93103-15-2

Basic information

• Product Name: 1,3-dihydro-4-(4-fluorophenyl)-2h-imidazole-2-thione
• Synonyms: 1,3-dihydro-4-(4-fluorophenyl)-2h-imidazole-2-thion;1,3-dihydro-4-(4-fluorophenyl)-2h-imidazole-2-thione;4-(4-fluoro-phenyl)-1,3-dihydro-imidazole-2-thione
• CAS NO: 93103-15-2
• Molecular Formula: C₉H₇FN₂S
• Molecular Weight: 194.2286832
• Mol File: 93103-15-2.mol

Chemical Properties

• Boiling Point: 297.1°Cat760mmHg
• Flash Point: 133.5°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0.00138mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 1,3-dihydro-4-(4-fluorophenyl)-2h-imidazole-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dihydro-4-(4-fluorophenyl)-2h-imidazole-2-thione(93103-15-2)
• EPA Substance Registry System: 1,3-dihydro-4-(4-fluorophenyl)-2h-imidazole-2-thione(93103-15-2)

Safety Data

• Hazardous Substances Data: 93103-15-2(Hazardous Substances Data)

Usage

Chemical structure

Contains an imidazole ring and a thione functional group.

Potency

Potent inhibitor of monoamine oxidase-B (MAO-B).

Enzyme target

Inhibits the enzyme MAO-B, which breaks down certain neurotransmitters in the brain.

Research focus

Being researched for potential use in treating neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease.

Additional effects

Being studied for potential antidepressant and neuroprotective effects.

Research applications

Used in research settings to study the role of MAO-B in various physiological and pathological processes in the brain.

InChI:InChI=1/C9H7FN2S/c10-7-3-1-6(2-4-7)8-5-11-9(13)12-8/h1-5H,(H2,11,12,13)

Upstream product

• 89204-90-0 5-(4-Fluoro-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 333-20-0 potassium thioacyanate 
• 456-00-8 2-amino-4'-fluoroacetophenone hydrochloride 

Downstream Products

• 115859-13-7 1-methyl-2-(methylthio)-4-(4-fluorophenyl)-5-(1-carbethoxy-1,4-dihydro-4-pyridyl)imidazole 
• 115889-90-2 4-(4-fluorophenyl)-1-methyl-2-(methylsulfanyl)-1H-imidazole 

Relevant articles and documents

Structural Basis for EGFR Mutant Inhibition by Trisubstituted Imidazole Inhibitors

Acquired drug resistance in epidermal growth factor receptor (EGFR) mutant non-small-cell lung cancer is a persistent challenge in cancer therapy. Previous studies of trisubstituted imidazole inhibitors led to the serendipitous discovery of inhibitors that target the drug resistant EGFR(L858R/T790M/C797S) mutant with nanomolar potencies in a reversible binding mechanism. To dissect the molecular basis for their activity, we determined the binding modes of several trisubstituted imidazole inhibitors in complex with the EGFR kinase domain with X-ray crystallography. These structures reveal that the imidazole core acts as an H-bond acceptor for the catalytic lysine (K745) in the "αC-helix out" inactive state. Selective N-methylation of the H-bond accepting nitrogen ablates inhibitor potency, confirming the role of the K745 H-bond in potent, noncovalent inhibition of the C797S variant. Insights from these studies offer new strategies for developing next generation inhibitors targeting EGFR in non-small-cell lung cancer.

Synthetic and Mechanistic Studies on the Preparation of Pyridyl-Substituted Imidazothiazoles

A new method is presented for the introduction of the 4'-pyridyl substituent into 6-aryl-2,3-dihydroimidazothiazoles.The method involves treatment of the imidazothiazolines with the reactive complex of pyridine and ethyl chloroformate and oxidative deethyl carboxylation of the dihydropyridine adducts formed.Sulfur in refluxing mesitylene was found most suitable for the latter reaction, but chromium trioxide in pyridine or KtBuO and air were also effective.