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

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Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes SYNTHESIS0039-78811437-210X Georg Thieme Verlag Stuttgart · New York 2020, 52, 159–188 review 159 en Syn thesis A. V. Kletskov et al. Review Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes Alexey V. Kletskov*a 0000-0002-6979-545X Nikolay A. Bumaginb Fedor I. Zubkova 0000-0002-0289-0831 Dmitry G. Grudinina Vladimir I. Potkinc a Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation [email protected] b M.V. Lomonosov Moscow State University, Leninskii Gory, 1/3, Moscow 119991, Russian Federation [email protected] c Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova Str., 13, 220072, Minsk, Belarus [email protected] Received: 21.07.2019 1 Introduction Accepted after revision: 09.09.2019 Published online: 17.10.2019 DOI: 10.1055/s-0039-1690688; Art ID: ss-2019-z0406-r The search for new chemical compounds with useful License terms: properties and the development of rational ways to synthe- © 2020. The Author(s). This is an open access article published by Thieme under the size them are priority tasks in chemical science, with the terms of the Creative Commons Attribution License, permitting unrestricted use, dis- synthesis of biologically active chemical compounds for tribution and reproduction, so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/) medicine and agriculture being of particular importance. In this respect, isothiazole derivatives, which have demon- Abstract The chemistry of isothiazoles is being intensively developed, strated high potential in the design and synthesis of a wide which is evidenced by the wide range of selective transformations in- range of biologically active substances, are of great interest. volving the isothiazole heterocycle and the high biological activity of its Among natural bioregulators, isothiazole-containing com- derivatives that can be used as effective new drugs and plant protection chemicals. Some representatives of isothiazoles have proven to be syn- pounds are present in only a few examples: the phytoalex- ergists of bioactive substances, which opens the way to lower the doses ins (brassilexin1 and sinalexin),2 a prostaglandin release in- of drugs used and is especially important in cancer chemotherapy. In hibitor (pronkodin A),3 and a cytotoxin (aulosirazol).4 How- the framework of the present review, the accomplishments in the ever, this does not impede the use of the isothiazole nucleus chemistry of isothiazoles over the past 18 years are examined, whilst current strategies for the synthesis of isothiazole-containing molecules in the creation of a wide variety of bioactive substances; for and key directions of studies in this field of heterocyclic chemistry are example, compounds exhibiting anti-poliovirus activity discussed. Considerable attention is paid to chlorinated isothiazoles and have been synthesized.5 Promising compounds for the strategies for their use in the synthesis of biologically active substances. treatment of Parkinson’s disease have also been identified,6 In addition, a comprehensive review of existing literature in the field of and recently, derivatives suitable for cancer7–12 and diabe- metal complexes of isothiazoles is given, including the results and pros- 13–15 pects for the practical use of isothiazole–metal complexes as catalysts tes therapy have been obtained, as well as microbi- 16,17 for cross-coupling reactions in aqueous and aqueous–alcoholic media cides. The isothiazole heterocycle in microbicides can (‘green chemistry’). protect the molecule from the action of enzymes,18,19 there- 1 Introduction by extending the time of the molecule’s action, which in 2 Synthesis by Ring-Forming Reactions turn makes it possible to administer additional doses of the 2.1 Intramolecular Cyclization 2.2 (4+1)-Heterocyclization drug less frequently. A promising class of isothiazole-con- 2.3 (3+2)-Heterocyclization taining inhibitors of the nuclear bile acid receptor FXR has 2.4 Syntheses by Ring Transformations been found, representatives of which can be used in the 3 Isothiazoles by Ring Functionalization Reactions: Nucleophilic treatment of liver diseases.20 Some isothiazoles can be suc- Substitution, Cross-Coupling and Side-Chain Functionalization cessfully used to create competitive antagonists of insect 4 Selected Syntheses of Biologically Active Isothiazole Derivatives 21 5 Isothiazoles in the Synthesis of Transition-Metal Complexes and GABA receptors, and among the isothiazoles, effective in Metal-Complex Catalysis plant growth regulators22 and fungicides23,24 have been 6 Conclusion found. Key words heterocycles, isothiazoles, bioactive heterocycles, cataly- sis, cross-coupling, palladium, transition metals, complexes Synthesis 2020, 52, 159–188 Georg Thieme Verlag KG, Rüdigerstraße 14, 70469 Stuttgart, Germany 160 Syn thesis A. V. Kletskov et al. Review Biographical Sketches Alexey Viktorovich Kletskov Academy of Sciences of Belarus. heterocyclic chemistry, the obtained his Master’s degree He is currently a postdoctoral synthesis and study of metal from the Graduate School of the researcher at the Department complexes with substituted iso- National Academy of Sciences of Organic Chemistry at RUDN thiazoles and isoxazoles, and the of Belarus in 2013, and subse- University (Russia). His current synthesis of novel heterocyclic quently received his Ph.D. in scientific interests include the substances with high potential 2017 from the Institute of Phys- development of novel synthetic for practical applications. ical Organic Chemistry, National methodologies in the field of Nikolay Alexandrovich Prize in 1991 and earned the ti- current scientific interests are Bumagin received his Ph.D. in tle of Professor in 1992. He is focused on homo- and hetero- 1979 and his D.Sc. degree in currently Head of the Transition geneous catalysis in organic 1986 from M.V. Lomonosov Metal Catalysis Group at the De- synthesis, the chemistry of het- Moscow State University. He partment of Chemistry of Mos- erocyclic compounds, and was awarded the Nesmeyanov cow State University. His green chemistry. Fedor Ivanovich Zubkov chemistry in 2000. From 2001 His scientific interests include earned his Master’s degree in until present, he has worked as cycloaddition reactions, trans- chemistry at the Peoples’ a docent at the Organic Chemis- formations of oxygen- and ni- Friendship University of Russia try Department of the Peoples’ trogen-containing heterocycles, in 1997, followed by his Ph.D. in Friendship University of Russia. and total synthesis. Dmitry Guennadievich Gru- chemical and pharmaceutical new organic materials for elec- dinin earned his Ph.D. in chem- companies in Russia, South Ko- tronics, as well as pharmaceuti- istry at the Peoples’ Friendship rea, and Canada. His scientific cal analysis. University of Russia in 2000. interests include the synthesis Since 2001 he has worked for of heterocyclic compounds and Vladimir Ivanovich Potkin State University. In 2000 he was Chemistry, National Academy of graduated from Gorky State elected as a Corresponding Sciences of Belarus. His scientif- University (now Nizhny Member of the National Acade- ic interests include heterocyclic Novgorod, Russia) in 1975. He my of Sciences of Belarus, and in chemistry, the synthesis and received his Ph.D. in 1982 from 2009 he earned the title of Pro- study of biologically active com- the Institute of Physical Organic fessor of Chemistry. Currently, pounds, and metal complexes Chemistry of the Belorussian he is the Head of the Organic of isothiazoles and isoxazoles Academy of Sciences, and his Chemistry Department at the and their properties. D.Sc. in 1996 from Belarusian Institute of Physical Organic Synthesis 2020, 52, 159–188 161 Syn thesis A. V. Kletskov et al. Review In a few reports, isothiazoles have been studied for pos- information on metal complexes with isothiazole ligands is sible use as ligands for metal complexes. At the same time, considered in the final part of the literature review, and despite the fact that metal complexes in general have prov- will, in our opinion, provide a comprehensive picture of de- en themselves useful in creating a wide range of new tech- velopments in the field of isothiazole metal complexes, in- nologies and biologically active substances, ways to apply cluding information that has escaped the attention of other isothiazole complexes in practice have rarely been investi- authors for one reason or another. gated. Some recent publications, in which the promise of using metal complexes of isothiazole for the catalysis of or- ganic reactions and the development of pesticides has been 2 Synthesis by Ring-Forming Reactions shown,25–27 are the exception. The above facts demonstrate the high potential of using Different approaches can be used to classify the meth- isothiazole heterocycles in the design and synthesis of com- ods for producing isothiazoles, and the classification pro- pounds for different purposes and indicate broad prospects posed herein by us is based on retrosynthetic analysis. This for the further development of isothiazole chemistry, espe- allows us to build a consistent and logical understanding of cially coordination chemistry. Within the framework of the the approaches to the production of substituted isothi- present review, achievements in isothiazole chemistry over azoles, and in some cases,
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