3460-49-9

Usage

Uses

Used in Organic Synthesis:
4-Ethoxyphenyl isothiocyanate is used as a reagent in organic synthesis for the purpose of introducing the isothiocyanate functional group into target molecules, which is crucial for the development of various chemical compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 4-ethoxyphenyl isothiocyanate is used as a building block for the creation of new drugs, leveraging its chemical properties to enhance the therapeutic potential of medications.
Used in Agrochemical Production:
4-ETHOXYPHENYL ISOTHIOCYANATE is also utilized in the agrochemical sector, where it serves as a key component in the synthesis of pesticides and other agricultural chemicals to protect crops and enhance yield.
Used in Specialty Chemicals:
4-Ethoxyphenyl isothiocyanate finds application in the production of specialty chemicals, where its unique properties contribute to the development of niche products with specific applications.
Used in Anticancer Research:
4-Ethoxyphenyl isothiocyanate is studied for its potential anticancer properties, exploring its ability to inhibit the growth of cancer cells and its potential integration into cancer treatment protocols.
Used in Enzyme Inhibition Studies:
4-ETHOXYPHENYL ISOTHIOCYANATE is also researched for its capacity to inhibit various enzymes, which can be significant in understanding and potentially treating enzyme-related diseases and conditions.

InChI:InChI=1/C9H9NOS/c1-2-11-9-5-3-8(4-6-9)10-7-12/h3-6H,2H2,1H3

Upstream product

• 87551-32-4 (4-ethoxy-phenyl)-dithiocarbamic acid 
• 594-42-3 chlorothio-trichloro-methane 
• 156-43-4 4-Ethoxyaniline 
• 463-71-8 thiophosgene 
• 1234-30-6 N,N'-bis-(4-ethoxy-phenyl)-thiourea 
• 67-56-1 methanol 
• 39680-72-3 3-(4-ethoxy-phenyl)-2-thioxo-[1,3]thiazinan-4-one 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 75-15-0 carbon disulfide 

Downstream Products

• 108483-67-6 azetidine-1-carbothioic acid 4-ethoxy-anilide 
• 101274-35-5 3-(4-ethoxy-phenyl)-5-furfurylidene-2-thioxo-thiazolidin-4-one 
• 893-59-4 N-(4-ethoxyphenyl)-N'-(2-pyridyl) thiourea 
• 100973-55-5 N-(4-ethoxy-phenyl)-N'-(5-methyl-[2]pyridyl)-thiourea 
• 100720-16-9 N-(4-ethoxy-phenyl)-N'-(3,4-dimethyl-isoxazol-5-yl)-thiourea 
• 109403-46-5 4-(4-ethoxy-phenyl)-1-nicotinoyl thiosemicarbazide 
• 26416-42-2 4-(4-ethoxyphenyl)-1-(isonicotinoyl)thiosemicarbazide 
• 111065-56-6 N-(4-ethoxy-phenyl)-N'-(4-[4]pyridyl-phenyl)-thiourea 
• 102082-09-7 N-(4-ethoxy-phenyl)-N'-(4-amino-2-methyl-[6]quinolyl)-thiourea 
• 112351-79-8 N-(4-ethoxy-phenyl)-N'-dibenzofuran-3-yl-thiourea 
• 102240-61-9 N-(4-ethoxy-phenyl)-N'-(4-piperidino-phenyl)-thiourea 
• 42974-24-3 4-(4-ethoxy-phenyl)-1-(benzofuran-2-carbonyl)-thiosemicarbazide 
• 102158-01-0 N-(4-ethoxy-phenyl)-N'-(4-[2]pyridylsulfamoyl-phenyl)-thiourea 
• 102028-36-4 3-(4-ethoxy-phenyl)-5-benzylidene-2-thioxo-thiazolidin-4-one 

Relevant academic research and scientific papers

NaOH-promoted one-pot aryl isothiocyanate synthesis under mild benchtop conditions

In this work, we have established a green synthesis of aryl isothiocyanates promoted by the low-cost and readily available NaOH from aryl amines and carbon disulfide in a one-pot procedure. The developed protocol features no extra desulfurating reagents and mild benchtop conditions, in which NaOH serves as both the base and the desulfurating reagent to decompose the dithiocarbamate intermediate. Fourteen examples of aryl amines bearing electronic neutral, rich and poor substituents, as well as benzylamine, have proved to be compatible substrates in the developed method to furnish the corresponding isothiocyanates. The reaction has been performed on a gram scale to further demonstrate its synthetic utility. Compared to the reported base-promoted synthesis of aryl isothiocyanates that requires the use of special equipment, such as the ball mill or the microwave reactor, the simplicity in operation and scalability enables this method to efficiently access a variety of aryl isothiocyanates.

Structure-Activity Relationships and Computational Investigations into the Development of Potent and Balanced Dual-Acting Butyrylcholinesterase Inhibitors and Human Cannabinoid Receptor 2 Ligands with Pro-Cognitive in Vivo Profiles

The enzyme butyrylcholinesterase (BChE) and the human cannabinoid receptor 2 (hCB2R) represent promising targets for pharmacotherapy in the later stages of Alzheimer's disease. We merged pharmacophores for both targets into small benzimidazole-based molecules, investigated SARs, and identified several dual-acting ligands with a balanced affinity/inhibitory activity and an excellent selectivity over both hCB1R and hAChE. A homology model for the hCB2R was developed based on the hCB1R crystal structure and used for molecular dynamics studies to investigate binding modes. In vitro studies proved hCB2R agonism. Unwanted μ-opioid receptor affinity could be designed out. One well-balanced dual-acting and selective hBChE inhibitor/hCB2R agonist showed superior in vivo activity over the lead CB2 agonist with regards to cognition improvement. The data shows the possibility to combine a small molecule with selective and balanced GPCR-activity/enzyme inhibition and in vivo activity for the therapy of AD and may help to rationalize the development of other dual-acting ligands.

Aminobenzimidazoles and Structural Isomers as Templates for Dual-Acting Butyrylcholinesterase Inhibitors and hCB2R Ligands To Combat Neurodegenerative Disorders

A pharmacophore model for butyrylcholinesterase (BChE) inhibitors was applied to a human cannabinoid subtype 2 receptor (hCB2R) agonist and verified it as a first-generation lead for respective dual-acting compounds. The design, synthesis, and pharmacological evaluation of various derivatives led to the identification of aminobenzimidazoles as second-generation leads with micro- or sub-micromolar activities at both targets and excellent selectivity over hCB1and AChE, respectively. Computational studies of the first- and second-generation lead structures by applying molecular dynamics (MD) on the active hCB2R model, along with docking and MD on hBChE, has enabled an explanation of their binding profiles at the protein levels and opened the way for further optimization. Dual-acting compounds with “balanced” affinities and excellent selectivities could be obtained that represent leads for treatment of both cognitive and pathophysiological impairment occurring in neurodegenerative disorders.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

Experimental and Theoretical Studies of Substituent Effects in Hydrogen Bond Based Molecular Recognition of a Zwitterion by Substituted Arylureas

Electron withdrawing groups have a strong effect on hydrogen bonding to aryl ureas.The effect of para substituents modestly exceeds the effect of meta substituents.Among common substituent parameters, ?- (ρ = 1.77, r2 = 0.988) is found to be the best predictor for the observed effects of para substituents in aryl ureas.Semi-empirical and ab initio methods are used to calculate charge distributions in substituted benzene derivatives and in these ureas.A comparison of experimental and predicted (AM1, STO3G, 321-G*, 631-G**) dipole moments of benzene derivatives is presented.It is shown that calculated surface electric potentials for these thioureas succesfully predict the relative hydrogen bonded association energies.