24138-83-8

Basic information

• Product Name: 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione
• Synonyms: 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione;5-(4-Chlorobenzylidene)-1,3-thiazolidine-2,4-dione;NSC 31152
• CAS NO: 24138-83-8
• Molecular Formula: C₁₀H₆ClNO₂S
• Molecular Weight: 239.68
• Mol File: 24138-83-8.mol
• Article Data: 30

Chemical Properties

• Melting Point: 230 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.527g/cm³
• Refractive Index: 1.707
• PKA: 7.16±0.20(Predicted)
• CAS DataBase Reference: 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione(24138-83-8)
• EPA Substance Registry System: 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione(24138-83-8)

Safety Data

• Hazardous Substances Data: 24138-83-8(Hazardous Substances Data)

Usage

General Description

5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione, also known as pioglitazone, is a chemical compound commonly used as a medication to treat type 2 diabetes. It belongs to the class of thiazolidinediones, which work by increasing the body's sensitivity to insulin, leading to improved control of blood sugar levels. Pioglitazone is known for its anti-hyperglycemic and anti-inflammatory properties. It is typically administered orally and is often prescribed in combination with other diabetes medications as part of a comprehensive treatment plan. Potential side effects of pioglitazone include weight gain, fluid retention, and an increased risk of bladder cancer. 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione is approved for use in several countries and has been the subject of ongoing research into its therapeutic effects and long-term safety profile.

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)

Upstream product

• 2295-31-0 thiazoline-2,4-dione 
• 104-88-1 4-chlorobenzaldehyde 
• 716336-73-1 1-benzylideneurea 
• 2362-79-0 N-(4-chlorobenzylidene)aniline 
• 36937-47-0 5-(4-Chlorophenylmethylene)-2-morpholino-4-oxo-2-thiazoline 
• 342379-47-9 (E,Z)-3-isopropyl-5-(4-chlorophenylmethylene)-1,3-thiazolidin-2,4-dione 
• 151-50-8 potassium cyanide 
• 461685-19-8 (E,Z)-3-allyl-5-(4-chlorophenylmethylene)-1,3-thiazolidin-2,4-dione 
• 76979-35-6 2-methylthio-5-p-chlorophenylmethylene-thiazolinone-4 
• 75-03-6 ethyl iodide 
• 71995-35-2 5-(4-Chlorophenylmethylene)-2,4-dioxothiazolidine potassium salt 

Downstream Products

• 51244-44-1 5-(4-chloro-benzylidene)-3-hydroxymethyl-thiazolidine-2,4-dione 
• 74942-60-2 6-(4-chlorobenzyl)-2-phenyl-3-phenylazo-1,2,4-triazin-5(2H)-one 
• 74942-59-9 3-(4-chlorophenyl)-N-(phenylhydrazinocarbonyl)-2-(phenylhydrazono)propanamide 
• 74942-54-4 3-(4-chlorophenyl)-N-(methylhydrazinocarbonyl)-2-(methylhydrazono)propanamide 
• 74942-53-3 6-(4-chlorobenzyl)-3-hydrazino-1,2,4-triazin-5(2H)-one 
• 74942-52-2 3-(4-chlorophenyl)-N-(hydrazinocarbonyl)-2-hydrazonopropanamide 
• 71995-35-2 5-(4-Chlorophenylmethylene)-2,4-dioxothiazolidine potassium salt 
• 40176-02-1 ethyl 2‐[5‐(4‐chlorobenzylidene)‐2,4‐dioxothiazolidin‐3‐yl]acetate 

Relevant articles and documents

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

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

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

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.