7025-19-6

Basic information

• Product Name: N-CARBOXYETHYLRHODANINE
• Synonyms: 3-Thiazolidinepropanoic acid, 4-oxo-2-thioxo-;3-Thiazolidinepropionic acid, 4-oxo-2-thioxo-;4-oxo-2-thioxo-3-thiazolidinepropionicaci;Rodanin-3-propionic acid;rodanin-3-propionicacid;AKOS BBS-00002147;3-(4-OXO-2-THIOXO-1,3-THIAZOLIDIN-3-YL)PROPANOIC ACID;3-(4-OXO-2-THIOXO-THIAZOLIDIN-3-YL)-PROPIONIC ACID
• CAS NO: 7025-19-6
• Molecular Formula: C₆H₇NO₃S₂
• Molecular Weight: 205.25
• EINECS: 230-307-7
• Mol File: 7025-19-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 158-160°C
• Boiling Point: 385.9 °C at 760 mmHg
• Flash Point: 187.2 °C
• Appearance: /
• Density: 1.61 g/cm³
• Vapor Pressure: 1.86E-06mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.36±0.10(Predicted)
• CAS DataBase Reference: N-CARBOXYETHYLRHODANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-CARBOXYETHYLRHODANINE(7025-19-6)
• EPA Substance Registry System: N-CARBOXYETHYLRHODANINE(7025-19-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: XJ6094060
• HazardClass: IRRITANT
• Hazardous Substances Data: 7025-19-6(Hazardous Substances Data)

Usage

General Description

N-CARBOXYETHYLRHODANINE, also known as 4-CARBOXYETHYLRHODANINE, is a chemical compound that belongs to the class of rhodanine derivatives. It is commonly used as a fluorescent dye in biological and medical research, particularly in imaging applications. Its unique spectral properties, including high quantum yield and photostability, make it a valuable tool for visualizing and tracking biological molecules and processes. N-CARBOXYETHYLRHODANINE is known for its bright red fluorescence and has been utilized in a variety of bioimaging techniques, such as confocal microscopy, flow cytometry, and fluorescence resonance energy transfer (FRET) assays. Additionally, it can be modified with different functional groups to tailor its properties for specific applications, making it a versatile tool in the field of biological imaging.

InChI:InChI=1/C6H7NO3S2/c1-3(5(9)10)7-4(8)2-12-6(7)11/h3H,2H2,1H3,(H,9,10)

Upstream product

• 75-15-0 carbon disulfide 
• 1068-52-6 sodium 2-bromoacetate 
• 107-95-9 3-amino propanoic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 7748-25-6 potassium chloroacetate 
• 79-08-3 bromoacetic acid 
• 79-11-8 chloroacetic acid 

Downstream Products

• 7177-97-1 3-[5-(4-chloro-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid 
• 7025-23-2 3-[5-(4-nitro-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid 
• 7110-79-4 NL-16 
• 7025-21-0 3-[5-(2-hydroxy-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-propionic acid 
• 7025-17-4 3-[4-oxo-5-(3-phenyl-allylidene)-2-thioxo-thiazolidin-3-yl]-propionic acid 
• 19375-21-4 3-(4-oxo-2-thioxo-thiazolidin-3-yl)-propionic acid benzyl ester 
• 1279692-51-1 N-(2-nitrophenyl)-3-(4-oxo-2-thioxothiazolidin-3-yl)propanamide 
• 1279692-50-0 N-(2-hydroxyphenyl)-3-(4-oxo-2-thioxothiazolidin-3-yl)propanamide 
• 1279692-24-8 3-[(Z)-5-(3-fluorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-N-(2-hydroxyphenyl)propanamide 
• 1279692-25-9 3-[(Z)-5-(3,5-difluorobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-N-(2-hydroxyphenyl)propanamide 
• 1279692-26-0 3-[(Z)-5-(3-methylbenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-N-(2-hydroxyphenyl)propanamide 
• 1279692-27-1 3-[(Z)-5-(3-methoxylbenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-N-(2-hydroxyphenyl)propanamide 
• 1279692-28-2 3-{(Z)-5-[(benzo[d][1,3]dioxol-5-yl)methylene]-4-oxo-2-thioxothiazolidin-3-yl}-N-(2-hydroxyphenyl)propanamide 
• 1279692-29-3 3-[(Z)-5-(3-bromobenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]-N-(2-nitrophenyl)propanamide 

Relevant articles and documents

Structure-guided design of thiazolidine derivatives as mycobacterium tuberculosis pantothenate synthetase inhibitors

The pantothenate biosynthetic pathway is essential for the persistent growth and virulence of Mycobacterium tuberculosis (Mtb) and one of the enzymes in the pathway, pantothenate synthetase (PS, EC: 6.3.2.1), encoded by the panC gene, has become an appropriate target for new therapeutics to treat tuberculosis. Herein, we report nanomolar thiazolidine inhibitors of Mtb PS developed by a rational inhibitor design approach. The thiazolidine compounds were discovered by using energy-based pharmacophore modelling and subsequent in vitro screening, which resulted in compounds with a half maximal inhibitory concentration (IC50) value of (1.12±0.12) μM. These compounds were subsequently optimised by a combination of modelling and synthetic chemistry. Hit expansion of the lead by chemical synthesis led to an improved inhibitor with an IC50 value of 350 nM and an Mtb minimum inhibitory concentration (MIC) of 1.55 μM. Some of these compounds also showed good activity against dormant Mtb cells. Let sleeping cells lie: Mycobacterium tuberculosis pantothenate synthetase (Mtb PS) has become a target for new therapeutics to treat tuberculosis. Nanomolar thiazolidine inhibitors of Mtb PS were developed by rational inhibitor design involving modelling, in vitro screening and optimisation. Hit expansion of the lead by synthesis led to an improved inhibitor with an IC50 value of 350 nM and an Mtb MIC value of 1.55 μM. Some of these compounds also showed good activity against dormant Mtb cells.

5-(1H-Indol-3-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)alkancarboxylic Acids as Antimicrobial Agents: Synthesis, biological evaluation, and molecular docking studies

Background: Infectious diseases symbolize a global consequential strain on public health security and impact on the socio-economic stability all over the world. The increasing resistance to the current antimicrobial treatment has resulted in crucial need for the discovery and development of novel entity for the infectious treatment with different modes of action that could target both sensitive and resistant strains. Methods: Compounds were synthesized using classical methods of organic synthesis. Results: All 20 synthesized compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species. It should be mentioned that all compounds exhibited better antibacterial potency than ampicillin against all bacteria tested. Furthermore, 18 compounds appeared to be more potent than streptomycin against Staphylococcus aureus, Enterobacter cloacae, Pseudomonas aeruginosa, Listeria monocytogenes, and Escherichia coli. Three the most active compounds 4h, 5b, and 5g appeared to be more potent against MRSA than ampicillin, while streptomycin did not show any bactericidal activity. All three compounds displayed better activity also against resistant strains P. aeruginosa and E. coli than ampicillin. Furthermore, all compounds were able to inhibit biofilm formation 2- to 4-times more than both reference drugs. Compounds were evaluated also for their antifungal activity against eight species. The evaluation revealed that all compounds exhibited antifungal activity better than the reference drugs bifonazole and ketoconazole. Molecular docking studies on antibacterial and antifungal targets were performed in order to elucidate the mechanism of antibacterial activity of synthesized compounds. Conclusion: All tested compounds showed good antibacterial and antifungal activity better than that of reference drugs and three the most active compounds could consider as lead compounds for the development of new more potent agents.

Antibacterial properties of 5-substituted derivatives of rhodanine-3-carboxyalkyl acids

A series of rhodanine 3-carboxyalkanoic acid derivatives possessing 4′-(N,N-dialkyl-amino or diphenylamino)-benzylidene moiety as a substituent at the C-5 position were synthesised and their antibacterial activity was screened. All the rhodanine derivatives showed bacteriostatic or bactericidal activity to the reference gram-positive bacterial strains, but lack of activity to the reference Gram-negative bacterial strains and yeast strains was observed.