Imidazothiazoles and their Hydrogenated Analogs: Methods of Synthesis and Biomedical Potential
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Imidazothiazoles and their hydrogenated analogs: methods of synthesis and biomedical potential Lesya N. Saliyeva1*, Irina V. Diachenko2, Ruslan I. Vas'kevich2, Nataliia Yu. Slyvka1, Mikhailo V. Vovk2 1
Lesya Ukrainka Volyn National University, 13 Voli Ave., Lutsk 43025, Ukraine; e-mail: [email protected] 2 Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094, Ukraine; e-mail: [email protected] Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(11), 1394–1407
Submitted June 4, 2020 Accepted July 9, 2020
The review summarizes and analyzes literature data on the methods of synthesis and biological properties of known types of imidazothiazoles. The classification of existing synthetic methods is based on the principle of the amount of research invested, from the most to the least studied. The bibliography of the review includes 80 references. Keywords: aminothiazoles, imidazothiazoles, 2-thiohydantoins, cyclization, cyclocondensation, metal-catalyzed reactions, threecomponent reactions.
Imidazothiazoles became the objects of close attention of researchers in the 1970–80s due to the ability of these structures to act as effective molecular scaffolds for synthetic, structural, and biomedical research. At present, five types of such systems are known, formed on the basis of all possible combinations of joining the thiazole and imidazole rings: imidazo[2,1-b]thiazoles I, imidazo[5,1-b]thiazoles II, imidazo[1,5-c]thiazoles III, imidazo[1,2-c]thiazoles IV, imidazo[4,5-d]thiazoles V, each with varying degrees of saturation (Fig. 1). Imidazo[2,1-b]thiazoles I are the most studied. A special interest in them was caused by the discovery among their hydrogenated derivatives of the anthelmintic drug levamisole (VI),1 which also has immunomodulatory and moderate immunosuppressive properties, the anxiolytic agent WAY-181187 (SAX-187) (VII),2 and the antineoplastic agent pifithrin-β (VIII)3 (Fig. 2). The result of the increased interest in imidazothiazole systems was the generalization of the original literature sources on the methods of synthesis and biological properties of certain types of imidazothiazoles. Thus, in 2014, a review was published4 covering the preparation of amide and urea derivatives of imidazo[2,1-b]thiazole which are inhibitors of indolamine 2,3-dioxygenase 1 (IDO1). Data on the synthesis and biological properties of aromatic imidazo[2,1-b]thiazoles was systematized and 0009-3122/20/56(11)-1394©2020 Springer Science+Business Media, LLC
Figure 1. Types of isomeric structures of imidazothiazoles I–V.
Figure 2. Structures of the anthelmintic drug levamisole (VI), the anxiolytic agent WAY-181187 (VII), and the antineoplastic agent pifithrin-β (VIII).
presented in a review published in 2015.5 A review was also published on the preparation of new imidazothiazole derivatives of chalcones and their study as potential anticancer drugs.6 Synthesis, structural modification, and biological properties of some important imidazo[5,1-b]thiazoles and imida
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