Synthesis and tuberculostatic activity of derivatives of imidazole-2-thiones

Trzhtsinskaya, B. V.; Aleksandrova, A. E.; Abramova, N. D.; Andriyankova, L. V.; Виноградова, Т И; Shchegoleva, R. A.

doi:10.1007/bf00773168

Cited by 2 publications

(4 citation statements)

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“…They can be formed from a-bromoketones with substituted hydrazines and potassium thiocyanate (Lagoja et al, 2003), from a-hydroxyketones, thiourea and ammonium thiocyanate (Maduskuie et al, 1995), from benzil and thiourea (Muccioli et al, 2006), from phenylglycine methyl ester with phenyl or alkyl isothiocynate (Muccioli et al, 2006) and from diamines and CS 2 over a zinc oxide/aluminium oxide catalyst (Ballabeni et al, 1999) to name a few. The imidazole-2-thiones are extremely reactive and can be alkylated and arylated at both sulphur and nitrogen using a variety of reagents (Trzhtsinskaya and Abramova, 1991), added to activated double bonds such as 2-cyanoethene (Bagrii and Vasilenko, 1978;Trzhtsinskaya et al, 1992), acetylene (Skvortsova et al, 1974), aliphatic and alicyclic ketones and acetophenones (Hozien et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

“…The imidazole-2-thiones have also shown a wide range of biological activities, having antitumor (Iradyan et al, 1987), antiulcer (Tsuji et al, 1989), anti-inflammatory (Selig et al, 2011;Tsuji et al, 1989), antiarthritic, analgesic (Sharpe et al, 1985), antihyperthyroid (Doerge et al, 1993), tuberculostatic (Trzhtsinskaya et al, 1992), antibacterial, antifungal and insecticidal activity (Saeed and Batool, 2007). They were also shown to possess anti-HIV activity, by showing non-nucleoside reverse transcriptase inhibition (Yasser et al, 2003) and human cytosolic phospholipase A2 activity having a role in preventing inflammation (Makita et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and in vitro antiplatelet aggregation screening of novel fluorinated diethyl-2-(benzylthio)-2,3-dihydro-1H-imidazole-4,5-dicarboxylate derivatives

et al. 2014

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Seven fluorinated derivatives of diethyl-2-(benzylthio)-2,3-dihydro-1H-imidazole-4,5-dicarboxylate (a-g) as well as a nitro and chloro derivative (h-i) were prepared in five steps from glycine, ethyl formate, diethyl oxalate, potassium thiocyanate and substituted benzyl bromides. The structures of the synthesised compounds were elucidated and verified using 1 H, 13 C and 2D NMR spectroscopy where appropriate. The synthesised compounds exhibited concentration dependent antiplatelet aggregation activity on both the thrombin and ADP-induced platelet aggregation. The 4-nitro and 4-fluoro compounds exhibited the highest activity from the compounds tested, with IC 50 values of 1.06 and 1.20 mM for the thrombininduced assay and 18.57 and 12.91 mM in the ADP-induced platelet aggregation assay respectively. Three of the compounds, the 3 00 ,4 00 -difluoro (6c), 4 00 -nitro (6h) and 3 00 -chloro (6i) derivatives, have reasonable activity in both of the assays and could have potential as broad spectrum antiplatelet inhibitors. With the exception of 6c, the fluoro derivatives were not as active as the nitro and chloro compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro antiplatelet aggregation screening of novel fluorinated diethyl-2-(benzylthio)-2,3-dihydro-1H-imidazole-4,5-dicarboxylate derivatives

et al. 2014

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“…Cyclization of the latter with AcOH/HCl gave imidazo[2,1-b]thiazine 87. The reaction of compound 86 with thioglycolic acid gave thiazole derivative 88, while compound 87 can also be prepared in one-pot reaction by reacting thione with ethyl acrylate [70][71][72]. …”

Section: Addition To Activated Double Bondsmentioning

confidence: 99%

“…Dibenzoylvinyl)thio-4,5-diphenylimidazole (108) can be prepared by condensation of imidazole-2-thione 1 with dibenzoylacetylene[72]. thiazinoazoles 110 [R = Me 2 COH, EtMeCOH, BuMeCOH, 1-hydroxycyclohexyl and -cyclopentyl, Me 2 COCH(OBu)Me] were prepared in 54-98% yields by the reaction of thione 1 with cyanoacetylenes 109 in the presence of lithium hydroxide[81…”

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confidence: 99%