10574-69-3

Usage

Uses

Used in Pharmaceutical Industry:
3-BENZYLRHODANINE is used as a pharmaceutical intermediate for its potential therapeutic applications. Its biological activities, such as anticancer properties, make it a candidate for the development of new drugs targeting various types of cancer.
Used in Agrochemical Industry:
3-BENZYLRHODANINE is used as an active ingredient in agrochemicals for its antibacterial and antifungal properties. It can be incorporated into products designed to protect crops from diseases and pests, thereby enhancing agricultural productivity.
Used in Materials Science:
3-BENZYLRHODANINE is used as a building block in materials science for the synthesis of new materials with specific properties. Its reactivity and structural features allow for the creation of compounds that can be applied in various material technologies, such as sensors, catalysts, or advanced materials with unique characteristics.
Research on 3-BENZYLRHODANINE continues to explore its potential as a versatile and valuable chemical entity, with ongoing studies aiming to unlock further applications and optimize its use in different industries.

InChI:InChI=1/C10H9NOS2/c12-9-7-14-10(13)11(9)6-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 6326-83-6 bis(carboxymethyl)trithiocarbonate 
• 100-46-9 benzylamine 
• 105-39-5 chloroacetic acid ethyl ester 
• 3926-62-3 sodium monochloroacetic acid 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 41270-27-3 N-benzyl-dithiocarbamic acid ammonium salt 
• 79-11-8 chloroacetic acid 
• 75-15-0 carbon disulfide 
• 79-08-3 bromoacetic acid 
• 105-36-2 ethyl bromoacetate 
• 623-51-8 ethyl 2-sulfanylacetate 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 622-78-6 Benzyl isothiocyanate 

Downstream Products

• 691881-38-6 (5E)-3-benzyl-2-thioxo-5-({5-[3-(trifluoromethyl)phenyl]-2-furyl}methylene)-1,3-thiazolidin-4-one 
• 691881-40-0 (5Z)-3-benzyl-5-{[5-(2-trifluoromethylphenyl)-2-furyl]methylene}-2-thioxo-1,3-thiazolidin-4-one 
• 691881-39-7 (5Z)-3-benzyl-5-{[5-(4-trifluoromethylphenyl)-2-furyl]methylene}-2-thioxo-1,3-thiazolidin-4-one 
• 1204757-13-0 (Z)-5-(3-bromobenzylidene)-3-benzyl-2-thioxothiazolidin-4-one 
• 1403891-66-6 C₁₉H₁₃FN₂O₂S₂ 
• 375353-33-6 C₁₉H₁₄N₂O₃S₂ 

Relevant academic research and scientific papers

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.

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.

IDO inhibitors

Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

HETEROCYCLIC INTEGRIN AGONISTS

The present invention provides polycyclic oxothioxoimidazolidines, dioxoimidazolines, oxothioxooxazolidines, dioxooxazolidines, and related compounds, which are useful as integrin agonists. Methods for the treatment of integrin-mediated diseases such as cancer are also described.

Novel rhodanines with anticancer activity: Design, synthesis and CoMSIA study

Three different series of some novel N-substituted rhodanines were designed for anticancer activity and prepared from the corresponding dithiocarbamates. The synthesized compounds were analyzed by IR, NMR and MASS to confirm their structures. All the titl

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.

Small molecule fusion inhibitors: Design, synthesis and biological evaluation of (Z)-3-(5-(3-benzyl-4-oxo-2-thioxothiazolidinylidene)methyl)-N-(3- carboxy-4-hydroxy)phenyl-2,5-dimethylpyrroles and related derivatives targeting HIV-1 gp41

By a scaffold elongation strategy, a series of (Z)-3-(5-(3-benzyl-4-oxo-2- thioxothiazolidinylidene)methyl)-N-(3-carboxy-4-hydroxy)phenyl-2, 5-dimethylpyrroles and related derivatives with a linear multi-aromatic-ring skeleton were designed, synthesized, and evaluated in HIV-1 gp41 and cellular assays. Among them, the most active compounds, 12e, 12g, and 12k with a one-carbon linker (n = 1) between the rhodanine (C) and phenyl (D) rings, exhibited very promising inhibitory potency with IC50 values of 1.8-2.6 μM and EC50 values of 0.3-1.5 μM against gp41 6-HB formation and HIV-1 replication in MT-2 cells, respectively. Additionally, they were almost equally effective against both T20-sensitive and resistant strains. The related SAR studies and molecular modeling results provided potential for further developing a new class of non-peptide small molecular fusion inhibitors targeting the HIV-1 gp41.

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.

Design, synthesis and biological evaluation of 3-substituted 2,5-dimethyl-N-(3-(1H-tetrazol-5-yl)phenyl)pyrroles as novel potential HIV-1 gp41 inhibitors

Based on the structure of HIV-1 gp41 binding site for small-molecule inhibitors, optimization of lead 2 resulted in the discovery of a new series of 2,5-dimethyl-3-(5-(N-phenylrhodaninyl)methylene)-N-(3-(1H-tetrazol-5-yl)phenyl) pyrrole compounds with improved anti-HIV-1 activity. The most active compounds 13a and 13j exhibited significant potency against gp41 6-HB formation with IC50 values of 4.4 and 4.6 μM and against HIV-1 replication in the MT-2 cells with EC50 values of 3.2 and 2.2 μM, respectively, thus providing a new starting point to develop highly potent small-molecule HIV fusion inhibitors targeting gp41.

Electrogenerated base-promoted synthesis of N-benzylic rhodanine and carbamodithioate derivatives

Electrogenerated magnesium-associated cyanomethyl anions/bases obtained from the electrochemical reduction of acetonitrile and the oxidation of a sacrificial magnesium rod were successfully used to promote the addition of carbon disulfide to primary benzylic amines. Alkylation with ethyl 3-bromopropionate acid ester or with ethyl 2-bromoacetate acid ester yields the corresponding ring-opened carbamodithioate compounds or cyclic rhodanine derivatives, respectively. The effect of the amount of electrogenerated base on the yield of reaction was also evaluated.