- Synthesis and structure-activity relationship studies of 2,4-thiazolidinediones and analogous heterocycles as inhibitors of dihydrodipicolinate synthase
-
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.
-
supporting information
(2021/11/27)
-
- Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents
-
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
-
-
- HETEROCYCLIC INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY
-
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
- -
-
Paragraph 0201
(2018/11/10)
-
- Exploration of some thiazolidine-2,4-dione and 2-oxoindoline derivatives incorporating 3,4,5-trimethoxybenzyl moiety as novel anticancer agents
-
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
-
p. 375 - 387
(2018/04/20)
-
- 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
-
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
-
supporting information
p. 7613 - 7616
(2018/07/15)
-
- Woollins’ reagent promotes selective reduction of α,β-unsaturated thiazo and selenazolidinones
-
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
-
p. 1445 - 1447
(2017/03/23)
-
- 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
-
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
-
p. 543 - 552
(2017/08/15)
-
- Reaction pathway of POCl3-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione
-
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
-
p. 857 - 866
(2016/07/06)
-
- Compound capable of inhibiting activity of NEDD8 kinase as well as preparation method and pharmaceutical application of compound
-
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.
- -
-
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
-
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.
- -
-
Paragraph 0122; 0124; 0136
(2017/04/14)
-
- Microwave-Assisted condensation reactions of acetophenone derivatives and activated methylene compounds with aldehydes catalyzed by boric acid under solvent-free conditions
-
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
-
p. 11617 - 11631
(2015/08/06)
-
- Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts
-
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
-
p. 197 - 202
(2014/05/20)
-
- Acetic anhydride-promoted one-pot condensation of 2,4-thiazolidinedione with bisulfite adducts of aldehydes
-
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
-
p. 4585 - 4589
(2014/12/10)
-
- NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
-
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.
- -
-
Paragraph 0122-0124; 0130
(2014/02/16)
-
- Sonochemistry: A good, fast and clean method to promote the synthesis of 5-arylidene-2,4-thiazolidinediones
-
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)
-
- Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds
-
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)
-
- Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry
-
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.
-
supporting information; experimental part
p. 743 - 753
(2012/03/11)
-
- Design and synthesis of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as novel tyrosinase inhibitors
-
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
-
experimental part
p. 245 - 252
(2012/04/10)
-
- New thiazolidine-2,4-diones as antimicrobial and cytotoxic agent
-
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)
-
- Solvent-free synthesis of 5-benzylidene-2-thioxothiazolidin-4-ones and thiazolidine-2,4-diones catalysed by glycine under microwave irradiation
-
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
-
experimental part
p. 238 - 239
(2011/07/09)
-
- Synthesis of 5-arylidene-2,4-thiazolidinediones by Knoevenagel condensation catalyzed by baker's yeast
-
An ecofriendly baker's yeast catalyzed Knoevenagel condensation of aromatic aldehydes and active methylene compounds has been performed. The developed protocol has been found to be applicable for obtaining 5-arylidene-2,4- thiazolidinediones, the precursors of hypoglycemic agents. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011.
- Pratap, Umesh R.,Jawale, Dhanaji V.,Waghmare, Rahul A.,Lingampalle, Dinesh L.,Mane, Ramrao A.
-
experimental part
p. 49 - 51
(2011/04/14)
-
- Synthesis, glucose uptake activity and structure-activity relationships of some novel glitazones incorporated with glycine, aromatic and alicyclic amine moieties via two carbon acyl linker
-
Three series of novel glitazones were designed and prepared by using appropriate synthetic schemes to incorporate glycine, aromatic and alicyclic amines via two carbon linker. Compounds were synthesized both under conventional and microwave methods. Nineteen out of twenty four synthesized compounds were evaluated for their in vitro glucose uptake activity using isolated rat hemi-diaphragm. Compounds, 6, 9a, 13a, 13b, 13c, 13f and 13h exhibited significant glucose uptake activity. Illustration about their synthesis and in vitro glucose uptake activity is described along with the structure-activity relationships.
- Kumar, B.R. Prashantha,Soni, Mukesh,Kumar, S. Santhosh,Singh, Kuldeep,Patil, Mohan,Baig, R.B. Nasir,Adhikary, Laxmi
-
experimental part
p. 835 - 844
(2011/04/16)
-
- Design, synthesis and characterization of some novel 3-coumarinyl- 5-aryliden-1,3-thiazolidine-2,4-diones and their antioxidant activity
-
In our effort to obtain biologically active compounds, new 3,5-disubstituted 1,3-thiazolidine-2,4- diones (5a - r) were synthesized. A series of 5-arylmethylidene-1,3-thiazolidine-2,4-diones (3a - r) were prepared by Knoevenagel reaction from 1,3-thiazolidine-2,4-dione (2) and appropriate aromatic aldehydes. Condensation of 3a - r with 7-hydroxy-4-bromomethyl-2-oxo- 2H-chromene (1) afforded novel 3-(7-hydroxy-2-oxo-2H-chromen-4-ylmethyl)-5- arylidene-1,3-thiazolidine-2,4-diones 5a - r. Compounds 3a - r and 5a - r were evaluated for their antioxidant activity (DPPH free radical scavenging activity).
- Cacic, Milan,Molnar, Maja
-
experimental part
p. 177 - 183
(2011/05/06)
-
- Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice
-
A large amount of evidence suggests that monocytes/macrophages infiltration is implicated in a variety of inflammatory diseases including acute liver injury. Monocyte chemoattractant protein 1 (MCP-1) plays a crucial role in the process of macrophages recruitment. We herein presented a small-molecule library and a feasible quick screening method of evaluating potency of inhibition of chemotaxis of RAW264.7 cells stimulated by MCP-1. Fifty-three small molecules were synthesized and screened, and four compounds (2g, 2h, 4f, and 6h) showed inhibitory effects with IC50 values range from 0.72 to 20.47 μM, with compound 4f being the most efficient. Further in vivo studies demonstrated that oral administration of 2g, 2h, 4f, or 6h decreases, most significantly for 4f, the serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) in ConA-induced acute livery injury BALB/c mice. Histopathological evaluation liver sections confirmed 4f as a potent, orally active compound for hepatoprotective effects against ConA-induced acute liver injury in BALB/c mice.
- Luo, Youfu,Ma, Liang,Zheng, Hao,Chen, Lijuan,Li, Rui,He, Chunmei,Yang, Shengyong,Ye, Xia,Chen, Zhizhi,Li, Zicheng,Gao, Yan,Han, Jing,He, Gu,Yang, Li,Wei, Yuquan
-
experimental part
p. 273 - 281
(2010/05/02)
-
- Identification of new non-carboxylic acid containing inhibitors of aldose reductase
-
Non-carboxylic acid containing bioisosteres of (5-arylidene-2,4-dioxothiazolidin-3-yl)acetic acids, which are active as aldose reductase (ALR2) inhibitors, were designed by replacing the carboxylic group with the trifluoromethyl ketone moiety. The in vitr
- Maccari, Rosanna,Ciurleo, Rosella,Giglio, Marco,Cappiello, Mario,Moschini, Roberta,Corso, Antonella Del,Mura, Umberto,Ottanà, Rosaria
-
scheme or table
p. 4049 - 4055
(2010/08/06)
-
- A convenient synthesis of 5-arylidenethiazolidine-2,4-diones catalyzed by alkaline ionic liquid
-
A series of 5-arylidenethiazolidine-2,4-diones was synthesized by the Knoevenagel condensation of thiazolidine-2,4-dione with aromatic aldehydes with alkaline ionic liquid l-butyl-3-mefhylimidazolium hydroxide ([bmim]OH) as dual solvent and catalyst. This
- Hu, Yi,Xie, Tao,Fu, Kai-Mei,Kang, Hui,Wei, Ping,Huang, He
-
experimental part
p. 757 - 761
(2009/06/18)
-
- Synthesis and evaluation of novel inhibitors of pim-1 and pim-2 protein kinases
-
The Pim protein kinases are frequently overexpressed in prostate cancer and certain forms of leukemia and lymphoma. 5-(3-Trifluoromethylbenzylidene) thiazolidine-2,4-dione (4a) was identified by screening to be a Pim-1 inhibitor and was found to attenuate the autophosphorylation of tagged Pim-1 in intact cells. Although 4a is a competitive inhibitor with respect to ATP, a screen of approximately 50 diverse protein kinases demonstrated that it has high selectivity for Pim kinases. Computational docking of 4a to Pim-1 provided a model for lead optimization, and a series of substituted thiazolidine-2,4-dione congeners was synthesized. The most potent new compounds exhibited IC 50s of 13 nM for Pim-1 and 2.3 μM for Pim-2. Additional compounds in the series demonstrated selectivities of more than 2500-fold and 400-fold for Pim-1 or Pim- 2, respectively, while other congeners were essentially equally potent toward the two isozymes. Overall, these compounds are new Pim kinase inhibitors that may provide leads to novel anticancer agents.
- Xia, Zuping,Knaak, Christian,Jian, Ma.,Beharry, Zanna M.,McInnes, Campbell,Wang, Wenxue,Kraft, Andrew S.,Smith, Charles D.
-
experimental part
p. 74 - 86
(2009/09/25)
-
- Synthesis and in vitro anticancer activity of 2,4-azolidinedione-acetic acids derivatives
-
The synthesis and evaluation of anticancer activity of 2,4-thia(imida)zolidinedione-3- and 5-acetic acids amides were described. The structures of compounds were determined by IR, 1H NMR, and MS analysis. In vitro anticancer activity of these compounds has been tested in National Cancer Institute (NCI) and the relationships between structure and anticancer activity are discussed. Among 2,4-azolidinedione-acetic acids derivatives 2-[5-(4-chlorobenzylidene)-2,4-dioxo-imidazolidin-3-yl]-N-(2-trifluoromethyl-phenyl)-acetamide (Ic) was superior to other related compounds in terms of high selectivity for the leukemia CCRF-CEM (log GI50 = -6.06), HL-60(TB) (log GI50 = -6.53), MOLT-4 (log GI50 = -6.52) and SR (log GI50 = -6.51) cell lines.
- Kaminskyy, Danylo,Zimenkovsky, Borys,Lesyk, Roman
-
scheme or table
p. 3627 - 3636
(2009/12/04)
-
- Synthesis, induced-fit docking investigations, and in vitro aldose reductase inhibitory activity of non-carboxylic acid containing 2,4-thiazolidinedione derivatives
-
In continuation of our studies, we here report a series of non-carboxylic acid containing 2,4-thiazolidinedione derivatives, analogues of previously synthesized carboxylic acids which we had found to be very active in vitro aldose reductase (ALR2) inhibit
- Maccari, Rosanna,Ottana, Rosaria,Ciurleo, Rosella,Rakowitz, Dietmar,Matuszczak, Barbara,Laggner, Christian,Langer, Thierry
-
p. 5840 - 5852
(2008/12/22)
-
- PHARMACEUTICAL PREPARATIONS COMPRISING INSULIN, ZINC IONS AND A ZINC-BINDING LIGAND
-
Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.
- -
-
Page/Page column 131
(2008/06/13)
-
- PHAMACEUTICAL PREPARATIONS COMPRISING INSULIN
-
Novel preparations comprising ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer wherein the ligand is extended by protamine that are capable of prolonging the ac-tion of insulin preparations.
- -
-
Page/Page column 126
(2010/02/15)
-
- Stabilised insulin compositions
-
The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.
- -
-
Page/Page column 51
(2008/06/13)
-
- Synthesis of 5-arylidene-3-(4′-bromobenzyl)thiazolidine-2,4-diones
-
Potential antihistamines 5-arylidene-3-(4′-bromobenzyl)thiazolidine- 2,4-diones were synthesized using 5-arylidenethiazolidine-2,4-dione potassium salt and 4-bromobenzyl bromide in dry acetone. The log P values are given for all the synthesized compounds.
- Popov-Pergal,Pergal,Csanadi,Djokovic
-
p. 1529 - 1533
(2007/10/03)
-
- Structure-activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium
-
Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities.
- Fan, Yun-Hua,Chen, Han,Natarajan, Amarnath,Guo, Yuhong,Harbinski, Fred,Iyasere, Julia,Christ, William,Aktas, Huseyin,Halperin, Jose A.
-
p. 2547 - 2550
(2007/10/03)
-
- PHARMACEUTICAL PREPARATIONS COMPRISING ACID-STABILISED INSULIN
-
Novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.
- -
-
Page/Page column 123
(2010/02/08)
-
- Novel ligands for the hisb10 zn2+ sites of the r-state insulin hexamer
-
Novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.
- -
-
-
- A convenient synthesis of 5-benzylidenethiazolidine-2, 4-diones under microwave irradiation without solvent
-
A series of 5-benzylidenethiazolidine-2,4-diones was synthesised by the Knoevenagel condensation of aromatic aldehydes with thiazolidine-2,4-dione in the presence of catalytic amounts of piperidine and acetic acid under microwave irradiation without solvent in good yields.
- Yang, De-Hong,Chen, Zhen-Chu,Chen, Song-Ying,Zheng, Qin-Guo
-
p. 330 - 331
(2007/10/03)
-
- Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
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The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
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Page 3; sheet 26
(2010/02/03)
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- Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones
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Several (Z)-5-arylidene-2,4- hiazolidinediones were synthesized and tested as aldose reductase inhibitors (ARIs). The most active of the N-unsubstituted derivatives (2) exerted the same inhibitory activity of Sorbinil. The introduction of an acetic side chain on N-3 of the thiazolidinedione moiety led to a marked increase in lending inhibitory activi y, conducting to the discovery of a very potent ARI (4c), whose activity level (IC50 =0.1 μM) was in the same range of Tolrestat . Moreover, the corresponding methyl esters (3), devoid of any acidic functionality, showed appreciable inhibitory activity similar to that of the N-unsubstituted compounds. It was also found that the substitution pattern on the 5-benzylidene moiety markedly influenced the activity of N-unsubstituted 2,4-thiazolidinediones 2, compounds with substituents at the meta position being generally more effective than the para-substituted ones; however, this SAR was not evidenced in acetates 3 and acids 4. Copyright
- Bruno,Costantino,Curinga,Maccari,Monforte,Nicolo,Ottana,Vigorita
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p. 1077 - 1084
(2007/10/03)
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- Regiospecific reduction of 5-benzylidene-2,4-thiazolidinediones and 4- oxo-2-thiazolidinethiones using lithium borohydride in pyridine and tetrahydrofuran
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The novel regiospecific and general reduction of 5-benzylidene-2,4- thiazolidinediones and 5-benzylidene-4-oxo-2-thiazolidinethiones to the corresponding 5-benzyl derivatives has been accomplished using lithium borohydride in pyridine and tetrahydrofuran. Sodium borohydride and lithium chloride can also be used under these conditions, which represents a cheaper alternative to lithium borohydride. (C) 2000 Elsevier Science Ltd.
- Giles, Robert G.,Lewis, Norman J.,Quick, John K.,Sasse, Michael J.,Urquhart, Michael W. J.,Youssef, Latifa
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p. 4531 - 4537
(2007/10/03)
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- Intermolecular Hydrogen Bonds of 5-Benzylidene-2,4-thiazolidinedione Derivatives and Related Compounds in Crystalline State
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From the viewpoint of noncentrosymmetric molecular arrangement design in crystalline state, which is indispensable to second order nonlinear optical materials, intermolecular hydrogen bond formation of eight 5-benzylidene-2,4-thiazolidinedione derivatives and related compounds were investigated by X-ray crystallography. 5-Benzylidene-2,4-thiazolidinedione (1) itself forms centrosymmetric head-to-head (or tail-to-tail) intermolecular hydrogen bonds and takes a centrosymmetric molecular arrangement in crystalline state. Introduction of 4-methoxy group into the phenyl moiety of 1 was the only useful means for head-to-tail type intermolecular hydrogen bond formation. 5-(4-Methoxybenzylidene)-2,4-thiazolidinedione shows head-to-tail type intermolecular hydrogen bonds and noncentrosymmetric molecular arrangement in crystalline state. Similarities in both hydrogen bond formation and molecular arrangement in crystalline state are obtained by conversion of 2,4-thiazolidinedione to 2-thioxo-4-oxazolidinone, but in the case of conversion to 2, 4-oxazolidinedione only hydrogen bond formation is shown in a similar manner. In the case of conversion to rhodanine, no similarity in either hydrogen bond formation or molecular arrangement in crystalline state was shown. Such behaviors were considered from viewpoints of pKa and hydrogen bond energy.
- Okazaki, Masaki,Uchino, Nobuhiko,Ishihara, Makoto,Fukunaga, Hiroo
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p. 1713 - 1718
(2007/10/03)
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- CONDENSATION OF 2,4-DIOXOTETRAHYDRO-1,3-THIAZOLE WITH AROMATIC ALDEHYDES
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It was shown that the morpholine catalyzed condensation of 2,4-dioxotetrahydro-1,3-thiazole with aromatic aldehydes is a convenient preparative method for the preparation of 5-arylidene-2,4-dioxotetrahydro-1,3-thiazoles.The pesticidal activity of the synt
- Popov-Pergal, K.,Cekovic, Z.,Pergal, M.
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p. 1958 - 1962
(2007/10/02)
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