- Multicomponent assembling of imidazole N-oxides, aldehydes and CH-acids: A simple and efficient approach to newly functionalized imidazole derivatives
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An efficient and simple method for C2-functionalization of 2-unsubstituted imidazole N-oxides has been developed. It consists at the condensation of 2-unsubstituted imidazole N-oxides with aldehydes and CH-acids. This method permits broad variations in th
- Mityanov, Vitaly S.,Kutasevich, Anton V.,Krayushkin, Michail M.,Lichitsky, Boris V.,Dudinov, Arkady A.,Komogortsev, Andrey N.,Koldaeva, Tatyana Yu.,Perevalov, Valery P.
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- Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms
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Different 2,4-thiazolidinedione-tethered coumarins 5a–b, 10a–n and 11a–d were synthesised and evaluated for their inhibitory action against the cancer-associated hCAs IX and XII, as well as the physiologically dominant hCAs I and II to explore their selec
- Eldehna, Wagdy M.,Taghour, Mohammed S.,Al-Warhi, Tarfah,Nocentini, Alessio,Elbadawi, Mostafa M.,Mahdy, Hazem A.,Abdelrahman, Mohamed A.,Alotaibi, Ohoud J.,Aljaeed, Nada,Elimam, Diaaeldin M.,Afarinkia, Kamyar,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
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p. 531 - 541
(2022/01/13)
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- Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase
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Dihydrodipicolinate synthase (DHDPS), responsible for the first committed step of the diaminopimelate pathway for lysine biosynthesis, has become an attractive target for the development of new antibacterial and herbicidal agents. Herein, we report the di
- Christoff, Rebecca M.,Soares da Costa, Tatiana P.,Bayat, Saadi,Holien, Jessica K.,Perugini, Matthew A.,Abbott, Belinda M.
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supporting information
(2021/11/27)
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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
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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
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- Biological Prediction from Computational Approach, Synthesis, and Biological Evaluations of Newer Thiazolidine-2,4-dione Conjugates
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Thiazolidine-2,4-dione is a toxophoric unit and its derivatives act as antimicrobial and antitubercular agents. Computational approach two-dimensional quantitative structure-activity relationship (2D-QSAR) was used to predict antitubercular activity of the thizolidine-2,4-dione derivatives. 2D-QSARS generated model using partial least squares regression method which predicted the statistically significant r2 = 0.3868, q2= 0.0193, pred_r2 = 0.5240, and F test = 3.7855. 2D-QSAR model equation denoted log(1/MIC) of the antitubercular activity correlated with thermodynamic descriptor SAMost Hydrophobic Hydrophilic Distance. Biological predicted derivatives of thiazolidine-2,4-dione (Z)-N-(2-(2,4-dichlorophenoxy)phenyl)-2-(5-substitutidene-2,4-dioxothiazolidin-3-yl)acetamide (C1-C10) were synthesized and spectrally evicted from IR, 1H NMR, 13C NMR and Mass spectral data analysis as well as biologically evaluated against antitubercular and antimicrobial activities. From the biologically evaluated derivatives, compounds C1, C2, C3 and C6 were found to be active against the different antimicrobial species. Compounds C1, C3 and C10 are more progressive than others against antitubercular species.
- Patel, Jaydeep A.,Patel, Navin B.,Tople, Manesh S.
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p. 379 - 387
(2021/11/22)
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- Synthesis and antimicrobial activity of a new series of thiazolidine-2,4-diones carboxamide and amino acid derivatives
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Novel thiazolidine-2,4-dione carboxamide and amino acid derivatives were synthesized in excellent yield using OxymaPure/N,N'-diisopropylcarbodimide coupling methodology and were characterized by chromatographic and spectrometric methods, and elemental ana
- Alhameed, Rakia Abd,Almarhoon, Zainab,Bukhari, Sarah I.,El-Faham, Ayman,De La Torre, Beatriz G.,Albericio, Fernando
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- A class of carbonic anhydrase IX/XII–selective carboxylate inhibitors
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A small series of 2,4-dioxothiazolidinyl acetic acids was prepared from thiourea, chloroacetic acid, aromatic aldehydes, and ethyl-2-bromoacetate. They were assayed for the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isoforms of human (h) origin, the cytosolic hCA I and II, and the transmembrane hCA IX and XII, involved among others in tumorigenesis (hCA IX and XII) and glaucoma (hCA II and XII). The two cytosolic isoforms were not inhibited by these carboxylates, which were also rather ineffective as hCA IX inhibitors. On the other hand, they showed submicromolar hCA XII inhibition, with KIs in the range of 0.30–0.93 μM, making them highly CA XII-selective inhibitors.
- Alhameed, Rakia Abd,Almarhoon, Zainab,Berrino, Emanuela,El-Faham, Ayman,Supuran, Claudiu T.
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p. 549 - 554
(2020/02/13)
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- Synthesis and anti-diabetic activity evaluation of phosphonates containing thiazolidinedione moiety
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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
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p. 586 - 591
(2020/03/23)
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- Design, synthesis and in vitro antiproliferative activity of new thiazolidinedione-1,3,4-oxadiazole hybrids as thymidylate synthase inhibitors
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Thymidylate synthase (TS) has been an attention-grabbing area of research for the treatment of cancers due to their role in DNA biosynthesis. In the present study, we have synthesised a library of thiazolidinedione-1,3,4-oxadiazole hybrids as TS inhibitors. All the synthesised hybrids followed Lipinski and Veber rules which indicated good drug likeness properties upon oral administration. Among the synthesised hybrids, compound 9 and 10 displayed 4.5 and 4.4 folds activity of 5-Fluorouracil, respectively against MCF-7 cell line whereas 3.1 and 2.5 folds cytotoxicity against HCT-116 cell line. Furthermore, compound 9 and 10 also inhibited TS enzyme with IC50 = 1.67 and 2.21 μM, respectively. Finally, the docking studies of 9 and 10 were found to be consistent with in vitro TS results. From these studies, compound 9 and 10 has the potential to be developed as TS inhibitors.
- Alam, Mohammad Mahboob,Alzhrani, Zohor Mohammad Mahdi,Nazreen, Syed,Neamatallah, Thikryat
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p. 1116 - 1123
(2020/05/13)
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- 5-(4-Methoxybenzylidene)thiazolidine-2,4-dione-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations
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A novel series of 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives, 5a–g and 7a–f, was designed, synthesized, and evaluated for their anticancer activity against HepG2, HCT116, and MCF-7 cells. HepG2 and HCT116 were the most sensitive cell lines to the influence of the new derivatives. In particular, compounds 7f, 7e, 7d, and 7c were found to be the most potent derivatives of all the tested compounds against the HepG2, HCT116, and MCF-7 cancer cell lines. Compound 7f (IC50 = 6.19 ± 0.5, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively) exhibited a higher activity than sorafenib (IC50 = 9.18 ± 0.6, 8.37 ± 0.7, and 5.10 ± 0.4 μM, respectively) against HepG2 and MCF-7, cells but a lower activity against HCT116 cancer cells, respectively. Also, this compound displayed a higher activity than doxorubicin (IC50 = 7.94 ± 0.6, 8.07 ± 0.8, and 6.75 ± 0.4 μM, respectively) against HepG2 and MCF-7 cells, but nearly the same activity against HCT116 cells, respectively. All derivatives, 5a–g and 7a–f, were evaluated for their inhibitory activities against vascular endothelial growth factor receptor-2 (VEGFR-2). Among them, compound 7f was found to be the most potent derivative that inhibited VEGFR-2 at an IC50 value of 0.12 ± 0.02 μM, which is nearly the same as that of sorafenib (IC50 = 0.10 ± 0.02 μM). Compounds 7e, 7d, 7c, and 7b exhibited the highest activity, with IC50 values of 0.13 ± 0.02, 0.14 ± 0.02, 0.14 ± 0.02, and 0.18 ± 0.03 μM, respectively, which are more than the half of that of sorafenib. Furthermore, molecular docking was performed to investigate their binding mode and affinities toward the VEGFR-2 receptor. The data obtained from the docking studies highly correlated with those obtained from the biological screening.
- El-Adl, Khaled,Sakr, Helmy,Nasser, Mohamed,Alswah, Mohamed,Shoman, Fatma M. A.
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- Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents
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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.
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- Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents
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In an effort to improve the antimicrobial activity of norfloxacin, a series of hybrid norfloxacin–thiazolidinedione molecules were synthesized and screened for their direct antimicrobial activity and their anti-biofilm properties. The new hybrids were intended to have a new binding mode to DNA gyrase, that will allow for a more potent antibacterial effect, and for activity against current quinolone-resistant bacterial strains. Moreover, the thiazolidinedione moiety aimed to include additional anti-pathogenicity by preventing biofilm formation. The resulting compounds showed promising direct activity against Gram-negative strains, and anti-biofilm activity against Gram-positive strains. Docking studies and ADMET were also used in order to explain the biological properties and revealed some potential advantages over the parent molecule norfloxacin.
- Marc, Gabriel,Araniciu, C?t?lin,Oniga, Smaranda Dafina,Vlase, Laurian,P?rn?u, Adrian,Nad??, George Cosmin,Novac, Cristiana ?tefania,Matei, Ioana Adriana,Chifiriuc, Mariana Carmen,M?ru?escu, Lumini?a,Oniga, Ovidiu
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- Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives
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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.
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p. 164 - 172
(2018/12/13)
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- Anti-hepatitis-C virus activity and QSAR study of certain thiazolidinone and thiazolotriazine derivatives as potential NS5B polymerase inhibitors
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The present study reports on evaluation of anti-HCV activity and QSAR of certain arylidenethiazolidinone derivatives as potential inhibitors of HCV-NS5B polymerase. The pursued compounds involving, 5-aryliden-3-arylacetamidothiazolidin-2,4-diones 4–6(a–f), 5-arylidine-2-(N-arylacetamido)-iminothiazolidin-4-one (10) and their rigid counterparts 5-arylidinethiazolotriazines 13–15(a–f), were synthesized and their structures confirmed by spectral and elemental analyses. The results of NS5B polymerase inhibition assay revealed compound 4e, as the most active inhibitor (IC50 = 0.035 μM), which is four folds greater than that of the reference agent, VCH-759, (IC50 = 0.14 μM). Meanwhile, compounds 4b, 4c, 5a, and 5c, and 13b, 14e and 15c displayed equipotency to 2 folds higher activity than VCH-759 (IC50 values: 0.085, 0.14, 0.14, 0.10, 0.12, 0.09 and 0.07 μM, respectively). Assessment of the anti-HCV activity (GT1a) using human hepatoma cell line (Huh-7.5) illustrates superior activity of 4e (EC50 = 3.80 μM) relative to VCH-759 (EC50 = 5.29 μM). Cytotoxicity evaluation on, Transformed normal cell lines (Human Liver Epithelial-2, THLE-2 and Proximal Tubular Epithelial, RPTEC/TERT1), demonstrate enhanced safety profile of 4e (CC50 = 102.77, 161.37 μM, respectively) compared to VCH-759 (CC50 = 61.83, 81.28 μM, respectively). Molecular docking of the synthesized derivatives to NS5B polymerase allosteric site (PDB: 2HWH) showed similar binding modes to that of the co-crystallized ligand. Moreover, QSAR models were established for the studied thiazolidinones and thiazolotriazines to investigate the molecular characteristics contributing to the observed NS5B polymerase inhibition activity. The obtained results inspire further investigations of thiazolidinones and thiazolotriazine aiming at affording more potent, safe and orally active non-nucleoside NS5B polymerase inhibitors as anti-HCV drug candidates.
- Hassan, Ghaneya S.,Georgey, Hanan H.,Mohammed, Esraa Z.,Omar, Farghaly A.
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- HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
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The present invention relates to certain heterocyclic compounds of formula (1) that have the ability to inhibit lysine biosynthesis via the diaminopimelate biosynthesis pathway in certain organisms. As a result of this activity these compounds can be used
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Paragraph 0201
(2018/11/10)
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- Exploration of some thiazolidine-2,4-dione and 2-oxoindoline derivatives incorporating 3,4,5-trimethoxybenzyl moiety as novel anticancer agents
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Background: Combrestastatin A-4 (CA-4) is a potent anticneoplastic and antiangiogenesis natural substance isolated from Combretum caffrum. Over the past two decades, numerous derivatives of CA-4 have been discovered. However, none of these derivatives has reached the clinical stage. Thus, continuing effort is needed in developing CA-4 analogues with improved pharmacological properties. Methods: In this study, two series of thiazolidine-2,4-dione and 2-oxoindoline derivatives incorporating 3,4,5-trimethoxybenzyl scaffold were designed and synthesized as CA-4 analogues. Results: Numerous CA-4 analogues bearing thiazolidine-2,4-dione/2-oxoindoline have been synthesized. These compounds were evaluated against several human cancer cell lines. It was found that a series of 5/7-substituted-1-(3,4,5-trimethoxy)benzylindoline-2,3-diones (2a-g) exhibited significant cytotoxicity. Especially compound 2d bearing a 5-bromo substituent showed the best activity with IC50 values in sub-microgram/mL scale in four human cancer cell lines tested. This compound also exhibited potent tubulin polymerization inhibitory activity. A series of (Z)-5-arylidene-3-(3,4,5-trimethoxybenzyl)thiazolidine-2,4-diones (6a-j), on the other hand, displayed only moderate cytotoxic activities with only compound 6a showing comparable cytotoxicity to 2d. Finally, in silico molecular modeling and drug-likeness profiling revealed that five compounds 2b, 2d, 2e, 3e and 6a bound to tubulin active binding sites with strong binding affinities. Conclusion: This study discovered some novel CA-4 analogues with cytotoxic potency and antitubulin activity acceptable to be further developed as effective anticancer drug candidates.
- Huan, Le Cong,Pham-The, Hai,Le-Thi-Thu, Huong,Thao, Tran Phuong,Que, Do Nguyet,Trang, Nguyen-Thu,Dung, Phan Thi Phuong,Pyo, Minji,Han, Sang-Bae,Thuan, Nguyen Thi,Nam, Nguyen-Hai
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p. 375 - 387
(2018/04/20)
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- Discovery and synthesis of the first selective BAG domain modulator of BAG3 as an attractive candidate for the development of a new class of chemotherapeutics
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BAG3 protein has emerged as a key regulator of important cellular processes and its expression is increased in some tumor types; however, despite its potential value for future chemotherapeutics, no selective BAG3 modulators have been yet reported. Here we report the 2,4-thiazolidinedione derivative 28 as the first BAG3 protein modulator.
- Terracciano, Stefania,Lauro, Gianluigi,Russo, Alessandra,Vaccaro, Maria Carmela,Vassallo, Antonio,De Marco, Margot,Ranieri, Bianca,Rosati, Alessandra,Turco, Maria Caterina,Riccio, Raffaele,Bifulco, Giuseppe,Bruno, Ines
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supporting information
p. 7613 - 7616
(2018/07/15)
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- Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium
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Abstract: TS-1 zeolite was prepared for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium by incorporating titanium(IV) cations in a silicate-1 framework using hydrothermal treatment and characterized by using XRD, EDX, BET, FT-IR and SEM techniques. The catalytic activity of the catalyst was tested for Knoevenagel condensation reaction. The condensation of active ethylene 2,4-thiazolidinedione with substituted aryl aldehydes under aqueous medium at 90?°C afforded the corresponding product in excellent yield up to 92% within 30?min. The present method offers several advantages over the reported methods such as easy separation of catalyst, simple work-up procedure, and an excellent yield of desired product. Furthermore, the catalyst could be reused without significant loss in activity. Graphical abstract: [Figure not available: see fulltext.]
- Gadekar, Sachin P.,Dipake, Sudarshan S.,Gaikwad, Suresh T.,Lande, Machhindra K.
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p. 7509 - 7518
(2018/09/06)
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- Woollins’ reagent promotes selective reduction of α,β-unsaturated thiazo and selenazolidinones
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In this work we describe the Woollins’ reagent as useful for the selective reduction of the double bond of 2-α,β-unsaturated thiazo and selenazolidinones. The reaction took place in toluene at room temperature to give the corresponding saturated heterocyc
- Pizzo, Chiara,Mahler, Graciela
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p. 1445 - 1447
(2017/03/23)
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- Copper(II)-complex functionalized magnetite nanoparticles: a highly efficient heterogeneous nanocatalyst for the synthesis of 5-arylidenthiazolidine-2,4-diones and 5-arylidene-2-thioxothiazolidin-4-one
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Abstract: Magnetite nanoparticles (MNPs) have proved to be a useful support for heterogeneous catalysis. We have synthesized Fe3O4 MNPs functionalized with a copper(II) complex, and tested the resulting material as a heterogeneous nanocatalyst. The catalyst was tested for aldol condensation reactions between aliphatic/aromatic aldehydes and rhodanine or thiazolidine-2,4-dione (TZD) derivatives under reflux in ethanol, giving the target products in high yield. Environmentally benign chemistry, short reaction times, simple work-up, excellent yields, and the reusability of the new nanocatalyst are beneficial features of the present study. The nanocatalyst was characterized by scanning electron microscopy, vibrating sample magnetometery, thermogravimetry, X-ray diffraction, and energy-dispersive X-ray analyses. The data showed that the magnetic nanoparticles are super-paramagnetic with a size range of 10–20?nm. Graphical Abstract: [Figure not available: see fulltext.].
- Akhavan, Malihe,Foroughifar, Naser,Pasdar, Hoda,Khajeh-Amiri, Alireza,Bekhradnia, Ahmadreza
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p. 543 - 552
(2017/08/15)
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- Knoevenagel condensation catalyzed by novel Nmm-based ionic liquids in water
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A series of novel N-methyl morpholine (Nmm) based ionic liquids with 1,2-propanediol group were synthesized and used as catalysts for Knoevenagel condensation at room temperature in water. Under the effect of the catalyst, various aldehydes or aliphatic ketones could react with a wide range of activated methylene compounds well, including malononitrile, alkyl cyanoacetate, cyanoacetamide, β-diketone, barbituric acid, 2-arylacetonitrile and thiazolidinedione. Furthermore, most of the products could be separated just by filtrating and washing with water. Additionally, the catalyst is recyclable and applicable for the large-scale synthesis.
- Xu, Hao,Pan, Liyang,Fang, Xiaomin,Liu, Baoying,Zhang, Wenkai,Lu, Minghua,Xu, Yuanqing,Ding, Tao,Chang, Haibo
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supporting information
p. 2360 - 2365
(2017/05/29)
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- New Route for the Synthesis of Thiazolidine 2,4dione Azepine Derivatives
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A new facile ionic liquid mediated proficient method is developed for the synthesis of structurally new thiazepine and oxazepine derivatives of thiazolidine 2,4-dione. This protocol proceeds through, one-pot three component reaction between fused cyclic k
- Kommidi, Devendar Reddy,Pagadala, Ramakanth,Varkolu, Mohan,Koorbanally, Neil A.,Moodley, Brenda
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p. 1071 - 1076
(2017/03/27)
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- Novel 2,4- thiazolidinediones: Synthesis, in?vitro cytotoxic activity, and mechanistic investigation
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Two thiazolidinedione scaffolds different in the position of the thiazolidinedione ring in the molecule were tested for in?vitro cytotoxic activity in a panel of human cancer cell lines namely, prostate cancer cells PC-3, breast carcinoma cells MDA-MB-231
- Metwally, Kamel,Pratsinis, Harris,Kletsas, Dimitris
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p. 340 - 350
(2017/04/13)
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- Reaction pathway of POCl3-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione
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We investigated the POCl3-mediated transformation of aromatic bisulfite adducts to the corresponding 5- arylidenethiazolidine-2,4-diones. The in situ transformation of an aromatic bisulfite adduct to the parent aldehyde in a non-aqueous non-pol
- Mohanty, Sandeep,Roy, Amrendra Kumar,Reddy, Sandeep,Kumar, Kuchipudi Pavithran Vinay,Karmakar, Arun Chandra
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p. 857 - 866
(2016/07/06)
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- Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound
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The invention belongs to the field of medicines and in particular relates to a compound with the structure of a formula I, a stereomer of the compound or pharmaceutically acceptable salts of the compound as well as a preparation method of the compound and application of the compound to preparation of anti-tumor medicines. A pharmacological experiment result shows that the compound can be used for inhibiting the activity of NEDD8 kinase and has the inhibition effect on proliferation of a plurality of types of tumor cells, so that the compound can be used as an NEDD8 kinase activity inhibitor for preparing the anti-tumor medicines. The formula I is shown in the description.
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Paragraph 0072; 0073; 0074; 0139; 0140; 0141
(2016/10/10)
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- New compounds having skin whitening, antioxidant and PPAR activity, and medical use thereof
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PURPOSE: A novel compound with skin whitening, antioxidation, and PPAR activation effects, and a medical use thereof are provided to be used for a pharmaceutical composition or a cosmetic product. CONSTITUTION: A compound is denoted by chemical formula 1. A skin whitening composition contains the compound as an active ingredient. An antioxidative composition for preventing or treating oxidative diseases contains the compound of chemical formula 1 as an active ingredient. The oxidative diseases are selected among skin aging, pigmentation, wrinkling, psoriasis, or eczema. The composition prevents or treats diseases which are regulated by PPAR(peroxisome proliferator-activated receptor) activity. The PPAR includes PPAR alpha or PPAR gamma.
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Paragraph 0122; 0124; 0136
(2017/04/14)
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- Composition for Distructing Microalgae
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The present invention relates to a composition for disrupting microalgae. The composition for disrupting microalgae can suppress growth and proliferation of microalgae when treated in marine microalgae culture farms, areas where green or red tide takes pl
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Paragraph 0248-0253
(2017/04/12)
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- Design and synthesis of 4′-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methyl)biphenyl-2-carbonitrile analogs as bacterial peptide deformylase inhibitors
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Herein, we report the synthesis and screening of 4′-((5-benzylidene-2,4-dioxothiazolidin-3-yl)methyl)biphenyl-2-carbonitrile analogs 11(a–j) as bacterial peptide deformylase (PDF) enzyme inhibitors. The compounds 11b (IC50 value?=?139.28?μm), 11g (IC50 value?=?136.18?μm), and 11h (IC50 value?=?131.65?μm) had shown good PDF inhibition activity. The compounds 11b (MIC range?=?103.36–167.26?μg/mL), 11g (MIC range?=?93.75–145.67?μg/mL), and 11h (MIC range?=?63.61–126.63?μg/mL) had also shown potent antibacterial activity when compared with standard ampicillin (MIC range?=?100.00–250.00?μg/mL). Thus, the active derivatives were not only PDF inhibitors but also efficient antibacterial agents. To gain more insight on the binding mode of the compounds with PDF enzyme, the synthesized compounds 11(a–j) were docked against PDF enzyme of Escherichia coli and compounds exhibited good binding properties. The results suggest that this class of compounds has potential for development and use in future as antibacterial drugs.
- Khan, Firoz A. Kalam,Patil, Rajendra H.,Shinde, Devanand B.,Sangshetti, Jaiprakash N.
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p. 938 - 944
(2016/11/11)
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- Microwave-Assisted condensation reactions of acetophenone derivatives and activated methylene compounds with aldehydes catalyzed by boric acid under solvent-free conditions
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We here disclosed a new protocol for the condensation of acetophenone derivatives and active methylene compounds with aldehydes in the presence of boric acid under microwave conditions. Implementation of the reaction is simple, healthy and environmentally
- Brun, Elodie,Safer, Abdelmounaim,Carreaux, Franois,Bourahla, Khadidja,L'Helgoua'ch, Jean-Martial,Bazureau, Jean-Pierre,Villalgordo, Jose Manuel
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p. 11617 - 11631
(2015/08/06)
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- A simple, efficient and green procedure for knoevenagel condensation in hydroxy-functionalized ionic liquids
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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
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p. 1385 - 1397
(2015/07/15)
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- Synthesis and evaluation of thiazolidinedione-coumarin adducts as antidiabetic, anti-inflammatory and antioxidant agents
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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
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p. 429 - 445
(2016/03/25)
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- Multicomponent domino process for the synthesis of some novel 5-(arylidene)-3-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-thiazolidine-2,4-diones using PEG-400 as an efficient reaction medium and their antimicrobial evaluation
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A series of novel thiazolidinedione-triazole hybrids were synthesized by one pot reaction between thiazolidine-2,4-dione, substituted aryl aldehydes, propargyl bromide and substituted aryl azides using piperidine, CuSO4·5H2O and sodi
- Sindhu, Jayant,Singh, Harjinder,Khurana,Sharma, Chetan,Aneja
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- Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts
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The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4- thiazolidinedione's has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione's with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene) thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.
- Mohanty, Sandeep,Reddy. G, Sandeep,Karmakar, Arun Chandra
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p. 197 - 202
(2014/05/20)
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- Acetic anhydride-promoted one-pot condensation of 2,4-thiazolidinedione with bisulfite adducts of aldehydes
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We describe a simple and efficient one-pot method for condensing bisulfite adducts of aromatic aldehydes directly with 2,4-thiazolidinedione catalyzed by acetic anhydride. The two main highlights of this study are the one-pot condensation of bisulfite adducts with 2,4-thiazolidinedione in non-aqueous media and the use of Design of Experiment to understand and optimize the reaction conditions. This methodology was then generalized using other active methylene compounds, such as malononitrile.
- Mohanty, Sandeep,Roy, Amrendra Kumar,Kumar, Vinay K.P.,Reddy, Sandeep G.,Karmakar, Arun Chandra
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p. 4585 - 4589
(2014/12/10)
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- NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
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Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.
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Paragraph 0122-0124; 0130
(2014/02/16)
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- Sonochemistry: A good, fast and clean method to promote the synthesis of 5-arylidene-2,4-thiazolidinediones
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The efficient synthesis of sixteen 5-arylidene-2,4-thiazolidinediones by aldol condensation reaction of 2,4-thiazolidinedione, mono- and di-substituted arenealdehydes and KOH using ultrasound irradiation is reported. The desired compounds were obtained in
- Drawanz, Bruna B.,Ribeiro, Camila S.,Masteloto, Hellen G.,Neuenfeldt, Patrícia D.,Pereira, Claudio M.P.,Siqueira, Geonir M.,Cunico, Wilson
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p. 1615 - 1617
(2014/06/09)
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- Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds
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Δ2-Troglitazone derivatives were shown to exhibit anti-proliferative activity in a PPARγ-independent manner. We prepared various compounds in order to increase their potency and decrease their toxicity towards non-malignant primary cultured hepatocytes. Many compounds induced viabilities less than 20% at 10 μM on various cancer cell lines. Furthermore, five of them showed hepatocyte viability of 80% or more at 200 μM. In addition, compounds 17 and 18 exhibited promising maximum tolerated doses on a murine model, enabling future investigations.
- Bordessa, Andrea,Colin-Cassin, Christelle,Grillier-Vuissoz, Isabelle,Kuntz, Sandra,Mazerbourg, Sabine,Husson, Gauthier,Vo, Myriam,Flament, Stéphane,Martin, Hélène,Chapleur, Yves,Boisbrun, Michel
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p. 129 - 140
(2014/07/08)
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- Green synthesis of 5 arylidene-2,4-thiazolidinedione, 5-benzylidene rhodanine and dihydrothiophene derivatives catalyzed by hydrated ionic liquid tetrabutylammonium hydroxide in aqueous medium
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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
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p. 270 - 278
(2014/04/03)
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- Synthesis and antimicrobial activity of some new N-(aryloxoalkyl)-5- arylidene-thiazolidine-2,4-diones
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A series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione and 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives (3a-h and 5a-h, respectively) were synthesized starting from 5-arylidenethiazolidine- -2,4-dione and α-halo-ketones. The struc
- Stana, Anca,Tiperciuc, Brindusa,Duma, Mihaela,Pirnau, Adrian,Verite, Philippe,Oniga, Ovidiu
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p. 115 - 123
(2014/03/21)
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- Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry
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Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.
- Mendgen, Thomas,Steuer, Christian,Klein, Christian D.
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supporting information; experimental part
p. 743 - 753
(2012/03/11)
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- Design and synthesis of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as novel tyrosinase inhibitors
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In continuing our search for novel tyrosinase inhibitors, a series of 5-(substituted benzylidene)thiazolidine-2,4-diones were rationally designed and synthesized, and their inhibitory effects on mushroom tyrosinase activity were evaluated. Twelve target c
- Ha, Young Mi,Park, Yun Jung,Kim, Jin-Ah,Park, Daeui,Park, Ji Young,Lee, Hye Jin,Lee, Ji Yeon,Moon, Hyung Ryong,Chung, Hae Young
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experimental part
p. 245 - 252
(2012/04/10)
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- New thiazolidine-2,4-diones as antimicrobial and cytotoxic agent
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New (Z)-5-substituted-2,4-thiazolidinediones (3a-m) were easily prepared by the condensation of thiazolidine- 2,4-dione (1) with suitable aldehydes (2a-m) via microwave irradiation technique. The reaction between (Z)-5-substituted-2,4- thiazolidinediones and 4-(bromomethyl) benzoic acid, using potassium carbonate as base in refluxing acetone, followed by a workup in acidic medium provided 4-(((Z)-5-substituted-2,4-dioxothiazolidin-3- yl)methyl) benzoic acid derivatives (4a-m). The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR spectral studies, and elemental analysis. All compounds were evaluated for their in vitro antimicrobial and cytotoxic activities. Antibacterial and antifungal results revealed that most of the compounds showed significant activity where as compounds 4c and 4g are found to be broad spectrum antibacterial and antifungal properties, the MIC values were observed in the range of 2-4 and 2-8 μg/ ml, respectively. InMTTcytotoxicity studies, the compound 4g was found most potent. In HeLa, HT29, A549, and MCF-7 cells, the IC50 values were observed in the range of 30-36 μM. Springer Science+Business Media, LLC 2011.
- Alegaon, Shankar G.,Alagawadi, Kallanagouda R.
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p. 3214 - 3223
(2012/10/29)
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- Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
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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
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experimental part
p. 5388 - 5391
(2012/09/22)
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- Preparation of mg-doped Ce-Zr solid catalysts and their catalytic potency for the synthesis of 5-Arylidene-2,4-thiazolidinediones via knoevenagel condensation
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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
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p. 196 - 201
(2012/11/13)
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- Substituent and solvent effects on intramolecular charge transfer of 5-arylidene-2,4-thiazolidinediones
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The absorption spectra of twelve 5-arylidene-2,4-thiazolidinediones were recorded in twenty one solvents in the range from 300 to 600 nm. The effect of specific and non-specific solvent-solute interactions on the absorption maxima shifts were evaluated by
- Ran?i?, Milica,Tri?ovi?, Nemanja,Mil?i?, Milo?,U??umli?, Gordana,Marinkovi?, Aleksandar
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experimental part
p. 500 - 507
(2012/02/04)
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- Synthesis and evaluation of some novel 2,4-thiazolidinedione derivatives for antibacterial, antitubercular and antidiabetic activities
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A series of 2,4-thiazolidinedione have been synthesized and evaluated for antibacterial, antitubercular and antidiabetic activities. The newly synthesized compounds have been characterized by IR, 1H NMR and elemental analysis. All compounds have shown promising antibacterial, antitubercular and antidiabetic activities when compared with standard drug Norfloxacin, Streptomycin, and Glibenclamide respectively. Compounds 1a, 2a have shown promising antibacterial activity while compounds 1b, 2b have shown promising antitubercular activity and compounds 1a, 2a and 2c have shown promising antidiabetic activity.
- Pattan, Shashikant,Kedar, Manisha,Pattan, Jayashri,Dengale, Santosh,Sanap, Manjusha,Gharate, Utkarsha,Shinde, Punam,Kadam, Sushma
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p. 1421 - 1425
(2012/11/07)
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- NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
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The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.
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Page/Page column 18
(2011/11/12)
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- Solvent-free synthesis of 5-benzylidene-2-thioxothiazolidin-4-ones and thiazolidine-2,4-diones catalysed by glycine under microwave irradiation
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A novel and clean synthesis of 5-benzylidene-2-thioxothiazolidin-4-ones and thiazolidine-2,4-diones has been achieved in good yields by condensation of aromatic aldehydes with rhodanine or thiazolidine-2,4-dione under microwave irradiation using glycine a
- Yang, Ben-Yong,Yang, De-Hong
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experimental part
p. 238 - 239
(2011/07/09)
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