Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes

The chemistry of isothiazoles is being intensively developed, which is evidenced by the wide range of selective transformations involving the isothiazole heterocycle and the high biological activity of its derivatives that can be used as effective new drugs and plant protection chemicals. Some representatives of isothiazoles have proven to be synergists of bioactive substances, which opens the way to lower the doses of drugs used and is especially important in cancer chemotherapy. In the framework of the present review, the accomplishments in the chemistry of isothiazoles over the past 18 years are examined, whilst current strategies for the synthesis of isothiazole-containing molecules and key directions of studies in this field of heterocyclic chemistry are discussed. Considerable attention is paid to chlorinated isothiazoles and strategies for their use in the synthesis of biologically active substances. In addition, a comprehensive review of existing literature in the field of metal complexes of isothiazoles is given, including the results and prospects for the practical use of isothiazole-metal complexes as catalysts for cross-coupling reactions in aqueous and aqueous-alcoholic media ('green chemistry'). 1 Introduction 2 Synthesis by Ring-Forming Reactions 2.1 Intramolecular Cyclization 2.2 (4+1)-Heterocyclization 2.3 (3+2)-Heterocyclization 2.4 Syntheses by Ring Transformations 3 Isothiazoles by Ring Functionalization Reactions: Nucleophilic Substitution, Cross-Coupling and Side-Chain Functionalization 4 Selected Syntheses of Biologically Active Isothiazole Derivatives 5 Isothiazoles in the Synthesis of Transition-Metal Complexes and in Metal-Complex Catalysis 6 Conclusion. © 2020 Georg Thieme Verlag. All rights reserved

Effective bimetallic composite catalysts for the synthesis of arylated furans and thiophenes in aqueous media

[Figure not available: see fulltext.] N-(4,6-Dimethylpyrimidin-2-yl)-5-phenylisoxazole-3-carboxamide was used as a ligand for obtaining bimetallic boron-containing heterogeneous catalysts Pd–Ni(Co)–B–L (Ni(Co):Pd = 9:1). The obtained composites were highly active as catalysts of Suzuki reaction in aqueous media, allowing to develop convenient methods for the synthesis of heterobiaryls containing furyl and thienyl rings. © 2019, Springer Science+Business Media, LLC, part of Springer Nature

НОВЫЕ ПОЛИАЗОТИСТЫЕ ЛИГАНДЫ ДЛЯ КОМПЛЕКСОВ ПАЛЛАДИЯ: СИНТЕЗ, ИСПОЛЬЗОВАНИЕ В КАТАЛИЗЕ

Approaches for the preparation of azanediyl-bisisoxazolyl (isothiazolyl) carboxamides and bis(azolyl)carboxamides - new poly-nitrogenous ligands of the chelating type - have been developed. It was shown that they are capable to form palladium complexes, interesting for research as cross-coupling reactions catalysts.Разработаны подходы к получению азанедиил-бисизоксазолил (изотиазолил)карбоксамидов и бис(азолил)карбоксамидов - новых полиазотистых лигандов хелатирующиего типа. Показано, что они способны образовывать комплексы с палладием, представляющие интерес для исследования в качестве катализаторов реакций кросс-сочетания

Quantum chemical designing of cholesterol containing radionuclide anticancer agents

In this work DFT simulation of the electron structure of cholesterol containing radionuclide agents (cluster systems of carborane (ortho-1, meta-2, para-3) and fullerenol derivatives) for oncological diseases therapy was carried out. Cluster systems of endohedral backminsterfullerenol C₆₀ derivatives have a promise perspectives in medical application as radionuclide (Fe 10a, Y 10b, Re 10c, Po 10d, Rn 10e isotope contained) nanosized anticancer agents. According to the cluster stability data obtained by the DFT calculation there is a possibility of their real practical obtainment

СИНТЕЗ 3-АМИНОМЕТИЛ-5-АРИЛИЗОКСАЗОЛОВ

An interaction between 5-aryl-3-chloromethylisoxazoles and potassium phthalimide was studied. This reaction in combination with the subsequent conversion of the obtained phthalimides into phthalazine salts and hydrolysis of the latter ones was shown to be useful for the preparation of 3-(aminomethyl)-5-arylisoxazoles in high yields.Исследовано взаимодействие 5-арил-3-хлорметилизоксазолов фталимидом калия. Показано, что эта реакция в сочетании с последующим превращением полученных фталимидов во фталазиновые соли и гидролизом последних может быть использована для получения 3-(аминометил)-5-арилизоксазолов с высокими выходами

Intramolecular Diels–Alder reaction in the synthesis of 5-arylisoxazolylmethyl- and 4,5-dichloroisothiazolylmethyl-3a,6-epoxyisoindol-3-ones

[Figure not available: see fulltext.] The reaction of 5-arylisoxazolyl- and 4,5-dichloroisothiazolylallylamines with pyromucic acid chlorides (2-furoyl and 5-methyl-2-furoyl chlorides) was studied. The reaction proceeds via the initial acylation of the allylamine nitrogen atom and the subsequent spontaneous intramolecular Diels–Alder reaction involving the furan ring of intermediate N-furoylamides with the formation of a single diastereomer of 3a,6-epoxyisoindol-3-ones. © 2021, Springer Science+Business Media, LLC, part of Springer Nature