New thiopyrano[2,3-d][1,3]thiazole derivatives as potential antiviral agents

Thiazole Ring—A Biologically Active Scaffold

“…Interestingly, compound 92, the only one with an appreciated effect against influenza virus H1N1 (EC50 24 and 23 μg/mL in visual and neutral red assays, respectively), was found to be potent also against Hepatitis C virus with EC50 of 12.7 μΜ. Lesyk et al [145] synthesized twenty-four thiopyrano [2,3-d] [1,3]thiazole derivatives (Figure 37) and performed antiviral assay of a virus's panel with a protocol of the NIAID's antimicrobial acquisition [146]. According to the results of antiviral assay, some derivatives showed certain sensitivity toward influenza virus types A, H 3 N 2 , and H 5 N 1 , as well Dengue virus.…”

“…Galochkina et al [147] described the synthesis and biological evaluation of a series of novel imidazo[2,1-b] thiazole-based compounds (96a-k) as potential inhibitors of influenza virus in vitro (Figure 37). Compounds were tested against influenza virus A/Puerto Rico/8/34 (H1N1) in MDCK cells [145]. The evaluation revealed that among eleven tested compounds, only three compounds, thiophene-substituted derivatives (96i-k), exhibited activity against influenza virus with an EC 50 in the range of 13 ± 3 to 49 ± 6 µM, which is better than rimantadine (EC 50 of 72 ± 8 µM).…”

Thiopyrano[2,3-d]Thiazoles as New Efficient Scaffolds in Medicinal Chemistry

“…For example, in the reaction of crotonic acid, its amides or anhydride a mixture of rel-5R,5aR,11bS and rel-5S,5aR,11bS diastereomers (65) were formed; the isomers' ratio depends on the nature of dienophile and the reaction temperature [26]. The reaction of heterodiene 64 with maleic and fumaric acids and their derivatives (maleic anhydride, esters) passed diastereoselectively [46,47]. Moreover, independently of the stereoisomerism of the dienophile a racemic mixture of rel-(5R,5aR,11bS)-2,6-dioxo-3,5a,6,11b-tetrahydro-2H,5H-chromeno [4 ,3 :4,5] thiopyrano [2,3-d]thiazole-5-carboxylic acids derivatives 66 with a cis-Hydrogen in positions 5, 5α, and 11β of heterocyclic systems was formed.…”

“…The above-mentioned derivative had also showed micromolar ranges of cancer cell lines inhibition (GI50 = 1.95 μM) and low toxicity levels (IC50 = 23 μM), being the most active towards some lines of leukemia, non-small cell lung cancer and melanoma [40]. One more class of thiopyranothiazole derivatives being tested for antiviral activity was chromeno[4′,3′:4,5]thiopyrano [2,3-d]thiazoles 97,98 which showed inhibition activity against influenza virus type A H3N2 and H5N1 (Figure 4) [47,58] Like many other classes of synthetic small molecules, a group of 4-thiazolidinone-based derivatives was used in the search for novel selective antiviral agents [59,60]. 5,10-dihydro-2H-benzo [6,7]thiochromeno[2,3-d]thiazol-2,5,10-trione 96 possessed moderate activity against coronavirus SARS (EC 50 = 1.7 µM, SI = 14).…”

“…The above-mentioned derivative had also showed micromolar ranges of cancer cell lines inhibition (GI 50 = 1.95 µM) and low toxicity levels (IC 50 = 23 µM), being the most active towards some lines of leukemia, non-small cell lung cancer and melanoma [40]. One more class of thiopyranothiazole derivatives being tested for antiviral activity was chromeno [4 ,3 :4,5]thiopyrano [2,3-d]thiazoles 97,98 which showed inhibition activity against influenza virus type A H 3 N 2 and H 5 N 1 (Figure 4) [47,58]. 7-Aryl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano [2,3-d]thiazole-6-carbaldehydes possesed promising influence on EBV virus (compound 98, EC 50 = 0.07 µM, SI = 3279) and Hepatitis C virus (compound 99, EC 50 = 12.6 µM, SI = 43.1), respectively [31].…”