24044-52-8

Basic information

• Product Name: 5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE
• Synonyms: AKOS BBS-00002497;5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE;5-[(3-Nitrophenyl)methylene]-1,3-thiazolidine-2,4-dione
• CAS NO: 24044-52-8
• Molecular Formula: C₁₀H₆N₂O₄S
• Molecular Weight: 250.23
• Mol File: 24044-52-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 185-187
• Appearance: /
• Density: 1.595 g/cm³
• Refractive Index: 1.732
• PKA: 7.14±0.20(Predicted)
• CAS DataBase Reference: 5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE(24044-52-8)
• EPA Substance Registry System: 5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE(24044-52-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 24044-52-8(Hazardous Substances Data)

Usage

General Description

5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE is a chemical compound with the molecular formula C10H6N2O4S. It is a thiazolidine-2,4-dione derivative that contains a nitrophenylmethylene group. 5-[(3-NITROPHENYL)METHYLENE]-1,3-THIAZOLANE-2,4-DIONE is often used in the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical structure and properties. It has been studied for its potential biological activities, including antimicrobial, anticancer, and antidiabetic properties. Additionally, it has been used as a building block for the development of new drug candidates and synthetic intermediates in organic chemistry.

InChI:InChI=1/C10H6N2O4S/c13-9-8(17-10(14)11-9)5-6-2-1-3-7(4-6)12(15)16/h1-5H,(H,11,13,14)/b8-5+

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 123043-88-9 5-ethoxycarbonyl-4-phenyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione 
• 79-11-8 chloroacetic acid 
• 292871-32-0 ethyl 5-phenyl-2-(3-nitrophenylmethylene)-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate 
• 63906-52-5 thiocyanatoacetic acid, Na-salt 
• 2295-31-0 thiazoline-2,4-dione 

Downstream Products

• 1235470-87-7 3-(2-biphenyl-4-yl-2-oxo-ethyl)-5-(3-nitro-benzylidene)-thiazolidine-2,4-dione 
• 16864-26-9 5-(3-nitro-benzylidene)-4-thioxo-thiazolidin-2-one 

Relevant articles and documents

Synthesis and characterization of pine-cone derived carbon-based solid acid: A green and recoverable catalyst for the synthesis of pyra-no_pyrazole, amino-benzochromene, amidoalkyl naphthol and thiazoli-dinedione derivatives

In this report, SO3H-functionalized Carbon nanoparticles (Pine-SO3H) with high acid density have been synthesized by the thermal treatment of sulfuric acid with Pine-Cone as carbon-based at 180oC in a sealed autoclave in a

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

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

Microwave assisted urea-acetic acid catalyzed knoevenagel condensation of ethyl cyanoacetate and 1,3-Thiazolidine-2,4-dione with aromatic aldehydes under solvent free condition

Knoevengel condensation reaction of various aromatic aldehydes with ethyl cyanoacetate and 1,3-thiazolidinone-2,4-diones catalyzed by urea-acetic acid under solvent free condition where olefinic products were obtained in high yield within short reaction time.