Synthesis of n-(4,6-dimethylpyrimidin-2-yl) hydrazinecarbothioamide
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2024-04-16 19:26
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635.655:577.112 (2)
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NEGUŢA, Andrei. Synthesis of n-(4,6-dimethylpyrimidin-2-yl) hydrazinecarbothioamide. In: Natural sciences in the dialogue of generations, 14-15 septembrie 2023, Chişinău. Chişinău: Centrul Editorial-Poligrafic al USM, 2023, p. 214. ISBN 978-9975-3430-9-1.
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Natural sciences in the dialogue of generations 2023
Conferința "Natural sciences in the dialogue of generations"
Chişinău, Moldova, 14-15 septembrie 2023

Synthesis of n-(4,6-dimethylpyrimidin-2-yl) hydrazinecarbothioamide

CZU: 635.655:577.112

Pag. 214-214

Neguţa Andrei
 
Moldova State University
 
Proiecte:
 
Disponibil în IBN: 19 octombrie 2023


Rezumat

Thiosemicarbazides are chemical compounds with the general formula R1R2NC(S)NHNH2 and are commonly used as ligands for transition metals. Many thiosemicarbazides are known where the hydrogens R1 and R2 are both substituted or only one with different radicals. The interest of science in thiosemicarbazides is that they have a vast potential for the synthesis of bioactive substances with pharmaceutical potential and are therefore widely used in the field of medicinal chemistry. They also have a wide range of diverse biological activities, such as antimicrobial, antiviral, anticancer, anti inflammatory, antitubercular, as well as topoisomerase IV and urease inhibitors. Because thiosemicarbazides can form an imine bond (-N=CH-) with carbonyl compounds, they are very often used in organic synthesis, especially to obtain thiosemicarbazones, which in turn possess a wide spectrum of medicinal properties, and are studied for their activities antibacterial, antiviral and antifungal. A very wide range of thiosemicarbazones have been clinically tested for a variety of diseases, such as tuberculosis, viral infections, malaria and cancer. Also, the complexes of thiosemicarbazones wi th metals show a wide range of biological activities. Heterocyclic pyrimidine compounds have a wide occurrence in nature as substituted derivatives, and it is known that in nucleic acids, there are three nitrogenous bases derived from pyrimidine, called pyrimidine bases: cytosine, thymine, and uracil. The pyrimidine structure, both aromatic and hydrogenated, is part of many biologically active substances and drugs, for example, barbiturates, which have hypnotic, anticonvulsant effects, and some synthetic herbicides of the sulfonylurea class. The pyrimidine core is also found as part of some vitamins, especially B1 (thiamine). To obtain N-(4,6dimethylpyrimidin-2-yl)hydrazinecarbothioamide, it was proposed to use already known synthetic routes, starting from 4,6-dimethylpyrimidin-2-amine as starting substance. It is generally known that the synthesis of thiosemicarbazides can be carried out in several ways by the reaction of hydrazides with isothiocyanates in various organic solvents. The general method involves the preparation of thiosemicarbazides by nucleophilic addition of amine or carbohydrazides to isothiocyanates. We proposed that the isothiocyanate be synthesized from this amine first using one of the three available methods, using carbon sulfide (CS2), thiophosgene (CSCl2) or disulfide tetramethylthiouram (DTMT) as intermediates.The optimization of these methods will allow us to find the most efficient way, allowing us to obtain a sufficiently pure product, with good yield to be able to be tested for biological efficiency in the future, to be subjected to condensation with a series of carbonyl components, to obtain new thiosemicarbazones that will be complexed with different metals.

Cuvinte-cheie
Thiosemicarbazides, biological activity, pyrimidine