π-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds

Bondžić, Bojan P.; Džambaski, Zdravko; Bondžić, Aleksandra M.; Marković, Rade

doi:10.1016/j.tet.2012.09.080

Cited by 9 publications

(12 citation statements)

References 41 publications

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Section: Introductionmentioning

confidence: 99%

“…28,29 As a result of missing X-Ray diffraction/nuclear magnetic resonance (XRD/NMR) were prepared by the regioselective N-alkylation of 2-alkylidene-4-oxothiazolidines according to the published procedure. 26,27 Desired N,N-dimethyl enamines 36 and 37 were prepared by the regioselective C-5 functionalization of 2-alkylidene-4-oxothiazolidines in a reaction with Bredereck's reagent. 5-Hydroxy thiazolidine derivatives 31 and 32 were prepared from corresponding vinyl-chlorides 31 by dimethyl sulfoxide (DMSO) initiated chloride transfer from the exocyclic C=C bond to the C(5) position of the ring and subsequent formation and hydrolysis of alkoxydimethylsulfonium salt.…”

Section: Introductionmentioning

confidence: 99%

“…They also act as folliclestimulating hormone receptor agonists and muscarinic receptor 1 agonists. 22 To find novel organic DNase I inhibitors, in the current study 41 previously synthesized thiazolidinone derivatives, including twenty-six 2-alkylidene-4-oxothiazolidines (group A, 1-26) [23][24][25][26][27] (Table 1), four 2-alkylidene-4-oxothiazolidine S-oxides (group C, 38-41) 27 (Table 3), seven 6,7-dihydro-2Hthiazolo[3,2-a]pyridin-3(5H)-ones (group D, 42-48) 26 (Table 4), two 2-alkylidene-7a-methylhexahydro-2H-pyrano [2,3-d]thiazoles (group E, 49 and 50) 26 (Table 5), and two 4a-methyl-2,3,4,4a,7,8,9,10a-octahydropyrano[2′,3′:4,5]thiazolo[3,2-a]pyridines (group F, 52 and 53) 26 (Table 6), together with 12 newly synthesized thiazolidinone derivatives, including nine 2-alkylidene-4-oxothiazolidines (group A, 27-35) (Table 1), two 2,5-dialkylidene-4-oxothiazolidines (group B, 36 and 37) (Table 2), and one 2-alkylidene-7a-methylhexahydro-2H-pyrano [2,3-d]thiazole (group E, 51) (Table 5) were evaluated for inhibitory activity against bovine pancreatic DNase I in vitro. Those inhibiting the commercial DNase I with IC 50 values below 200 µM were further evaluated for inhibitory activity against DNase I in rat liver homogenate.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Kolarević

Ilić

Kocić

et al. 2018

J of Cellular Biochemistry

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Twelve new thiazolidinones were synthesized and, together with 41 previously synthesized thiazolidinones, evaluated for inhibitory activity against deoxyribonuclease I (DNase I) in vitro. Ten compounds inhibited commercial bovine pancreatic DNase I with an IC below 200 μM and showed to be more potent DNase I inhibitors than crystal violet (IC = 365.90 ± 47.33 μM), used as a positive control. Moreover, three compounds were active against DNase I in rat liver homogenate, having an IC below 200 μM. (3-Methyl-1,4-dioxothiazolidin-2-ylidene)-N-(2-phenylethyl)ethanamide (41) exhibited the most potent DNase I inhibition against both commercial and rat liver DNase I with IC values of 115.96 ± 11.70 and 151.36 ± 15.85 μM, respectively. Site Finder and molecular docking defined the thiazolidinones interactions with the most important catalytic residues of DNase I, including the H-acceptor interaction with residues His 134 and His 252 and/or H-donor interaction with residues Glu 39 and Asp 168. The three most active compounds against both commercial and rat liver DNase I (31, 38, and 41) exhibited favorable physico-chemical, pharmacokinetic, and toxicological properties. These observations could be utilized to guide the rational design and optimization of novel thiazolidinone inhibitors. Thiazolidinones as novel DNase I inhibitors could have potential therapeutic applications due to the significant involvement of DNase I in the pathophysiology of many disease conditions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Kolarević

Ilić

Kocić

et al. 2018

J of Cellular Biochemistry

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“…An easy and efficient route has been described for the synthesis of bi‐cyclic and tri‐cyclic‐fused 4‐oxo‐thiazolidinones from the Π‐annulation reaction (Scheme ).…”

Section: Condensed 4‐thiazolidinonesmentioning

confidence: 99%

Recent Advances in Chemistry of Condensed 4‐Thiazolidinones

Gupta

2015

Journal of Heterocyclic Chem

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The syntheses of condensed 4‐thiazolidinone and its various derivatives are reviewed for the first time. Condensed 4‐thiazolidinones are important scaffolds and versatile substrates in heterocyclic chemistry, as they can be used for the synthesis of a large variety of biologically active compounds such as thiazolotriazines and as raw material for the drug synthesis. The high reactivity of active methylene group next to the carbonyl of the thiazolidin ring represents useful targets for many organic reactions.

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“…Skaja et al [39] found physical aging of the polymer network occurred concurrently with photooxidation which caused the modulus increase. Other studies by Bondzic et al [42] also highlighted tbe role of high temperature in contdbuting to coating degradation as it can increase the rate of photo-oxidation; Thompson et al [43] showed that hydrolysis can cause chain scission in polyurethane topcoat, leading inevitably to detedoration in coating properties.…”

Section: B Coating Failure Environmentmentioning

confidence: 99%

Impact of Mechanical Strain Environment on Aircraft Protective Coatings and Corrosion Protection

Tiong

Clark

2011

Journal of Aircraft

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Aircraft paint schemes (paint and sealant) are a key element of corrosion preventive measures, and ensuring that sueh schemes and other coatings are effective and durable under service conditions is essential If corrosion eosts and maintenance costs are to be minimized. Coatings can degrade under the influence (if environmental factors sueh as exposure to moisture, high temperature, ultraviolet radiation, and so forth. Coaling failure is often particularly evident at joints, and while failure may be accelerated in some regions hy local variations in coating thickness and geometry at features sueh as edges, or by erosion, it is likely that the displacements which oeeur at these locations under service loads will he a eontrihuting factor. The impact of in-serviee mechanical loading on coating degradation has so far received little attention, despite clear evidence that coatings tend to fail Hrst at specific sites sueh as sheet ends and around fastener heads. This paper argues that the magnitude of the applied service loads and the nature of the load history should be considered in predicting and assessing rates of eoating degradation, and that development of a thermomeehanieal history is a more appropriate approaeh. The likely impaet of joint displacements on the protection of aging aircraft is also discussed. Nomenclature it "( D E, e (', I. r k t '• It) ß Al* e* £/, e", fí «ihCo (Ta = crack length/depth, tntn = critical intertacial delamination length, tnm = diameter of fastener shank, mm = elastic tnodulus of coating, MPa = edge margin, mm = critical energy release of coating, i/nr = spacing between two perpendicular cracks in the coating, mm = effective length of coating, mm = critical stress intensity factor, MPa (m)''' = critical buckling stress constant = thickness of sheet, tnm = thickness of coating, mm = width of the sheet = initial postbuckling slope = geometry factor = change of effective length, mm = strain at the bottom surface of the plate = hygroscopic strain = mechanically-induced strain = strain at the top surface of the plate = thermally-induced strain = compressive residual stress, MPa = critical tensile stress, MPa = Pois.son's ratio of coating

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π-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds

Cited by 9 publications

References 41 publications

Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Synthesis and DNase I inhibitory properties of some 4‐thiazolidinone derivatives

Recent Advances in Chemistry of Condensed 4‐Thiazolidinones

Impact of Mechanical Strain Environment on Aircraft Protective Coatings and Corrosion Protection

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