4807-55-0

Basic information

• Product Name: 3-METHYLRHODANINE
• Synonyms: 3-Methyl-2-thioxo-1,3-thiazolidin-4-one;3-methyl-2-thioxo-4-thiazolidinon;3-Methylrhodanide;3-methyl-rhodanin;3-Methylrodanin;4-Thiazolidinone, 3-methyl-2-thioxo-;Methylrhodanine;n-methyl-rhodanin
• CAS NO: 4807-55-0
• Molecular Formula: C₄H₅NOS₂
• Molecular Weight: 147.22
• EINECS: 225-367-6
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Thiazoles;Building Blocks;C3 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 4807-55-0.mol

Chemical Properties

• Melting Point: 69-71 °C(lit.)
• Boiling Point: 213.4°C at 760 mmHg
• Flash Point: 82.9°C
• Appearance: /
• Density: 1.344 (estimate)
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.76±0.20(Predicted)
• CAS DataBase Reference: 3-METHYLRHODANINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLRHODANINE(4807-55-0)
• EPA Substance Registry System: 3-METHYLRHODANINE(4807-55-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-28-36/37/39-45
• WGK Germany: 3
• RTECS: VI8400000
• Hazardous Substances Data: 4807-55-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methylrhodanine is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs with therapeutic benefits.
Used in Cancer Research:
3-Methylrhodanine is utilized as an anti-cancer agent in research studies, exploring its effects on different types of cancer and its potential to be incorporated into cancer treatment protocols.
Used in Material Science:
In the field of material science, 3-Methylrhodanine is used as a building block in the synthesis of novel materials, owing to its unique chemical structure and properties.
Used in Health and Wellness Applications:
3-Methylrhodanine is considered for use in health and wellness products due to its antioxidant and radical scavenging properties, which may contribute to the prevention of oxidative stress-related conditions.

InChI:InChI=1/C4H5NOS2/c1-5-3(6)2-8-4(5)7/h2H2,1H3

Upstream product

• 68-11-1 mercaptoacetic acid 
• 556-61-6 methyl thioisocyanate 
• 186581-53-3 diazomethane 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 74-88-4 methyl iodide 
• 75-15-0 carbon disulfide 
• 3926-62-3 sodium monochloroacetic acid 
• 74-89-5 methylamine 
• 1068-52-6 sodium 2-bromoacetate 
• 593-51-1 methylamine hydrochloride 
• 63906-52-5 thiocyanatoacetic acid, Na-salt 
• 79-11-8 chloroacetic acid 
• 13558-70-8 methyl N-(chloroacetyl)carbamate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 86291-07-8 (3-methyl-4-oxo-2-thioxo-thiazolidin-5-yl)-(4-oxo-3-phenyl-2-thioxo-thiazolidin-5-ylidene)-methane 
• 113059-39-5 3-methyl-5-[2-(1-methyl-1H-[2]quinolylidene)-1-phenyl-ethylidene]-2-thioxo-thiazolidin-4-one 
• 108247-74-1 3-methyl-5-[2-(1-methyl-6-phenylethynyl-1H-[2]pyridylidene)-1-phenyl-ethylidene]-2-thioxo-thiazolidin-4-one 
• 23517-83-1 5-(4-chlorophenylmethylene)-3-methyl-4-oxo-2-thioxothiazolidine 
• 5178-04-1 3-methyl-5-benzylidenerhodanine 
• 99970-22-6 2-(3-methyl-4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-benzoic acid 
• 5199-12-2 2-Thioxo-3-methyl-4-oxo-5-piperidinomethylen-thiazolidin 
• 5199-18-8 5-[3-(4-methoxy-phenyl)-allylidene]-3-methyl-2-thioxo-dihydro-thiazolidin-4-one 
• 106595-96-4 5-(5-anilino-penta-2,4-dienylidene)-3-methyl-2-thioxo-thiazolidin-4-one 
• 51039-39-5 3-methyl-5-(9-phenyl-9H-dibenzo[a,c]phenazin-11-ylidene)-2-thioxo-thiazolidin-4-one 
• 34709-43-8 3-methyl-5-(4-methyl-benzylidene)-2-thioxo-thiazolidin-4-one 
• 33366-50-6 3-Methyl-5-<(1-naphthyl)methylen>rhodanin 
• 28996-47-6 3-methyl-5-(4-nitro-benzylidene)-2-thioxo-thiazolidin-4-one 
• 49661-67-8 3-benzyl-3'-methyl-2'-thioxo-tetrahydro-[2,5']bithiazolyliden-4'-one 

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 New Synthesis Strategy for Rhodanine and Its Derivatives

Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N -aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid, which provides a new approach of the synthesis of rhodanine and its derivatives. The developed strategy is straightforward, efficient, atom economical, and convenient in good yields.

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.

Diversity-Oriented Approach to Spirorhodanines via a [2+2+2] Cyclotrimerization

Spirocyclic compounds have been increasingly utilized in drug discovery due to their inherent three-dimensional structural complexity. Here, we report a diversity oriented approach to spirorhodanines via a [2+2+2] cyclotrimerization reaction with propargyl halides as co-partners. In another sequence, we employed o-xylylene dibromide as a coupling partner to assemble spirorhodanines.

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.

Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors

We have previously reported the discovery of a new class of potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) derived from benzylidene oxazolidinedione and thiazolidinedione scaffolds. In this study, these analogs were designed, synthesized, and evaluated in a human cell-based assay. The detailed structure-activity relationship (SAR) surrounding this pharmacophore were developed, and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg, 16 showed approximately two times more potent testosterone (T)-lowering effect against a positive control in the luteinizing hormone-releasing hormone (LH-RH)-induced T production assay. The T-lowering effect continued at ca 10% level of control over 4 h after administration. The nonsteroidal molecules based on this series have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer.

An expeditious, environment-friendly, and microwave-assisted synthesis of 5-isatinylidenerhodanine derivatives

A series of nine 5-arylidenerhodanine derivatives was prepared in good yields and purity without the use of a solvent or catalyst under microwave-assisted condensation with some substituted isatins. All 5-arylidenerhodanines were evaluated as possible inhibitors of the CK1α/β, CDK5/p25, and GSK-3α/β kinases. None of them showed substantive inhibitory activity against these kinases when evaluated at the concentration of 10 μM.

A Versatile and Practical Synthesis toward the Development of Novel HIV-1 Integrase Inhibitors

As a continuation of our previous work, which resulted in the identification of a new hit compound as an HIV-1 integrase inhibitor, three novel series of salicylic acid derivatives were synthesized using three versatile and practical synthetic strategies and were assayed for their capacity to inhibit the catalytic activity of HIV-1 integrase. Biological evaluations revealed that some of the synthesized compounds possess good inhibitory potency in enzymatic assays and are able to inhibit viral replication in MT-4 cells at low micromolar concentrations. Finally, docking studies were conducted to analyze the binding mode of the synthesized compounds within the DNA binding site of integrase in order to refine their structure-activity relationships. Easy as A, B, C: Three new series of salicylic acid derivatives were designed and synthesized to investigate their activity toward HIV-1 integrase. Some of these compounds were obtained with microwave-assisted procedures developed and optimized in our research group, which allowed us to rapidly generate several final compounds of high purity.

Synthesis of new rhodacyanines analogous to MKT-077 under microwave irradiation

We report here a synthesis of a new rhodacyanines 7X analogous to MKT-077 with quantitative yield using as starting material the thiazolinethione 1. Merocyanines 4 and their tosylates 5 have been prepared as intermediates for this class of compounds. The reactions leading to rhodacyanine 7X have been studied under microwave irradiation. Copyright Taylor & Francis Group, LLC.