scholarly journals Synthesis and Hypoglycemic Activity of the Derivatives of 4-(1,3-Thiazolidine-5-Ylidene)Pyrazole-3-Carbonic Acid and its Esters

2021 ◽  
Vol 11 (6) ◽  
pp. 14403-14412
Keyword(s):  
Carbonic Acid ◽  
Hypoglycemic Activity ◽  
Ethyl Esters ◽  
Carboxylic Group ◽  
Glucose Content ◽  
Carboxylate Groups ◽  
Entire Duration ◽  
Pharmaceutical Activity ◽  
Prolonged Effect ◽  
Derivatives Of

A preparatively convenient method for synthesizing a series of new (pyrazole-4-yl)methylenethiazolidine structures fictionalized by the carboxylate or carboxylic group in the 3rd position of the pyrazole cycle and by the oxo- thio- or imine groups in the 3rd and 5th positions of the thiazolidine ring is discussed. The method is based on the condensation of 4-formylpyrazole-3-carbonic acids and their ethyl esters with a series of substituted thiazolidines: 1,3-thiazolidine-2,4-dione, 4-thioxo-1,3-thiazolidine-2-one, 2-thioxo-1,3-thiazolidine-4-one, and 2-imino-1,3-thiazolidine-4-one. As seen from the biochemical investigations results, a clear hypoglycemic activity has been registered for the compounds mentioned in this work. Five of ten products have ensured a prolonged effect embracing the entire duration of the experiment. 1-Methyl-4[(4-oxo-2-thioxo-1,3-thiazolidine-5-iliden)methyl]-1H-pyrazole-3-carbonic acid caused the deepest decrease in the glucose content (by 2.0 mmole/L or 30.4 %), while in the case of the reference medicine pioglitazone, it was only by 1.35 mmole/L (23.9 %). Some dependence between the compound structure and its pharmaceutical activity was also found. The most prolonged and steady hypoglycemic activity was registered for (pyrazole-4-il)methylethiazolidines with methyl group as a substitute in the 1st position and carboxylic group – in the 3rd position. The additional introduction of the methyl and carboxylate groups into the pyrazole scaffold results in a prolonged and more in-depth hypoglycemic effect leading to the 1.4 times lesser drop in glucose concentration as compared to that after administration of the reference medicine.

scholarly journals Synthesis and hypoglycemic activity of derivatives of 4-((1,3-thiazolydine-5-yliden)methy)pyrazole-3-carbonic acid and its esters

2019 ◽  
pp. 37-44
Author(s):  
O. O. Perepelytsya ◽  
I. M. Yaremiy ◽  
K. P. Kupchanko ◽  
N. V. Panasenko ◽  
M. K. Bratenko ◽  
...  
Keyword(s):  
Glucose Concentration ◽  
Carbonic Acid ◽  
Preparative Method ◽  
Hypoglycemic Activity ◽  
Ethyl Esters ◽  
Control Group ◽  
Glucose Content ◽  
Standard Dosage ◽  
Carboxylate Groups ◽  
Entire Duration

An effective preparative method of synthesis of a series of new (pyrazole-4-il)methylenethiazolidine structures has been elaborated. The structures are functionalized in the 3rd position by the carboxylate or carboxyle group and in the 3rd and 5th positions of the thiazolidine cycle – by the oxo-, thio- or iminogroups. The method involves condensation of 4-formylpyrazole-3-carbonic acids and their ethyl esters with a series of the substituted thiazolidines: 1,3-thiazolidine-2,4-dione, 4-thioxo-1,3-thiazolidine-2-one, 2-thioxo-1,3-thiazolidine-4-one and 2-imino-1,3-thiazolidine-4-one. A group of 112 white adult nonlinear rats of both genders was used to investigate the hypoglycemic activity of the synthesized compounds. Pioglitazonum (5-{4-[2-(5-ethylpyridine-2-il)etoxy]benzyl}thiazolidine-2,4-dione, M=246) was used as a reference medicine in the standard dosage of 0.0214 mmole/kg. All compounds were administered intragastrically on an empty stomach using a non-traumatic catheter as a 3 % starch suspension while same dosage of the neutral suspension (without any acting medicine) was administered to the animals of the control group. Possible hypoglycemic activity of the compounds was evaluated by the changes in glucose concentration in blood measured before and 2, 4, 6, 8 and 10 hours after the single administration of a compound. An express glucometer “One Touch Select Simple” was employed for the above tests. Then all the data were processed by MS Excel. As seen from the results of the biochemical investigations, a clear hypoglycemic activity has been registered for the compounds mentioned in this work. Five of ten products have ensured a prolonged effect embracing the entire duration of the experiment. 1-methyl-4[(4-oxo-2-thiooxo-1,3-thiazolidine-5-iliden)methyl]-1H-pyrazole-3-carbonic acid caused the deepest decrease in the glucose content (2.0 units or 30.4 %) while in case of the reference medicine it was only 1.35 units (23.9 %). Some dependence between the compound structure and its pharmaceutical activity was also found. The most prolonged and steady hypoglycemic activity was registered for (pyrazole-4-il)methylethiazolidines with methyl group as a substitute in the 1st position and carboxylic group – in the 3rd position. Additional introduction of the methyl and carboxylate groups into pyrazolic scaffold results in a prolonged and deeper hypoglycemic effect leading to the 1.4 times lesser drop in glucose concentration as compared to that after administration of the reference medicine.

Synthesis and hypoglycemic activity of esterified-derivatives of mangiferin

2014 ◽  
Vol 11 (3) ◽  
pp. 296-301 ◽  
Author(s):  
Xue-Jian LI ◽  
Zheng-Cai DU ◽  
Yan HUANG ◽  
Bu-Ming LIU ◽  
Wen-Ji HU ◽  
...  
Keyword(s):  
Hypoglycemic Activity ◽  
Derivatives Of

1-Substitution derivatives of 4-aryl-2,3-dibromo-1-naphthol

1981 ◽  
Vol 46 (9) ◽  
pp. 2116-2122 ◽  
Author(s):  
Jiří Křepelka ◽  
Jiří Roubík ◽  
Jiří Holubek
Keyword(s):  
Aqueous Medium ◽  
Ethyl Esters ◽  
Derivatives Of

Alkylation of 7-ethyl-4-(4-ethylphenyl)-2,3-dibromo-1-naphthol (I) with ethyl esters of ω-bromoalkanoic acids XX-XXIII in a non-aqueous medium gave the 1-substitution derivatives II, IV, VI and VIII which were hydrolyzed to the acids III, V, VII and IX. The acid III was used for syntheses of the esters X-XIII and amides XIV-XVIII. Compounds II-XVIII exhibited moderate antineoplastic effects in animals with transplanted tumours; best results were observed with the compound II.

Preliminary Note on Dietthio and Diethylsulphone derivatives of Succinic Acid

1897 ◽  
Vol 21 ◽  
pp. 156-159
Author(s):  
Crum Brown ◽  
R. Fairbairn
Keyword(s):  
Succinic Acid ◽  
Calcium Chloride ◽  
Boiling Point ◽  
Carbonic Acid ◽  
Steam Bath ◽  
Sodium Bromide ◽  
Absolute Alcohol ◽  
Preliminary Note ◽  
Aqueous Layer ◽  
Derivatives Of

Sodium mercaptide and dibromosuccinic ether, in the proportion of two molecules of the former to one of the latter, were dissolved separately in absolute alcohol, and slowly mixed. A considerable evolution of heat took place, while sodium bromide separated out. The flask was then digested for some hours on the steam-bath. The alcohol was subsequently distilled off, and the residue, on cooling, was treated with water. An oil separated out. This oil was collected by means of a separating funnel, and the aqueous layer several times extracted with ether. The oil and the ethereal extracts were added together and dried over calcium chloride. Next morning the ether was distilled off at the ordinary pressure. The remainder was distilled in vacuo. Between 50° and 60° a few drops came over, which proved to be ethyldisulphide.The remainder came over between 150° and 170°.This latter fraction was redistilled, and a portion of it used for analysis. The boiling point at 20 mm. pressure was 160°.Combustion of dietthiosuccinic ether.Weight of substance taken = ·2477 gram.Weight of carbonic acid obtained = ·4476 gram.Weight of water obtained = ·1702 gram.

ChemInform Abstract: SYNTHESIS AND HYPOGLYCEMIC ACTIVITY OF S-ACYL DERIVATIVES OF 3-MERCAPTOPICOLINIC ACID

1977 ◽  
Vol 8 (35) ◽  
pp. no-no
Author(s):  
B. BLANK ◽  
N. W. DITULLIO ◽  
L. DEVINEY ◽  
J. T. ROBERTS ◽  
H. L. SAUNDERS
Keyword(s):  
Hypoglycemic Activity ◽  
Derivatives Of ◽  
Acyl Derivatives

Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis

1999 ◽  
Vol 54 (9) ◽  
pp. 1133-1137
Author(s):  
Astrid Knieß ◽  
Margit Gruner ◽  
Roland Mayer
Keyword(s):  
Carbonyl Group ◽  
Carbonic Acid ◽  
Ester Group ◽  
Reaction Behavior ◽  
Anthracene Derivatives ◽  
Sterical Hindrance ◽  
Derivatives Of

ß-Oxo-1 and 9-anthracenepropionate (6 and 7) reacts with DMF-acetale to enaminones 10 and 11. The reaction of 2-(dimethylamino)methylen-substituted ß-oxo-1 -anthracenepropionate (10) with hydrazines yields 5-(l-anthracenyl)-pyrazol-4-carboxylates (13). In contrast, the cyclocondensation of 3-(9-anthracenyl)-2-(dimethylamino)methylen-3-oxo-propionate (11) with hydrazine hydrochlorides gives 4-(9-anthracenoyl)-5-hydroxy-pyrazoles (14). This is caused by the sterical hindrance of the carbonyl group of the anthracene derivatives in position 9; thus, the cyclocondensation proceeds via reaction of the ester group of the enaminone 11.

Sign in / Sign up

Export Citation Format

Share Document