scholarly journals Synthesis of malonyldi(1,2,4-triazole), the study of the kinetic and thermodynamic features of its hydrolysis and prediction of biological activity

2019 ◽  
Vol 57 (1) ◽  
pp. 41-49
Author(s):  
Pyotr P. Purygin ◽  
◽  
Maria V. Evstegneeva ◽  
Roman V. Shafigulin ◽  
Yury P. Zarubin ◽  
...  
Keyword(s):  
Biological Activity ◽  
Water System ◽  
Thermodynamic Characteristics ◽  
Heat Of Formation ◽  
Step Method ◽  
Stable Conformer ◽  
Anti Oxidant ◽  
Layer Chromatography ◽  
Kinetics Of ◽  
Hydrolysis Of

This article describes a two-step method for the synthesis of malondyl (1,2,4-triazole) (1,3-di (1H-1,2,4-triazol-1-yl)propane-1,3-dione) of 1,2,4-triazole through 1-trimethylsilyl-1,2,4-triazole, followed by reaction with malonyl chloride; the yield of the final product is 85%. The kinetics of hydrolysis of malonyldi(1,2,4-triazole) in the acetonitrile – water system (9:1) at 25 °C and 35 °C was studied, and the activation energy of the hydrolysis of malonyldi(1,2,4-triazole). To study the thermodynamic features of the reactions of obtaining this compound in the Spartan’14 1.1.4 program, a number of thermodynamic characteristics were calculated, which determine the spontaneous and exothermic nature of the process. For the molecule malonyldi(1,2,4-triazole), the most and least stable conformers were found in the program Molecular Operating Environment 2009.10, for which the surfaces of nucleophilic susceptibility were calculated in the program SCIGRESS Modeling 3.1.4. It was shown that the most stable conformer of the malonyldi(1,2,4-triazole) molecule should have the highest reactivity in reactions with different nucleophiles and the lowest value of the heat of formation. In this case, the nucleophilic susceptibility of carbonyl carbon atoms is different, despite the symmetry of the structure of the molecules malonyldi(1,2,4-triazole), which suggests a stepwise interaction of malonyldi(1,2,4-triazole) with nucleophiles. The structure of malonyldi(1,2,4-triazole) was confirmed by IR, 1H NMR spectroscopy, individuality – by thin-layer chromatography. The proposed mechanism for the hydrolysis of malonyldi(1,2,4-triazole) is described. The program PASS Professional 2007 predicted the most likely types of biological activity of the studied compounds. The most significant types of biological activity are anti-diabetic, anti-ulcer, anti-ischemic, anti-oxidant. The obtained data allow us to choose the optimal conditions for the synthesis of malonyldi(1,2,4-triazole) and to conclude that it is highly hydrolytically stable in an aqueous acetonitrile medium.

scholarly journals Synthesis, structure and reactivity of oxalyl di(4-methylimidazole)

2019 ◽  
Vol 59 (7) ◽  
pp. 122-127
Author(s):  
Pyotr P. Purygin ◽  
◽  
Alina V. Shargalo ◽  
Konstantin V. Milyutin ◽  
Yury P. Zarubin ◽  
...  
Keyword(s):  
Biological Activity ◽  
Functional Groups ◽  
1H Nmr ◽  
Chemical Shifts ◽  
Thermodynamic Characteristics ◽  
Step Method ◽  
Absorption Bands ◽  
Kinetics Of Hydrolysis ◽  
Kinetics Of ◽  
Urological Diseases

The article describes a two-step method for the synthesis of oxalyl di(4-methylimidazole) from 4(5)-methylimidazole through 1-trimethyl-4-methylimidazole followed by interaction with oxalyl chloride; the yield of the final product is 89%. The kinetics of hydrolysis, alcoholysis, and aminolysis of oxalyl di(4-methylimidazole) in acetonitrile – water (9 : 1), acetonitrile – methanol (9 : 1), acetonitrile – diethylamine (9 : 1) at 25 °C was studied. To study the thermodynamic features of the reactions to obtain this compound in the Spartan’14 1.1.4 program, a number of thermodynamic characteristics were determined that determine the spontaneous and exothermic nature of the process. The data obtained make it possible to select the optimal conditions for the synthesis of oxalyl di(4-methylimidazole) and to draw a conclusion about its low stability in media containing nucleophiles. Possible conformers were found for the oxalyl di(4-methylimidazole) molecule in the Molecular Operating Environment 2014.0901 program, for which nucleophilic susceptibility surfaces were calculated in the SCIGRESS Modeling 3.1.4 program. It was shown that the most reactive conformers in which carbonyl groups are minimally screened by fragments of 4-methylimidazole. The structure of oxalyl di(4-methylimidazole) was confirmed by IR and 1H NMR spectroscopy. Characteristic absorption bands were found in the IR spectra, confirming the presence of the corresponding functional groups in the structure of the compound, and proton signals with characteristic chemical shifts for the corresponding functional groups were detected in 1H NMR spectra. In the PASS Professional 2007 program, the most probable types of biological activity of the test compound were predicted. The most significant types of biological activity are in relation to urological diseases, antiseborrheic effect, stimulator of renal function, stimulator of leukopoiesis.

scholarly journals Synthesis of 1,1'-oxalyldibenzotriazole, study of the kinetic and thermodynamic features of its hydrolysis and prediction of biological activity

2019 ◽  
Vol 59 (7) ◽  
pp. 17-23
Author(s):  
Pyotr P. Purygin ◽  
◽  
Konstantin V. Milyutin ◽  
Yury P. Zarubin ◽  
Olga B. Grigoryeva ◽  
...  
Keyword(s):  
Biological Activity ◽  
1H Nmr Spectroscopy ◽  
Oxalyl Chloride ◽  
Thermodynamic Characteristics ◽  
Renal Diseases ◽  
Optimal Conditions ◽  
Operating Environment ◽  
Step Method ◽  
Kinetics Of Hydrolysis ◽  
Kinetics Of

The article describes a two-step method for the synthesis of 1,1'-oxalyl dibenzotriazole (bis(1H-benzotriazol-1-yl)ethane-1,2-dione) from benzotriazole via 1-trimethylsilylbenzotriazole, followed by reaction with oxalyl chloride; the yield of the final product is 87%. The kinetics of hydrolysis, alcoholysis and aminolysis of 1,1'-oxalyldibenzotriazole was studied in the systems acetonitrile – water (9 : 1), acetonitrile – methanol (9 : 1), acetonitrile – diethylamine (9 : 1) at 25 °C, and also by the equation Arrhenius values of the activation energy in the reactions of hydrolysis, alcoholysis, and aminolysis of 1,1'-oxalyl dibenzotriazole were calculated. To study the thermodynamic features of the reactions of obtaining this compound in the Spartan’14 1.1.4 program, a number of thermodynamic characteristics were calculated, determining the spontaneous and exothermic nature of the process. For the 1,1'-oxalyl dibenzotriazole molecule, possible conformers were found in the Molecular Operating Environment 2014.0901 software, for which the surfaces of nucleophilic susceptibility were calculated in the SCIGRESS Modeling 3.1.4 software. The structure of 1,1'-oxalyl dibenzotriazole was confirmed by IR and 1H NMR spectroscopy. The program PASS Professional 2007 predicted the most likely types of biological activity of the studied compounds. The most significant types of biological activity are in relation to renal diseases, anti-neurotoxic, anti-acid, anti-inflammatory. The obtained data allow us to choose the optimal conditions for the synthesis of 1,1’-oxalyl dibenzotriazole and to conclude that it is low stability in nucleophilic-containing media.

scholarly journals Isothermal and non-isothermal kinetics of hydrolysis of 1-[2-(2- pentyloxyphenylcarbamoyloxy)-(2-methoxymethyl)-ethyl]- perhydroazepinium chloride (BK 129)

2013 ◽  
Vol 60 (2) ◽  
pp. 43-48
Author(s):  
Stankovičová M. ◽  
Bezáková Ž. ◽  
Beňo P. ◽  
Húšťavová P.
Keyword(s):  
Biological Activity ◽  
Alkaline Hydrolysis ◽  
Functional Group ◽  
Isothermal Kinetics ◽  
Basic Part ◽  
Buffer Solutions ◽  
Kinetics Of Hydrolysis ◽  
Short Time ◽  
Kinetics Of ◽  
Hydrolysis Of

Abstract The substance BK 129 - 1-[2-(2-pentyloxyphenylcarbamoyloxy)-(2-methoxymethyl)-ethyl]-perhydroazepinium chloride was prepared in terms of influence of the connecting chain between the carbamate functional group and the basic part of molecule on biological activity. Such a structural feature is important with regard to its stability. In this work we determined the rate constants of alkaline hydrolysis of this compound at increased temperature under isothermal and non-isothermal conditions. The hydrolysis was also performed in buffer solutions with the purpose of evaluating its stability. Non-isothermal tests of stability enable to reduce the number of analyses. The necessary data for stability of compound are in this way achieved in a short time.

scholarly journals Kinetics of the alkaline hydrolysis of crystal violet in micelles, reverse micelles and microemulsions of cetyltrimethylammonium bromide

1970 ◽  
Vol 24 (2) ◽  
pp. 173-184 ◽  
Author(s):  
Ferdousi Begum ◽  
Md Yousuf A Molla ◽  
M Muhibur Rahman ◽  
Md Abu Bin Hasan Susan
Keyword(s):  
Crystal Violet ◽  
Alkaline Hydrolysis ◽  
Reverse Micelles ◽  
Cetyltrimethylammonium Bromide ◽  
Specific Conductivity ◽  
Water System ◽  
Chemical Society ◽  
Order Rate Constant ◽  
Kinetics Of ◽  
Hydrolysis Of

Kinetics of the alkaline hydrolysis of crystal violet (CV) in micelles, reverse micelles and microemulsions of a cationic surfactant, cetyltrimethylammonium bromide (CTAB) was studied at 25 ± 0.1 oC using spectrophotometric method. The rate of alkaline hydrolysis of CV was catalyzed by micellar solutions of CTAB. The pseudo first order rate constant (k') has been found to decrease upon incorporation of 1-butanol to cationic CTAB micelles, which displaces the substrate from the micellar into the aqueous phase. In CTAB/cyclohexane/1-butanol/water system, as the content of 1-butanol increases, specific conductivity and density of the microemulsions and reverse micelles decrease. The change in physical properties also causes change in reaction environment. A change from a micelle-rich (o/w) to a reverse micelle-rich (w/o) condition is apparent for microemulsions and consequently the k' vs. % wt. of 1-butanol profiles show an initial decrease in the k' followed by a gradual increase and finally, to a sharp increase with increasing 1-butanol content. Microemulsions and reverse micelles thus offer the potential to control rate of a reaction by formation of micelles in water phase and reverse micelles in oil phase. DOI: http://dx.doi.org/10.3329/jbcs.v24i2.9706 Journal of Bangladesh Chemical Society, Vol. 24(2), 173-184, 2011

scholarly journals Fluorescein colchicine. Synthesis, purification, and biological activity.

1978 ◽  
Vol 76 (3) ◽  
pp. 619-627 ◽  
Author(s):  
J I Clark ◽  
D Garland
Keyword(s):  
Spectral Analysis ◽  
Biological Activity ◽  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Fluorescein Isothiocyanate ◽  
Significant Loss ◽  
Colchicine Derivative ◽  
Layer Chromatography ◽  
Kinetics Of ◽  
Brain Tubulin

The synthesis of a fluorescent colchicine derivative permits the localization of colchicine-binding receptors in cells. Fluorescein colchicine (FC) was prepared by the addition of fluorescein isothiocyanate to deacetyl colchicine. The product, FC, was separated from the reactants by thin-layer chromatography (TLC). The purity of FC was demonstrated by TLC, UV spectral analysis, and analysis of the kinetics of photodecomposition. FC inhibited [3H] colchicine binding to purified brain tubulin. The biological activity of FC was compared to the activity of unlabeled colchicine on mitosis, motility, secretion, and myogenesis. The effects of FC were identical to those of unlabeled colchicine in all biological systems tested. The results demonstrate that FC may be substituted for colchicine in biological experiments without significant loss in specificity or effectiveness.

Kinetics of the acid hydrolysis of heparin from its Cu (II) complex and its relation to biological activity

Biopolymers ◽  
1973 ◽  
Vol 12 (5) ◽  
pp. 947-959 ◽  
Author(s):  
Salvatore S. Stivala ◽  
Slawko Yadlowsky ◽  
Leon Yuan
Keyword(s):  
Biological Activity ◽  
Acid Hydrolysis ◽  
Kinetics Of ◽  
Hydrolysis Of

Kinetics of alkaline hydrolysis of esters of phosphorus acids in micellar and hexagonal phases in the cetyldimethylethylammonium bromide—NaOH—water system

1998 ◽  
Vol 47 (8) ◽  
pp. 1454-1459 ◽  
Author(s):  
R. F. Bakeeva ◽  
L. A. Kudryavtseva ◽  
G. Eme ◽  
E. M. Kosacheva ◽  
V. E. Bel'skii ◽  
...  
Keyword(s):  
Alkaline Hydrolysis ◽  
Water System ◽  
Esters Of Phosphorus Acids ◽  
Hydrolysis Of Esters ◽  
Kinetics Of ◽  
Hydrolysis Of

A FACILE SYNTHESIS AND REACTIONS OF AMINO SELENOLO[2,3-b]PYRIDINE CARBOXYLATE

2015 ◽  
Vol 12 (1) ◽  
pp. 3910-3918 ◽  
Author(s):  
Dr Remon M Zaki ◽  
Prof Adel M. Kamal El-Dean ◽  
Dr Nermin A Marzouk ◽  
Prof Jehan A Micky ◽  
Mrs Rasha H Ahmed
Keyword(s):  
Biological Activity ◽  
Carbonyl Compounds ◽  
Mass Spectra ◽  
The Other ◽  
Pyridine Derivatives ◽  
Facile Synthesis ◽  
High Biological Activity ◽  
Basic Hydrolysis ◽  
Pyridine Carboxylate ◽  
Hydrolysis Of

 Incorporating selenium metal bonded to the pyridine nucleus was achieved by the reaction of selenium metal with 2-chloropyridine carbonitrile 1 in the presence of sodium borohydride as reducing agent. The resulting non isolated selanyl sodium salt was subjected to react with various α-halogenated carbonyl compounds to afford the selenyl pyridine derivatives 3a-f  which compounds 3a-d underwent Thorpe-Ziegler cyclization to give 1-amino-2-substitutedselenolo[2,3-b]pyridine compounds 4a-d, while the other compounds 3e,f failed to be cyclized. Basic hydrolysis of amino selenolo[2,3-b]pyridine carboxylate 4a followed by decarboxylation furnished the corresponding amino selenolopyridine compound 6 which was used as a versatile precursor for synthesis of other heterocyclic compound 7-16. All the newly synthesized compounds were established by elemental and spectral analysis (IR, 1H NMR) in addition to mass spectra for some of them hoping these compounds afforded high biological activity.

Influence of medium on alkaline hydrolysis of succinic acid monomethyl and monopropyl esters

1980 ◽  
Vol 45 (11) ◽  
pp. 2873-2882
Author(s):  
Vladislav Holba ◽  
Ján Benko
Keyword(s):  
Succinic Acid ◽  
Kinetic Parameters ◽  
Alkaline Hydrolysis ◽  
Specific Interactions ◽  
Nonaqueous Media ◽  
The Media ◽  
Kinetics Of ◽  
Hydrolysis Of

The kinetics of alkaline hydrolysis of succinic acid monomethyl and monopropyl esters were studied in mixed aqueous-nonaqueous media at various temperatures and ionic strengths. The results of measurements are discussed in terms of electrostatic and specific interactions between the reactants and other components of the reaction mixture. The kinetic parameters in the media under study are related to the influence of the cosolvent on the solvation sphere of the reactants.

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