Stereochemistry, mechanisms and applications of electrophilic reactions of organophosphorus compounds

2020 ◽  
Vol 89 (5) ◽  
pp. 537-572
Author(s):  
O I Kolodiazhnyi
Keyword(s):  
Organophosphorus Compounds ◽  
Electrophilic Reactions

ChemInform Abstract: Radical and Electrophilic Reactions of Anodic Oxidation Intermediates of Organophosphorus Compounds.

ChemInform ◽  
1990 ◽  
Vol 21 (51) ◽  
Author(s):  
A. S. ROMAKHIN ◽  
YU. A. BABKIN ◽  
F. M. PALJUTIN ◽  
V. A. ZAGUMENNOV ◽  
D. R. KHUSAINOVA ◽  
...  
Keyword(s):  
Anodic Oxidation ◽  
Organophosphorus Compounds ◽  
Electrophilic Reactions

scholarly journals Asymmetric Electrophilic Reactions in Phosphorus Chemistry

Symmetry ◽  
2020 ◽  
Vol 12 (1) ◽  
pp. 108 ◽  
Author(s):  
Anastasy O. Kolodiazhna ◽  
Oleg I. Kolodiazhnyi
Keyword(s):  
Absolute Configuration ◽  
Electrophilic Substitution ◽  
Organophosphorus Compounds ◽  
Phosphoryl Group ◽  
Substitution Reactions ◽  
Molecular Chemistry ◽  
Electrophilic Reactions ◽  
Wide Range ◽  
Further Development ◽  
Organophosphorus Chemistry

This review is devoted to the theoretic and synthetic aspects of asymmetric electrophilic substitution reactions at the stereogenic phosphorus center. The stereochemistry and mechanisms of electrophilic reactions are discussed—the substitution, addition and addition-elimination of many important reactions. The reactions of bimolecular electrophilic substitution SE2(P) proceed stereospecifically with the retention of absolute configuration at the phosphorus center, in contrast to the reactions of bimolecular nucleophilic substitution SN2(P), proceeding with inversion of absolute configuration. This conclusion was made based on stereochemical analysis of a wide range of trivalent phosphorus reactions with typical electrophiles and investigation of examples of a sizeable number of diverse compounds. The combination of stereospecific electrophilic reactions and stereoselective nucleophilic reactions is useful and promising for the further development of organophosphorus chemistry. The study of phosphoryl group transfer reactions is important for biological and molecular chemistry, as well as in studying mechanisms of chemical processes involving organophosphorus compounds. New versions of asymmetric electrophilic reactions applicable for the synthesis of enantiopure P-chiral secondary and tertiary phosphines are discussed.

Radical and Electrophilic Reactions of Anodic Oxidation Intermediates of Organophosphorus Compounds

1990 ◽  
Vol 51 (1) ◽  
pp. 194-194 ◽  
Author(s):  
A. S. Romakhin ◽  
Yu.A. Babkin ◽  
F. M. Paljutin ◽  
V. A. Zagumennov ◽  
D. R. Khusainova ◽  
...  
Keyword(s):  
Anodic Oxidation ◽  
Organophosphorus Compounds ◽  
Electrophilic Reactions

Radical and Electrophilic Reactions of Anodic Oxidation Intermediates of Organophosphorus Compounds

1990 ◽  
Vol 51 (1-4) ◽  
pp. 194-194
Author(s):  
A. S. Romakhir ◽  
Yu. A. Sabiin ◽  
F. M. Paljutin ◽  
V. A. Zagumen Nov ◽  
D. R. Rhusainova ◽  
...  
Keyword(s):  
Anodic Oxidation ◽  
Organophosphorus Compounds ◽  
Electrophilic Reactions

FEATURES OF ORGANOPHOSPHATES IMMOBILIZATION VIA STREPTAVIDIN-BIOTIN SYSTEM FOR EXPERIMENTS ON SELECTION OF APTAMERS

2020 ◽  
pp. 12-20
Author(s):  
D. A. Belinskaya ◽  
Yu. V. Chelusnova ◽  
V. V. Abzianidze ◽  
N. V. Goncharov
Keyword(s):  
Polyethylene Glycol ◽  
Organophosphorus Compounds ◽  
Binding Energies ◽  
Rna Aptamers ◽  
Main Method ◽  
Modeling Methods ◽  
Molecular Dynamics Methods ◽  
Systematic Evolution ◽  
Exponential Enrichment ◽  
Selection Of

Poisoning with organophosphorus compounds occupy one of the leading places in exotoxicosis. At the first stage, the detoxification of organophosphates can be provided with the help of DNA or RNA aptamers that bind the poison in the bloodstream. Currently, the main method of searching for aptamers is the experimental method of systematic evolution of ligands by exponential enrichment (SELEX). In the process of aptamer selection, the target molecule must be immobilized via the streptavidin-biotin complex. Since the poison molecule is small in size, to increase its availability for binding to aptamer, it is necessary to use a spacer between organophosphorus compounds and biotin. The aim of this work was to optimize the selection of aptamers for organophosphorus compounds by increasing the availability of a poison molecule immobilized via the streptavidin-biotin complex on the example of paraoxon. For this purpose, three spacers between organophosphorus compounds and biotin were tested using molecular modeling methods: three links of polyethylene glycol (3-PEG), four links of polyethylene glycol (4-PEG) and aminohexyl. The conformation of the biotinylated paraoxon complex with streptavidin and the interaction of paraoxon with the binding fragment of the aptamer were modeled using molecular docking and molecular dynamics methods. The ability of biotinylated paraoxon to bind to the aptamer has been evaluated by analyzing the surface area of the paraoxon available to the solvent, as well as by calculating the free binding energies. It has been shown that only in the case of aminohexyl immobilized paraoxon can contact the aptamer. At the final stage, the synthesis of paraoxon bound to biotin via aminohexyl was carried out.

RISK FACTORS FOR THE DEVELOPMENT OF INITIAL MANIFESTATIONS OF ATHEROGENIC CARDIOVASCULAR DISEASES IN PERSONNEL OF CHEMICALLY HAZARDOUS FACILITIES

2017 ◽  
pp. 2-7 ◽  
Author(s):  
V. A. Gorichny ◽  
D. Yu. Serdukov ◽  
A. V. Yazenok ◽  
A. V. Nosov ◽  
G. G. Zagorodnikov ◽  
...  
Keyword(s):  
Risk Factors ◽  
Statistical Analysis ◽  
Cardiovascular Diseases ◽  
Organophosphorus Compounds ◽  
Atherogenic Dyslipidemia ◽  
Chemical Weapons ◽  
Analysis Methods ◽  
High Incidence ◽  
And Control ◽  
Statistical Analysis Methods

An outpatient examination of 530 employees engaged in work with chemical weapons related to organophosphorus compounds at chemically hazardous facilities was carried out. Risk factors for the development of cardiovascular diseases of atherogenic etiology among personnel of the facilities were studied in relation to the type of work performed using statistical analysis methods. When assessing the lipidogram, a high incidence of atherogenic dyslipidemia in a group of personnel involved in the storage of chemical weapons was found out in comparison with a group of people engaged in the destruction and control of chemical weapons (73.1 vs 61.2 vs 59.6%, p

Review about structure and evaluation of reactivators of Acetylcholinesterase inhibited with neurotoxic organophosphorus compounds

2020 ◽  
Vol 27 ◽  
Author(s):  
José Daniel Figueroa-Villar ◽  
Elaine C. Petronilho ◽  
Kamil Kuca ◽  
Tanos C. C. Franca
Keyword(s):  
Organophosphorus Compounds ◽  
Chemical Warfare Agents ◽  
Nerve Impulse ◽  
Limited Capacity ◽  
New Agents ◽  
Long Time ◽  
Warfare Agents ◽  
Comprehensive Search ◽  
Pharmacology And Toxicology ◽  
The Many

Background: Neurotoxic chemical warfare agents can be classified as some of the most dangerous chemicals for humanity. The most effective of those agents are the organophosphates (OPs) capable of restricting the enzyme acetylcholinesterase (AChE), which in turn controls the nerve impulse transmission. When AChE is inhibited by OPs, its reactivation can be usually performed through cationic oximes. However, until today it has not been developed one universal defense agent, with complete effective reactivation activity for AChE inhibited by any of the many types of existing neurotoxic OPs. For this reason, before treating people intoxicated by an OP, it is necessary to determine the neurotoxic compound that was used for contamination, in order to select the most effective oxime. Unfortunately, this task usually requires a relative long time, raising the possibility of death. Cationic oximes also display a limited capacity of permeating the blood-brain barrier (BBB). This fact compromises their capacity of reactivating AChE inside the nervous system. Methods: We performed a comprehensive search on the data about OPs available on the scientific literature today in order to cover all the main drawbacks still faced in the research for the development of effective antidotes against those compounds. Results: Therefore, this review about neurotoxic OPs and the reactivation of AChE, provides insights for the new agents’ development. The most expected defense agent is a molecule without toxicity and effective to reactivate AChE inhibited by all neurotoxic OPs. Conclusion: To develop these new agents it is necessary the application of diverse scientific areas of research, especially theoretical procedures as computational science (computer simulation, docking and dynamics); organic synthesis; spectroscopic methodologies; biology, biochemical and biophysical information; medicinal chemistry, pharmacology and toxicology.

Сatalytic Phosphorylation of Aromatic C-H Bonds: from Traditional Approaches to Electrochemistry

2019 ◽  
Vol 23 (16) ◽  
pp. 1756-1770
Author(s):  
Sofia Strekalova ◽  
Mikhail Khrizanforov ◽  
Oleg Sinyashin ◽  
Yulia Budnikova
Keyword(s):  
Organophosphorus Compounds ◽  
Normal Pressure ◽  
Acid Group ◽  
Synthetic Methods ◽  
Heteroaromatic Compounds ◽  
Anti Cancer ◽  
Phosphonic Acid Group ◽  
Traditional Approaches ◽  
Anti Hiv Agents ◽  
Anti Hiv

The interest in organophosphorus compounds with a C-P bond is due to their wide use in various fields, especially in medicine and agrochemistry. Prominent examples of anti-cancer, antibacterial, and anti-HIV agents are therapeutic candidates containing a phosphonic acid group fragment. This review provides modern synthetic methods for obtaining phosphorylated aromatic and heteroaromatic compounds with the participation of complexes and salts of various metals developed in recent years as well modern protocol - electrochemical synthesis which allows carrying out reactions at room temperature and normal pressure with no additional oxidants or bases. Herein, we demonstrate new trends and evolution of phosphorylation reactions in catalysis.

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