7648-01-3

Usage

Uses

Used in Solar and Photovoltaic Applications:
3-Ethylrhodanine is used as a donor in the development of efficient organic solar and photovoltaic cells. Its chemical properties make it a suitable candidate for enhancing the performance of these energy-harvesting devices, contributing to the advancement of renewable energy technologies.

InChI:InChI=1/C5H7NOS2/c1-2-6-4(7)3-9-5(6)8/h2-3H2,1H3

Upstream product

• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 75-04-7 ethylamine 
• 3926-62-3 sodium monochloroacetic acid 
• 75-15-0 carbon disulfide 
• 79-11-8 chloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 542-85-8 Ethyl isothiocyanate 
• 68-11-1 mercaptoacetic acid 
• 2950-35-8 5-(dimethylamino-methylene)-3-ethyl-2-thioxo-thiazolidin-4-one 

Downstream Products

• 10505-40-5 3-ethyl-5-[2-(3-ethyl-thiazolidin-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 107100-67-4 3-ethyl-2-thioxo-5-(3,5,5-trimethyl-cyclohex-2-enylidene)-thiazolidin-4-one 
• 112745-37-6 3-ethyl-5-((1Ξ)-11t-phenyl-undeca-2t,4t,6t,8t,10-pentaenylidene)-2-thioxo-thiazolidin-4-one 
• 124105-53-9 1,4-bis-[5-(3-ethyl-4-oxo-2-thioxo-thiazolidin-5-ylidene)-penta-1,3-dienyl]-benzene 
• 25962-08-7 3-ethyl-5-(1-ethyl-1H-pyridin-4-ylidene)-2-thioxo-thiazolidin-4-one 
• 23350-56-3 3-ethyl-5-[2-(1-ethyl-1H-quinolin-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 102025-38-7 3-ethyl-5-[(3-methyl-4-phenyl-3H-thiazol-2-yliden)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 25962-05-4 3-ethyl-5-[2-(3-ethyl-3H-benzooxazol-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 103154-18-3 3-ethyl-5-{[4-(4-methoxy-phenyl)-3-methyl-3H-thiazol-2-yliden]-ethylidene}-2-thioxo-thiazolidin-4-one 
• 115799-26-3 3-ethyl-5-{6-[4-(4-methoxy-phenyl)-3-methyl-3H-thiazol-2-ylidene]-hexa-2,4-dienylidene}-2-thioxo-thiazolidin-4-one 
• 100727-39-7 4-(3-ethyl-4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-benzaldehyde 
• 109725-20-4 3,3'-diethyl-2,2'-dithioxo-5,5'-p-phenylenedimethylene-bis-thiazolidin-4-one 
• 89411-09-6 3-ethyl-5-(4-nitro-benzylidene)-2-thioxo-thiazolidin-4-one 
• 41505-12-8 5-(3-anilino-allylidene)-3-ethyl-2-thioxo-thiazolidin-4-one 

Relevant academic research and scientific papers

5-Isopropylidene-3-ethyl rhodanine induce growth inhibition followed by apoptosis in leukemia cells

5-Isopropylidene-3-ethyl rhodanine II was prepared by conventional and Microwave assisted synthesis. For the first time, we found that rhodanine II treatment led to cytotoxicity in leukemic cell line, CEM by inducing apoptosis.

A facile one-pot, four-component synthesis of (Z)-isomer of rhodanine-oxindole derivatives under environmentally benevolent conditions

Herein, an efficient and sustainable one-pot, four-component access to rhodanine-oxindole derivatives is achieved by a reaction between primary amines, carbon disulfide, ethyl chloroacetate, and cyano-substituted alkenyl oxindoles. The reaction was conducted without any harsh conditions as well as exhausting workup in polyethylene glycol (PEG) as a green solvent at room temperature and delivered rhodanine-oxindole products in high yield. This publication is the first easy protocol to be reported for the rapid construction of new rhodanine-oxindole derivatives at room temperature without harsh conditions and via multicomponent reaction.

Unexpected Synthesis of 2,3,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence

Bis adducts derived from a double Michael addition of rhodanine to an azo-ene system of two molecules of 1,2-diaza-1,3-dienes (DDs) have furnished the corresponding 2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by means of a CS2 extrusion/double cyclization sequence. The incorporation of two units (4 and 2 atoms) of DDs into the fused bicyclic heterocycles represents a new application of this versatile class of molecules in heterocyclic synthesis.

Synthesis and evaluation of some novel N-substituted rhodanines for their anticancer activity

Novel N-substituted rhodanines 2a-g were synthesized by conventional and microwave-assisted methods and tested for their anticancer activity. Structure-activity relationship of the synthesized rhodanine 2a-g as antiproliferative agents was investigated. The results revealed that all the seven compounds showed potent antiproliferative activity in a concentration-dependent manner on leukemic cell line K562. Among the tested compounds, 2b was found to be more potent when compared by trypan blue and MTT assay. IC50 values of 2b using trypan blue and MTT assay were found to be 11.1 and 20.3 μg/ml, respectively. A dose-dependent increase in the LDH release was also observed upon treatment with 2a-g. Cell cycle analysis revealed that 2b affects DNA replication and leads to accumulation of cells in G0 and decline of G2/M, G1 and S phases which indicates apoptosis. The selective cytotoxic activity against human chronic myelogenous cell line (K562), via apoptosis, suggests that compound 2b is a promising scaffold for the development of novel anticancer drug.

Thiazolidinone-peptide hybrids as dengue virus protease inhibitors with antiviral activity in cell culture

The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

Aqueous microwave-assisted one-pot synthesis of N-substituted rhodanines

Two aqueous, one-pot, microwave-assisted methods for the rapid synthesis of N-substituted rhodanines from amine substrates are described. Alkyl- and benzylamines could be converted into the corresponding rhodanines with an atom-efficient one-pot, three-step protocol based on carbon disulfide and chloroacetic acid in short reaction times and good to excellent yields. An alternative, microwave-assisted one-pot, one-step protocol using bis(carboxymethyl)trithiocarbonate in water was developed for the synthesis of N-arylrhodanines from anilines.

USES AND COMPOSITIONS OF NITRATE ESTERS FOR PROVIDING SEDATION

Use of certain nitrate ester compounds or pharmaceutically acceptable salts thereof in the manufacture of a medicament for treating pain or providing analgesia.