Recognition of arylmethylidene derivatives of imidazothiazolotriazinones as novel tubulin polymerization inhibitors.

Two series of arylmethylidene derivatives of imidazothiazolotriazinone differing in the structure of the imidazothiazolotriazine fragment were synthesized and their antiproliferative activity and effect on tubulin polymerization were evaluated. Some of the synthesized derivatives showed a significant antiproliferative effect, among which ()-7-(2,4-dichlorobenzylidene)-1,3-diethyl-1,3,4,9-tetrahydroimidazo[4,5-]thiazolo[2,3-][1,2,4]triazine-2,8(3,7)-dione 2n exhibited the highest antiproliferative activity. The GI values of the compound against 56 of the 58 cell lines were 19.

Special Issue "Development and Synthesis of Biologically Active Compounds".

The intention of this Special Issue is to focus on new achievements in the design, preparation, and in vitro and in vivo biological evaluation of bioactive molecules that can result in the development of natural or artificial potent compounds looking for promising pharmaceuticals and agrochemicals [...

Diastereoselective Synthesis of Dispiro[Imidazothiazolotriazine-Pyrrolidin-Oxindoles] and Their Isomerization Pathways in Basic Medium.

Highly diastereoselective methods for the synthesis of two series of regioisomeric polynuclear dispyroheterocyclic compounds with five or six chiral centers, comprising moieties of pyrrolidinyloxindole and imidazo[4,5-]thiazolo[3,2-]-1,2,4-triazine of linear structure or imidazo[4,5-]thiazolo[2,3-]-1,2,4-triazine of angular structure, have been developed on the basis of a [3+2] cycloaddition of azomethine ylides to functionalized imidazothiazolotriazines. Depending on the structure of the ethylenic component, cycloaddition proceeds as an process for linear derivatives, while cycloaddition to angular ones resulted in a diastereomer. Novel pathways of isomerization for the synthesized products upon treatment with sodium alkoxides have been found, which resulted in two more series of diastereomeric dispiro[imidazothiazolotriazine-pyrrolidin-oxindoles] inaccessible with the direct cycloaddition reaction.

Synthesis of imidazo[4,5-][1,3]thiazino[2,3-][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-]thiazolo[2,3-][1,2,4]triazines.

A series of imidazo[4,5-][1,3]thiazino[2,3-][1,2,4]triazines was synthesized via a cascade sequence of hydrolysis and skeletal rearrangement of imidazo[4,5-]thiazolo[2,3-][1,2,4]triazin-7(8)-ylidene)acetic acid esters in methanol upon treatment with excess KOH. Imidazo[4,5-]thiazolo[3,2-][1,2,4]triazin-6(7)-ylidene)acetic acid esters are also suitable substrates for the reaction. In this case hydrolysis and thiazole ring expansion were accompanied with the change of the thiazolotriazine junction type from thiazolo[3,2-][1,2,4]triazine to thiazino[2,3-][1,2,4]triazine.

Synthesis and Evaluation on the Fungicidal Activity of S-Alkyl Substituted Thioglycolurils.

A series of S-alkyl substituted thioglycolurils was prepared through the alkylation of corresponding thioglycolurils with halogenoalkanes and tested for their fungicidal activity against six phytopathogenic fungi from different taxonomic classes: , , , , , and and two pathogenic yeasts: and . A number of S-alkyl substituted thioglycolurils exhibited high activity against and (85-100% mycelium growth inhibition), and moderate activity against other phytopathogens. S-Ethyl substituted thioglycolurils possessed a high activity against .