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5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione, also known as pioglitazone, is a chemical compound that belongs to the class of thiazolidinediones. It is commonly used as a medication for treating type 2 diabetes due to its anti-hyperglycemic and anti-inflammatory properties. Pioglitazone works by increasing the body's sensitivity to insulin, which helps in better control of blood sugar levels.

24138-83-8

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24138-83-8 Usage

Uses

Used in Pharmaceutical Industry:
5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione is used as an anti-hyperglycemic and anti-inflammatory medication for the treatment of type 2 diabetes. It enhances insulin sensitivity, leading to improved blood sugar control.
Used in Comprehensive Treatment Plans:
5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione is often prescribed in combination with other diabetes medications as part of a comprehensive treatment plan to manage type 2 diabetes effectively.

Check Digit Verification of cas no

The CAS Registry Mumber 24138-83-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,1,3 and 8 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 24138-83:
(7*2)+(6*4)+(5*1)+(4*3)+(3*8)+(2*8)+(1*3)=98
98 % 10 = 8
So 24138-83-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H6ClNO2S/c11-7-3-1-6(2-4-7)5-8-9(13)12-10(14)15-8/h1-5H,(H,12,13,14)

24138-83-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione

1.2 Other means of identification

Product number -
Other names (2E,4Z)-2,4-heptadienal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:24138-83-8 SDS

24138-83-8Relevant articles and documents

Design, synthesis, molecular docking, anticancer evaluations, and in silico pharmacokinetic studies of novel 5-[(4-chloro/2,4-dichloro)benzylidene]thiazolidine-2,4-dione derivatives as VEGFR-2 inhibitors

El-Adl, Khaled,El-Helby, Abdel-Ghany A.,Sakr, Helmy,Ayyad, Rezk R.,Mahdy, Hazem A.,Nasser, Mohamed,Abulkhair, Hamada S.,El-Hddad, Sanadelaslam S. A.

, (2020/10/20)

The anticancer activity of novel thiazolidine-2,4-diones was evaluated against HepG2, HCT-116, and MCF-7 cells. MCF-7 was the most sensitive cell line to the cytotoxicity of the new derivatives. In particular, compounds 18, 12, 17, and 16 were found to be the most potent derivatives over all the tested compounds against the cancer cell lines HepG2, HCT116, and MCF-7, with IC50 = 9.16 ± 0.9, 8.98 ± 0.7, 5.49 ± 0.5 μM; 9.19 ± 0.5, 8.40 ± 0.7, 6.10 ± 0.4 μM; 10.78 ± 1.2, 8.87 ± 1.5, 7.08 ± 1.6 μM; and 10.87 ± 0.8, 9.05 ± 0.7, 7.32 ± 0.4 μM, respectively. Compounds 18 and 12 have nearly the same activities as sorafenib (IC50 = 9.18 ± 0.6, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively), against HepG2 cells, but slightly lower activity against HCT116 cells and slightly higher activity against the MCF-7 cancer cell line. Also, these compounds displayed lower activities than doxorubicin against HepG2 and HCT-116 cells but higher activity against MCF-7 cells (IC50 = 7.94 ± 0.6, 8.07 ± 0.8, and 6.75 ± 0.4 μM, respectively). In contrast, compounds 17 and 16 exhibited lower activities than sorafenib against HepG2 and HCT116 cells, but nearly equipotent activity against the MCF-7 cancer cell line. Also, these compounds displayed lower activities than doxorubicin against the three cell lines. All the synthesized derivatives 7–18 were evaluated for their inhibitory activities against VEGFR-2. The tested compounds displayed high to medium inhibitory activity, with IC50 values ranging from 0.17 ± 0.02 to 0.27 ± 0.03 μM. Compounds 18, 12, 17, and 16 potently inhibited VEGFR-2 at IC50 values of 0.17 ± 0.02, 0.17 ± 0.02, 0.18 ± 0.02, and 0.18 ± 0.02 μM, respectively, which are nearly more than half of that of the IC50 value for sorafenib (0.10 ± 0.02 μM).

Permuted 2,4-thiazolidinedione (TZD) analogs as GLUT inhibitors and their in-vitro evaluation in leukemic cells

Aguilera, Renato J.,Choe, Jun-yong,Hess, Jessica D.,Iancu, Cristina V.,Macias, Lucasantiago Henze,Meyer-Almes, Franz-Josef,Mrowka, Piotr,Ramaa, C. S.,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha

, (2020/08/21)

Cancer is a heterogeneous disease, and its treatment requires the identification of new ways to thwart tumor cells. Amongst such emerging targets are glucose transporters (GLUTs, SLC2 family), which are overexpressed by almost all types of cancer cells; t

Synthesis and antimicrobial activity of a new series of thiazolidine-2,4-diones carboxamide and amino acid derivatives

Alhameed, Rakia Abd,Almarhoon, Zainab,Bukhari, Sarah I.,El-Faham, Ayman,De La Torre, Beatriz G.,Albericio, Fernando

, (2020/01/13)

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

A class of carbonic anhydrase IX/XII–selective carboxylate inhibitors

Alhameed, Rakia Abd,Almarhoon, Zainab,Berrino, Emanuela,El-Faham, Ayman,Supuran, Claudiu T.

, p. 549 - 554 (2020/02/13)

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.

Synthesis and anti-diabetic activity evaluation of phosphonates containing thiazolidinedione moiety

Sujatha, Bogiri,Chennamsetty, Subramanyam,Chintha, Venkataramaiah,Wudayagiri, Rajendra,Prasada Rao, Kammela

, p. 586 - 591 (2020/03/23)

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.

Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents

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)

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.

Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives

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)

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.

Biological evaluation of synthesised thiazolidinedione derivatives for anti-diabetic activity on STZ caused diabetes in rats

Geetha,Swarnalatha,Subba Reddy

, p. 1042 - 1048 (2019/06/28)

Diabetes Mellitus is the most common disease that poses a challenge to human health due to its secondary complications and resistance. Therefore, an attempt was made to synthesize novel compounds from thiazolidinedione moiety to treat the disease effectively and target diabetic complications. The synthesized compounds were tested for their physical parameters and characterised using NMR and IR spectra. They were also evaluated for STZ induced anti-diabetic activity in albino rats. The Compounds P5, II A8 and A9 were found effective in comparison with a standard drug, Pioglitazone. The other compounds were also effective but a reduction in activity is seen might be due to the inefficient binding to the PPAR receptors.

Anti-hepatitis-C virus activity and QSAR study of certain thiazolidinone and thiazolotriazine derivatives as potential NS5B polymerase inhibitors

Hassan, Ghaneya S.,Georgey, Hanan H.,Mohammed, Esraa Z.,Omar, Farghaly A.

, (2019/10/10)

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.

Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium

Gadekar, Sachin P.,Dipake, Sudarshan S.,Gaikwad, Suresh T.,Lande, Machhindra K.

, p. 7509 - 7518 (2018/09/06)

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.]

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