Synthesis of the semi-rigid analogues of prothiadene and dithiadene as potential antidepressant and antihistamine agents: 11-[2-(Dimethylaminomethyl)cyclohexylidene]-6,11-dihydrodibenzo[b,e]thiepins and 4-[2-(dimethylaminomethyl)cyclohexylidene]-4,9-dihydrothieno-[2,3-c]-2-benzothiepins

1985 ◽  
Vol 50 (5) ◽  
pp. 1078-1088 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jan Metyš ◽  
Miroslav Protiva
Keyword(s):  
Hydrochloric Acid ◽  
Ir Spectrum ◽  
Title Compound ◽  
Dilute Hydrochloric Acid ◽  
Amino Alcohols ◽  
Geometric Isomers ◽  
Pharmacological Testing

Reaction of dibenzo[b,e]thiepin-11(6H)-one with 2-(dimethylaminomethyl)cyclohexylmagnesium chloride gave a mixture of stereoisomeric amino alcohols IX from which four homogeneous bases (IXa to IXd) were separated by chromatography. Dehydration of these compounds with boiling dilute hydrochloric acid afforded mixtures of racemic geometric isomers of the title compound VII, which were separated by crystallization. To the prevailing less polar base VIIa (E)-configuration was assigned on the basis of the IR spectrum. Using a similar procedure, thieno[2,3-c]-2-benzothiepin-4(9H)-one gave mixture of amino alcohols X from which three homogeneous stereoisomers X-A to X-C were isolated. Their dehydration resulted in both expected racemic geometric isomers VIII-A and VIII-B. Pharmacological testing proved the character of an antidepressant for the semi-rigid analogue of dithiadene VIII.

Kinetics of cyclization of S-ethoxycarbonylmethylisothiouronium chloride to 2-imino-4-thiazolidone

1979 ◽  
Vol 44 (3) ◽  
pp. 912-917 ◽  
Author(s):  
Vladimír Macháček ◽  
Said A. El-bahai ◽  
Vojeslav Štěrba
Keyword(s):  
Hydrochloric Acid ◽  
Dilute Hydrochloric Acid ◽  
Base Catalysis ◽  
General Base ◽  
Rate Limiting Step ◽  
Limiting Step ◽  
Kinetics Of Formation ◽  
Acid Catalyzed ◽  
Rate Limiting ◽  
Kinetics Of

Kinetics of formation of 2-imino-4-thiazolidone from S-ethoxycarbonylmethylisothiouronium chloride has been studied in aqueous buffers and dilute hydrochloric acid. The reaction is subject to general base catalysis, the β value being 0.65. Its rate limiting step consists in acid-catalyzed splitting off of ethoxide ion from dipolar tetrahedral intermediate. At pH < 2 formation of this intermediate becomes rate-limiting; rate constant of its formation is 2 . 104 s-1.

15N, 13C, and 1H NMR Spectra of Azo and Hydrazo Compounds Derived from 1,3,3-Trimethyl-2-methylidene-2,3-dihydroindole (Fischer Base)

1998 ◽  
Vol 63 (7) ◽  
pp. 1012-1020 ◽  
Author(s):  
Antonín Lyčka ◽  
Josef Jirman ◽  
Alois Koloničný
Keyword(s):  
Double Bond ◽  
Hydrochloric Acid ◽  
Nmr Spectra ◽  
Coupling Constants ◽  
Azo Compounds ◽  
Passive Component ◽  
Geometric Isomers ◽  
H Nmr ◽  
Fischer Base ◽  
Hydrazone Form

The 15N, 13C, and 1H NMR spectra were measured for azo and hydrazo compounds derived from 1,3,3-trimethyl-2-methylidene-2,3-dihydroindole (Fischer base), which is a passive component with a terminal methylidene group. Products prepared by coupling in hydrochloric acid exist in the corresponding hydrazone form as the E-isomers. Neutralization gives a mixture of two isomeric azo compounds which differ in the arrangement at the C(2)=C(10) double bond. This mixture was alkylated with methyl iodide to obtain the =N-N(CH3)- hydrazone derivatives. The geometric isomers were resolved based on the NOESY approach and the stereospecific behaviour of the 2J(15N,13C) coupling constants was studied for the 15N-labelled compounds.

An alternative method for assaying cerebrospinal fluid protein in the presence of methotrexate.

1988 ◽  
Vol 34 (10) ◽  
pp. 2091-2092 ◽  
Author(s):  
L M Kasper ◽  
W R Moorehead ◽  
T O Oei ◽  
M Markanich
Keyword(s):  
Cerebrospinal Fluid ◽  
Hydrochloric Acid ◽  
Trichloroacetic Acid ◽  
Dilute Hydrochloric Acid ◽  
Constant Amount ◽  
Manual Method ◽  
Turbidimetric Method ◽  
Methotrexate Concentration ◽  
Cerebrospinal Fluid Protein ◽  
Positive Interference

Abstract Therapeutic concentrations of methotrexate can cause significant positive interference in cerebrospinal fluid (CSF) protein values when assayed in the Du Pont aca. Conversely, our modified turbidimetric method, in which trichloroacetic acid (TCA) plus a sample blank containing dilute hydrochloric acid is used in place of TCA, exhibits little or no interference from methotrexate. This was verified by assaying solutions that contained a constant amount of protein (approximately 430 mg/L) and various amounts of methotrexate (0.0-2.3 x 10(-4) mol/L) by both the Du Pont aca and the manual turbidimetric method. As expected, the aca results showed increasing protein values with increasing methotrexate, whereas the manual method gave results approximating the expected protein value irrespective of the methotrexate concentration.

Antiaminic agents derived from thieno[2,3-c]-2-benzothiepin: 4-(1-Methyl-4-piperidylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin and some related compounds

1983 ◽  
Vol 48 (2) ◽  
pp. 623-641 ◽  
Author(s):  
Zdeněk Polívka ◽  
Miroslav Rajšner ◽  
Jan Metyš ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
...  
Keyword(s):  
Clinical Trials ◽  
Sulfuric Acid ◽  
Title Compound ◽  
Amino Alcohol ◽  
Hydrogen Sulfate ◽  
Geometric Isomers ◽  
Pure Alcohol ◽  
Acid Catalyzed ◽  
Anticataleptic Activity ◽  
Related Compounds

In the reaction of thieno[2,3c]-2-benzothiepin-4(9H)-one (VI) with 1-methyl-4-piperidylmagnesium chloride 7-(1-methyl-4-piperidyl)thieno[2,3-c]-2-benzothiepin-4(9H)-one (VIII) is formed in addition to the expected amino alcohol VII. The title compound I was obtained by the acid catalyzed dehydration of the pure alcohol VII. Compound I (pipethiadene) has outstanding antihistamine, antiserotonin, antireserpine and anticataleptic activity and was recommended to clinical trials as a potential antimigraine agent. For pharmacokinetic and metabolic studies there were prepared the NC2H3 analogue of pipethiadene IV and further, as potential metabolites, the demethyl analogue III, S-oxide X, demethyl S-oxide XI, N-oxide XIII and N,S-dioxide XIV. The Witting reaction of the ketone VI with 3-dimethylaminopropylidenetriphenylphosphorane resulted in a mixture of geometric isomers of 4-(3-dimethylamino-propylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin with the strongly predominating Z-isomer XVI which was isolated from the mixture by crystallization of the hydrogen maleate. The mixture with the predominating Z-isomer XVI was converted by the treatment with 80% sulfuric acid and dilution with water to a mixture with the predominating E-isomer XV (dithiadene) which was isolated by crystallization of the hydrogen sulfate. Some further new thieno[2,3-c]-2-benzothiepin derivatives were synthesized as potential intermediates.

Comparative Ganglion-blocking Potencies of the Geometric Isomers of Two Cyclic 1,2-Amino Alcohols

1959 ◽  
Vol 1 (5) ◽  
pp. 459-466 ◽  
Author(s):  
Frank G. Standaert ◽  
Seymour L. Friess ◽  
Roger O. Doty
Keyword(s):  
Amino Alcohols ◽  
Geometric Isomers

scholarly journals Acid and Enzymatic Hydrolyses of Rice Bran for Bioethanol Production

ALCHEMY ◽  
2018 ◽  
Vol 6 (1) ◽  
pp. 24
Author(s):  
Dewi Yuliani ◽  
Khoirul Achmad Julianto ◽  
Akyunul Jannah
Keyword(s):  
Enzymatic Hydrolysis ◽  
Hydrochloric Acid ◽  
Acid Hydrolysis ◽  
Sulphuric Acid ◽  
Rice Bran ◽  
Dilute Hydrochloric Acid ◽  
Cellulolytic Enzyme ◽  
Bioethanol Production ◽  
By Products ◽  
Sugar Source

<p class="BodyAbstract">Rice bran is one among many agricultural by-products containing ~50-60 wt.% of carbohydrate. The carbohydrate is a prominent sugar source for bioethanol production. The objective of this research was to study bioethanol production from rice bran by acid and enzymatic treatment. The variations of acid used were dilute hydrochloric acid and sulphuric acid, while variations of enzyme used were amylolytic and cellulolytic enzyme. Ethanol production of acid-hydrolyzed rice bran was 24.95±1.61% (v/v) by hydrochloric acid and 29.57±2.04% (v/v) by sulphuric acid. Ethanol produced by enzymatic hydrolysis was quite low i.e. 6.7±0.04%, and 8.86±0.29% (v/v) for amylolytic and cellulolytic hydrolysate, respectively.</p><p class="BodyAbstract"> </p><p>Keywords: Bioethanol, rice bran, acid hydrolysis, enzymatic hydrolysis</p>

Salts of Sulfated Oleic Acid Amides as Acid Corrosion Inhibitors

2021 ◽  
Vol 625 (3) ◽  
pp. 36-38
Author(s):  
E. K. Aminova ◽  
◽  
V. V. Fomina ◽  
Keyword(s):  
Oleic Acid ◽  
Sulfuric Acid ◽  
Hydrochloric Acid ◽  
Aqueous Solutions ◽  
Carboxylic Acids ◽  
Ammonium Salt ◽  
Dilute Hydrochloric Acid ◽  
Corrosion Inhibitors ◽  
Acid Corrosion ◽  
Protective Ability

This work is a continuation in a series of studies on the preparation of acid corrosion inhibitors based on carboxylic acids. A method of synthesis of acid corrosion inhibitors based on oleic acid amides has been developed. Several syntheses have been carried out to increase its inhibitory properties. The substances were obtained in several stages. At the first stage, amino alcohols were added to the ОA, then the resulting compounds were sulfonated with sulfuric acid. To expand the field of various inhibitors, reactions with bases are produced. As a result, salts of sulfated amides of oleic acid synthesized with amino nitrates, sulfuric acid and aqueous solutions of bases were formed. To establish the effectiveness of the compounds obtained, the protective ability in dilute hydrochloric acid was evaluated. It is established that some of the obtained substances exhibit the corresponding properties of inhibitors. In this case, the most effective is the ammonium salt of sulfated diethanolamide oleic acid.

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