cas 24044-52-8, 5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE

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Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives
In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a
Ghorbani, Fatemeh,Pourmousavi, Seied Ali,Kiyani, Hamzeh
p. 66 - 81
(2021/03/19)

Synthesis and anti-diabetic activity evaluation of phosphonates containing thiazolidinedione moiety
A sequence of substituted phosphonates containing the thiazolidinedione moiety was synthesized with good yields. The structures of all the synthesized compounds were confirmed by NMR (31P, 1H and 13C) and IR spectroscopy, mass spectrometry and C, H, N elemental analyses. In silico molecular docking study was also carried out to evaluate their interaction and binding modes on ligands against human PPAR γ protein for their anti-diabetic activity. From the docking results, it was determined that the compounds (Z)-dimethyl 5-(3-nitrobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7a), (Z)-dimethyl 5-(3-chloro-4-fluorobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7f), (Z)-dimethyl 5-(2,4-dichlorobenzylidene)?2,4-dioxothiazolidin-3-ylphosphonate (7e) and (Z)-dimethyl 5-((5-methoxypyridin-2-yl)methylene)?2,4-dioxothiazolidin-3-ylphosphonate (7j) have shown better binding energies (?7.8, ?7.6, ?7.5 and ?7.6 Kcal/mol) with the target gene, PPAR γ than the reference drug, Rosiglitazone (?7.4 Kcal/mol). In vitro anti-diabetic activity of the title compounds was also screened by standard α-amylase inhibition assay. Some of the tested compounds proved to possess promising activity when compared with the reference drug.
Sujatha, Bogiri,Chennamsetty, Subramanyam,Chintha, Venkataramaiah,Wudayagiri, Rajendra,Prasada Rao, Kammela
p. 586 - 591
(2020/03/23)

Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents
Thalidomide and its analogs are immunomodulatory drugs that inhibit the production of certain inflammatory mediators associated with cancer. In the present work, a new series of thalidomide analogs was designed and synthesized to obtain new effective antitumor immunomodulatory agents. The synthesized compounds were evaluated for their cytotoxic activities against a panel of four cancer cell lines (HepG-2, HCT-116, PC3 and MCF-7). Compounds 33h, 33i, 42f and 42h showed strong potencies against all tested cell lines with IC50 values ranging from 14.63 to 49.90 μM comparable to that of thalidomide (IC50 values ranging from 32.12 to 76.91 μM). The most active compounds were further evaluated for their in vitro immunomodulatory activities via estimation of human tumor necrosis factor alpha (TNF-α), human caspase-8 (CASP8), human vascular endothelial growth factor (VEGF), and nuclear factor kappa-B P65 (NF-κB P65) in HCT-116 cells. Thalidomide was used as a positive control. Compounds 33h and 42f showed a significant reduction in TNF-α. Furthermore, compounds 33i and 42f exhibited significant elevation in CASP8 levels. Compounds 33i and 42f inhibited VEGF. In addition, compound 42f showed significant decrease in levels of NF-κB p65. Moreover, apoptosis and cell cycle tests of the most active compound 42f, were performed. The results indicated that compound 42f significantly induce apoptosis in HCT-116 cells and arrest cell cycle at the G2/M phase.
El-Zahabi, Mohamed Ayman,Sakr, Helmy,El-Adl, Khaled.,Zayed, Mohamed,Abdelraheem, Adel S.,Eissa, Sally I.,Elkady, Hazem,Eissa, Ibrahim H.
(2020/09/16)

Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives
Derivatives of the thiazolidine-2,4-dione core represent a heterocyclic class with several correlated properties. In this context, the synthesis of structural analogues of these bioactive substances becomes attractive in the field of medicinal chemistry. These analogues act as antimicrobial agents against Gram-positives pathogens. The present work aimed to synthesize 10 different derivatives of 5-arylidene-thiazolidine-2,4-dione, employing urea as the catalyst in a solvent-free reaction medium, with yields that ranged from 45 to 99percent. The compounds obtained were submitted to an antimicrobial assay against S. aureus ATCC 29213. Two compounds presented minimum inhibitory concentration of 62.5 and 32.5 μg mL-1 and minimum bactericidal concentration -1, demonstrating their antibacterial potential. Principal component analysis was carried out to discriminate the compounds in active and inactive classes. Four geometric and electronic molecular descriptors were required to completely discriminate the compounds. The selected descriptors can guide us in designing new 5-arylidene-thiazolidine-2,4-dione derivatives with enhanced activity.
De Paiva, Raíssa K.C.,Da Silva, Jamerson F.,Moreira, Hudieyllen A.,Pinto, Osvaldo G.,Camargo, Lilian T.F.M.,Naves, Plínio L.F.,Camargo, Ademir J.,Ribeiro, Luciano,Ramos, Luciana M.
p. 164 - 172
(2018/12/13)

Microwave assisted urea-acetic acid catalyzed knoevenagel condensation of ethyl cyanoacetate and 1,3-Thiazolidine-2,4-dione with aromatic aldehydes under solvent free condition
Knoevengel condensation reaction of various aromatic aldehydes with ethyl cyanoacetate and 1,3-thiazolidinone-2,4-diones catalyzed by urea-acetic acid under solvent free condition where olefinic products were obtained in high yield within short reaction time.
Tryambake, Pravin. T.
p. 2401 - 2405
(2017/10/31)

Synthesis of 5-Alkylidene-2,4-thiazolidinediones and Rhodanines Promoted by Propylamino-functionalized Nano-structured SBA-15
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Veisi, Hojat,Naeimi, Alireza,Maleki, Behrooz,Ashrafi, Samaneh Sedigh,Sedrpoushan, Alireza
p. 1 - 7
(2015/07/28)

A simple, efficient and green procedure for knoevenagel condensation in hydroxy-functionalized ionic liquids
An efficient and simple Knoevenagel condensation catalyzed by hydroxy-functionalized ionic liquids proceeded smoothly in high yields under ambient and solvent-free conditions. The condensation procedures of aryl aldehydes and 2,4-thiazolidinedione was involved in hydrogen bonding interactions between the hydroxy groups of the ILs and the carbonyl group of the aldehyde. The ionic liquids can be reused for five times without significant loss in activity.
Liu, Yuting,Li, Rong,Xing, Yanjun
p. 1385 - 1397
(2015/07/15)

Synthesis and evaluation of thiazolidinedione-coumarin adducts as antidiabetic, anti-inflammatory and antioxidant agents
In the present research work, ten novel thiazolidine-2,4-dione-coumarin adducts were synthesized using three step reaction procedure. Firstly, benzylidene thiazolidinediones (II) were synthesized by facile Knoevenagel condensation reaction using various substituted aldehydes, thiourea and chloroacetic acid. Further, 3-bromoacetyl coumarins (IV) were synthesized using salicylaldehyde and ethylacetoacetate in the presence of piperidine as a catalyst forming 3-acetylcoumarin (III) which was brominated to form 3-bromoacetyl coumarin. Finally, both these compounds i.e., (II) and (IV) were condensed in the presence of dimethyl formamide and potassium carbonate leading to the formation of novel thiazolidine-2,4-dione-coumarin adducts. The synthesized compounds were screened for different biological activities. Antioxidant activity was performed in-vitro by three different methods namely FRAP (Ferric ion reducing antioxidant power) method, DPPH (1,1-diphenyl-2-picrylhydrazyl) method and hydrogen peroxide scavenging assay method using ascorbic acid as a standard. Among the synthesized compounds, FP10 and FP9 emerged as breakthrough antioxidant agents. Furthermore, the compounds were checked for their anti-inflammatory and antidiabetic activity in which compounds FP7 and FP1 showed promising anti-inflammatory and antidiabetic potential in-vivo, and may be used as lead compound for future studies.
Mishra, Garima,Sachan, Narsingh,Chawla, Pooja
p. 429 - 445
(2016/03/25)

Green synthesis of 5 arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium
An efficient synthesis of 5 arylidene-2,4-thiazolidinediones and 5-benzylidene rhodanines by the Knoevenagel condensation of 2,4- thiazolidinedione or rhodanine with aromatic aldehydes was studied. It proceeded smoothly in the presence of tetrabutylammonium hydroxide/H2O-EtOH to afford the corresponding products in high yields at 50C. Also, a series of dihydrothiophene derivatives were synthesized via the four-component reaction of aldehyde, malonitrile, 2,4-thiazolidinedione, and piperidine in the presence of Bu4NOH as a basic ionic liquid in aqueous medium. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure(Equation presented). 2013
Khazaei, Ardeshir,Veisi, Hojat,Safaei, Maryam,Ahmadian, Hossein
p. 270 - 278
(2014/04/03)

Preparation of mg-doped Ce-Zr solid catalysts and their catalytic potency for the synthesis of 5-Arylidene-2,4-thiazolidinediones via knoevenagel condensation
A series of Mg-doped Ce-Zr mixed oxides with different molar ratios were prepared by a simple co-precipitation method. The surface characterization of these materials were investigated by means of XRD, FT-IR, SEM-EDS, CO 2-TPD and BET technique
Rathod, Sandip,Navgire, Madhukar,Arbad, Balasaheb,Lande, MacHhindra
p. 196 - 201
(2012/11/13)

Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.
Shah, Sakshi,Singh, Baldev
experimental part
p. 5388 - 5391
(2012/09/22)

Ternary condensation of Biginelli thiones, chloroacetic acid, and aldehydes as an effective approach towards thiazolo[3,2-a] pyrimidines and 5-arylidenethiazolidine-2,4-diones
(Chemical Equation Presented) At the process of ethyl 6-methyl-4-aryl-2- thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates condensation with aryl aldehydes and chloroacetic acid the unexpected formation of 5- arylidenethiazolidine-2,4-diones was determined in high yields as the reaction time was increased to 20 h. The latter represent the products of destructive hydrolyzes of ethyl 2-benzylidene-7-methyl-3-oxo-5-aryl-2,3-dihydro-5H-[1,3] thiazolo[3,2-a]pyrimidine-6-carboxylates which have been proved by independent synthesis.
Lebedyeva, Iryna O.,Povstyanoy, Mykhaylo V.,Ryabitskii, Aleksey B.,Povstyanoy, Vyacheslav M.
experimental part
p. 368 - 372
(2010/06/14)

N-BIPHENYLACYL THIAZOLIDINE-2,4-DIONE DERIVATIVES, THEIR SYNTHESIS AND USES
N- Biphenylacyl-thiazolidine-2,4-dione derivatives of the general formula (I); where in, Z1 and Z2 represent H, or together forms a chemical bond; R1 represents H, alkoxy, nitro, halo, hydroxy, optionally substituted amino group, - O- (CH2)n-N(R7)(R8), -O-(CH2)n-R9, wherein n is 0 to 5, -COOH, -CN, linear or branched alkyl, substituted alkyl, cycloalkyl, -S- R11 alkyl thio, acyl, aroyl, substituted or unsubstituted heterocyclic, alkoxy carbonyl, aryloxy, aryloxy carbonyl; R2 represents H, halo, hydroxy, linear or branched alkyl, substituted alkyl; R3, R4, R5 independently represents H, alkoxy, hydroxy, linear or branched alkyl, substituted alkyl; R6 represents H, -COOH, linear or branched alkyl, -CN, -SO3H, optionally substituted amino group; R7 represents H, linear or branched alkyl, cyclo alkyl, acyl, aroyl, aralkyl where in aryl moiety is substituted or unsubstituted, or an aryl; R8 represents a substituted or unsubstituted heterocyclic, linear or branched alkyl, substituted alkyl; R9 represents a substituted or unsubstituted heterocyclic, substituted or unsubstituted aromatic, substituted or unsubstituted cycloalkyl, fused aryl-heterocyclyl; when R1 represents alkoxy group, and Z1 and Z2 together forms a chemical bond then, R2 or R3 or R4 or R5 is other than H, and when R1, R2, R3, R4, R5 are each independently represents H, and Z1 and Z2 together forms a chemical bond then R6 is not H; And when R1, R2, R3, R4, R5 represents independently or together halo group and - Z1 and Z2 together forms a chemical bond, then R6 is not H; are novel compounds, their isomers and their enantiomers and their pharmaceutically acceptable salts or solvates and their pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicines and process for preparing the same.
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(2010/08/08)