21494-64-4

Basic information

• Product Name: 3-butyl-2-thioxothiazolidin-4-one
• Synonyms: 3-butyl-2-thioxothiazolidin-4-one;3-butyl-2-sulfanylidene-1,3-thiazolidin-4-one;3-butyl-2-thioxo-1,3-thiazolidin-4-one;3-butyl-2-thioxo-4-thiazolidinone;3-Butylrhodanine;Rhodanine, 3-butyl-
• CAS NO: 21494-64-4
• Molecular Formula: C₇H₁₁NOS₂
• Molecular Weight: 189.29834
• EINECS: 244-408-9
• Mol File: 21494-64-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 264.4°Cat760mmHg
• Flash Point: 113.7°C
• Appearance: /
• Density: 1.27g/cm³
• Vapor Pressure: 0.0097mmHg at 25°C
• Refractive Index: 1.608
• PKA: -1.76±0.20(Predicted)
• CAS DataBase Reference: 3-butyl-2-thioxothiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-butyl-2-thioxothiazolidin-4-one(21494-64-4)
• EPA Substance Registry System: 3-butyl-2-thioxothiazolidin-4-one(21494-64-4)

Safety Data

• Hazardous Substances Data: 21494-64-4(Hazardous Substances Data)

Usage

General Description

3-butyl-2-thioxothiazolidin-4-one is a chemical compound that belongs to the thiazolidin-4-one family. It is a derivative of thiazolidine-2,4-dione and contains a butyl group attached to the third carbon atom. 3-butyl-2-thioxothiazolidin-4-one has potential biological activities and has been studied for its antiviral, antibacterial, and anti-inflammatory properties. Additionally, it has shown to have antioxidant and hepatoprotective effects. Its molecular structure makes it a promising candidate for pharmaceutical research and drug development.

InChI:InChI=1/C7H11NOS2/c1-2-3-4-8-6(9)5-11-7(8)10/h2-5H2,1H3

Upstream product

• 75-15-0 carbon disulfide 
• 105-39-5 chloroacetic acid ethyl ester 
• 109-73-9 N-butylamine 
• 3926-62-3 sodium monochloroacetic acid 
• 13558-70-8 methyl N-(chloroacetyl)carbamate 
• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 79-11-8 chloroacetic acid 

Downstream Products

• 93959-14-9 3-n-Butyl-5-(4-hydroxy-benzyliden)-4-oxo-thiazolidin-2-thion 
• 1204757-14-1 (Z)-5-(3-bromobenzylidene)-3-butyl-2-thioxothiazolidin-4-one 
• 64656-53-7 6-(3'-butyl-3-ethyl-4',4''-dioxo-4,5-diphenyl-2''-thioxo-3',4'-dihydro-3H-[2,5';2',5'']terthiazole-2(5'),2'(5'')-dien-3''-yl)-hexanoic acid isopropyl ester 
• 64896-07-7 3'-butyl-3-ethyl-2'-[2-(3-ethyl-4-oxo-2-thioxo-thiazolidin-5-ylidene)-ethylidene]-4,5-diphenyl-2',3'-dihydro-3H-[2,5']bithiazolyliden-4'-one 
• 93959-67-2 (E)-3-(4-Octyloxy-phenyl)-acrylic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-40-1 4-Decyloxy-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-39-8 4-Nonyloxy-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-38-7 4-Octyloxy-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-37-6 4-Heptyloxy-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-64-9 C₂₂H₂₄N₂O₂S₄ 
• 93959-32-1 4-Hexyloxy-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-26-3 4-Pentyloxy-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-50-3 4-((S)-2-Methyl-butoxy)-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 
• 93959-42-3 4-Heptyl-benzoic acid 4-[3-butyl-4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-phenyl ester 

Relevant articles and documents

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.

A concise approach to n-substituted rhodanines through a base-assisted one-pot coupling and cyclization process

An efficient approach to obtain functionalized rhodanines was developed through a base-assisted one-pot coupling and continuous cyclization of a primary amine, carbon disulfide, and methyl (2-chloroacetyl)carbamate. This conversion tolerates a broad range of functional groups and can be used to scale the preparation of N-substituted rhodanines in excellent yields.

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.