galactose-specific lectin.

1990 ◽  
Vol 111 (4) ◽  
pp. 1639-1643 ◽  
Author(s):  
S C Ho ◽  
M Schindler ◽  
J L Wang
Keyword(s):  
Isoelectric Focusing ◽  
Bradyrhizobium Japonicum ◽  
Affinity Column ◽  
Carbohydrate Binding ◽  
Binding Affinities ◽  
Isolation And Characterization ◽  
Relative Binding ◽  
Mannose Derivatives ◽  
Derivatives Of

Extracts of Bradyrhizobium japonicum were fractionated on Sepharose columns covalently derivatized with lactose. Elution of the material that was specifically bound to the affinity column with lactose yielded a protein of Mr approximately 38,000. Isoelectric focusing of this sample yielded two spots with pI values of 6.4 and 6.8. This protein specifically bound to galactose-containing glycoconjugates, but did not bind either to glucose or mannose. Derivatives of galactose at the C-2 position showed much weaker binding; there was an 18-fold difference in the relative binding affinities of galactose versus N-acetyl-D-galactosamine. These results indicate that we have purified a newly identified carbohydrate-binding protein from Bradyrhizobium japonicum, that can exquisitely distinguish galactose from its derivatives at the C-2 position.

scholarly journals Antihyperglycemic agents from Ammannia multiflora

2012 ◽  
Vol 7 (7) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Harish C. Upadhyay ◽  
Natasha Jaiswal ◽  
Akhilesh K. Tamrakar ◽  
Arvind K. Srivastava ◽  
Namita Gupta ◽  
...  
Keyword(s):  
Glucose Uptake ◽  
Chromatographic Separation ◽  
Antidiabetic Drug ◽  
Antihyperglycemic Activity ◽  
Chemically Modified ◽  
Isolation And Characterization ◽  
Synthetic Derivatives ◽  
Derivatives Of

The serial chromatographic separation of chloroform and n-butanol fractions of Ammannia multiflora resulted in the isolation and characterization of 4-hydroxy-α-tetralone (1) and 3,3′-(2 R,5 R)-tetrahydrofuran-2,5-diyldiphenol (ammaniol, 2). Compound 1 was chemically modified into six semi-synthetic acyl and aryl derivatives (1A - 1F). The isolated compounds 1 and 2 along with semi-synthetic derivatives 1A - 1F were evaluated for in vitro antihyperglycemic activity employing 2-deoxyglucose uptake by L-6 rat muscle cell lines. The results indicated that both the isolates, as well as derivatives (1A - 1F), have the property to stimulate glucose uptake. Ammaniol (2) increased glucose uptake significantly (64.8%), while one of the aryl derivatives of 1, 4- O-(3,4,5-trimethoxybenzoyl)-α-tetralone (1D), showed potent antihyperglycemic activity and increased glucose uptake by 94.6%, even more than rosiglitazone (88.8%). Further, since 1D possesses better antihyperglycemic activity than rosiglitazone (standard), this might be a new safer antidiabetic drug of herbal origin.

Characterization of monohydroxylated derivatives of the anticancer agent flavone-8-acetic acid by liquid chromatography with on-line UV and mass spectrometry

2007 ◽  
Vol 21 (20) ◽  
pp. 3373-3386 ◽  
Author(s):  
Minh Hien Pham ◽  
Marie-Claude Menet ◽  
Annabelle Dugay ◽  
Anne Regazzetti ◽  
Daniel Dauzonne ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Acetic Acid ◽  
Liquid Chromatography ◽  
Anticancer Agent ◽  
On Line ◽  
Derivatives Of

Isolation and Characterization of Low-indole-3-acetic Acid-producing Mutants fromBradyrhizobium elkanii

2000 ◽  
Vol 64 (7) ◽  
pp. 1359-1364 ◽  
Author(s):  
Ken YAGI ◽  
Taku MATSUMOTO ◽  
Tetsuya CHUJO ◽  
Hideaki NOJIRI ◽  
Toshio OMORI ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Isolation And Characterization ◽  
Indole 3 Acetic Acid

Isolation and characterization of culmorin derivatives produced by Fusariumculmorum CMI 14764

1992 ◽  
Vol 70 (5) ◽  
pp. 1308-1316 ◽  
Author(s):  
Gertrude C. Kasitu ◽  
John W. ApSimon ◽  
Barbara A. Blackwell ◽  
David A. Fielder ◽  
Roy Greenhalgh ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Secondary Metabolites ◽  
Liquid Culture ◽  
Farnesyl Pyrophosphate ◽  
Isolation And Characterization ◽  
Derivatives Of

Liquid culture fermentations of Fusariumculmorum yield a wide variety of secondary metabolites. In addition to known isoprenoids, such as the trichothecenes and modified trichothecenes, four new derivatives of culmorin have been isolated and characterized by spectral analysis. These compounds are 15-hydroxyculmorone (7), and 5-hydroxy- (8), 12-hydroxy- (10), and 15-hydroxyculmorin (9). The structure of culmorone is confirmed. The biosynthesis of culmorin from farnesyl pyrophosphate is substantiated through the use of 13C-acetate and the oxidation of these derivatives is discussed.

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