РЕАКЦИЯ ЗАМЕЩЕННЫХ БЕНЗОИЛИЗОТИОЦИАНАТОВ С МЕТИОНИНОМ И ИЗУЧЕНИЕ ПРОТИВОВОСПАЛИТЕЛЬНОЙ АКТИВНОСТИ СИНТЕЗИРОВАННЫХ СОЕДИНЕНИЙ.

Аннотация

The thiourea derivatives were synthesized by the reaction of substituted benzoyl isothiocyanates and α–amino acid – methionine in a dimethylformamide medium. The anti– inflammatory activity of the obtained compounds was studied. It has been established that N– (meta–iodobenzoyl) –NI–methionylthiourea has a much greater latitude of anti–inflammatory action and is of undoubted practical interest. Keywords. thiourea; benzoyl isothiocyanate; α-Amino acids; methionine; methionylthiourea Inflammation; anti-inflammatory activities. РЕАКЦИЯ ЗАМЕЩЕННЫХ БЕНЗОИЛИЗОТИОЦИАНАТОВ С МЕТИОНИНОМ И ИЗУЧЕНИЕ ПРОТИВОВОСПАЛИТЕЛЬНОЙ АКТИВНОСТИ СИНТЕЗИРОВАННЫХ СОЕДИНЕНИЙ. Ж.У. Абдувакилов, У.А. Балтабаев Introduction. The reaction of primary amines with isothiocyanes usually results in unsymmetrical 1,3-disubstituted thioureas. However, according to some data [1-3], the condensation of heterocyclic amines with AITC with longer heating is ambiguous: along with asymmetrically 1,3-disubstituted thioureas, symmetrically 1,3-disubstituted thioureas are formed. Symmetrical substituted thioureas, apparently, are products of secondary transformations of the formed asymmetric thioureas, the cleavage of which leads to the accumulation of two different amines and two different isothiocyanates in the mixture, then giving two symmetric thioureas: RNCS + R NH ⇄ RNHC (S) NHR ⇄ RNH + R NCS 1 2 1 2 1 R NH + R NCS → R NHC(S)NHR 1 2 1 1 1 RHN + RNCS → RNHC(S)NHR 2 The driving force behind this transformation is the difference in the basicity of the amines RNH2 and and R1NH2, on the one hand, and the reactivity of amines and aryl isothiocyanates, on the other. The ratio of the reaction products depends on the stability of the initially formed thiourea derivative. Considering that α-amino acids are non-toxic, have very interesting and diverse properties [4-6] and are, along with proteins, natural constituents of food products, we decided to carry out the synthesis of thiourea derivatives based on amino acids. For the synthesis of thiourea derivatives, prolonged heating is often required, and the product yield is usually low [7-9]. One of the main tasks of our study is the development of new methods for the preparation of thiourea derivatives based on -amino acids with a high yield of the target product while reducing the duration of the synthesis time and identifying new biological properties among them. In the literature [10], methods for obtaining substituted thioureas based on various amino acids are given. Synthesis processes involving substituted aroyl isothiocyanates with α - amino acids have not been previously studied. This determined the need to develop new reaction methods in order to obtain thiourea derivatives and to increase the yield of products, to study the patterns of such reactions, to reveal the biological activity of the synthesized compounds, in order to increase the arsenal of biologically active substances, to make judgments about the reaction mechanism for the formation of substituted thioureas. It is known that among thiourea derivatives there are physiologically active compounds that have antimicrobial, anti-tuberculosis, antiulcer and anti-inflammatory activity [11-20].