154592-60-6

Basic information

• Product Name: 1-fluoro-4-isoselenocyanatobenzene
• Synonyms: 1-fluoro-4-isoselenocyanatobenzene
• CAS NO: 154592-60-6
• Molecular Weight: 200.074
• Mol File: 154592-60-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1-fluoro-4-isoselenocyanatobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-fluoro-4-isoselenocyanatobenzene(154592-60-6)
• EPA Substance Registry System: 1-fluoro-4-isoselenocyanatobenzene(154592-60-6)

Safety Data

• Hazardous Substances Data: 154592-60-6(Hazardous Substances Data)

Upstream product

• 24075-34-1 4-fluorophenyl isocyanide 
• 64-18-6 formic acid 
• 371-40-4 4-fluoroaniline 
• 459-25-6 N-(4-fluorophenyl)formamide 

Downstream Products

• 154592-66-2 O-cyclododecyl-N-(4-fluorophenyl)selenocarbamate 
• 154592-72-0 N-(4-fluorophenyl)selenocarbamate of cholestanol 
• 1474041-91-2 1-(2-cyclohex-1-enylethyl)-3-(4-fluorophenyl)selenourea 
• 1474042-00-6 4-fluorophenyl(1-selena-3-azaspiro[5.5]undec-2-en-2-yl)amine hydrobromide 
• 315671-38-6 C₁₅H₁₉FN₂S 
• 1449684-50-7 N-(4-fluorophenyl)-5-{[(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)sulfanyl]methyl}-1,3,4-oxadiazol-2-amine 
• 1449684-38-1 2-[(1-benzyl-5-methyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-36-9 2-[(1,5-dimethyl-3-oxido-1H-imidazol-4-yl)carbonyl]-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-53-0 5-{[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]methyl}-2,4-dihydro-4-(4-methoxyphenyl)-3H-1,2,4-triazole-3-selone 
• 1449684-45-0 2-{[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]acetyl}-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-44-9 2-{[(1,5-dimethyl-4-phenyl-1H-imidazol-2-yl)sulfanyl]acetyl}-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-41-6 N-(4-fluorophenyl)-2-{[(1-methyl-4,5-diphenyl-1H-imidazol-2-yl)sulfanyl]acetyl}hydrazinecarboselenoamide 
• 1449684-54-1 4-(4-fluorophenyl)-2,4-dihydro-5-{[(1,4,5-trimethyl-1H-imidazol-2-yl)sulfanyl]methyl}-3H-1,2,4-triazole-3-selone 
• 1374039-16-3 N-(4'-fluorophenyl)(3-selena-1-azabicyclo[3.3.1]non-2-yliden)amine 

Relevant articles and documents

Novel 1,3,4-Selenadiazole-Containing Kidney-Type Glutaminase Inhibitors Showed Improved Cellular Uptake and Antitumor Activity

Kidney-type glutaminase [KGA/isoenzyme glutaminase C (GAC)] is becoming an important tumor metabolism target in cancer chemotherapy. Its allosteric inhibitor, CB839, showed early promise in cancer therapeutics but limited efficacy in in vivo cancer models. To improve the in vivo activity, we explored a bioisostere replacement of the sulfur atom in bis-2-(5-phenylacetamido-1,2,4-thiadiazol)ethyl sulfide and CB839 analogues with selenium using a novel synthesis of the selenadiazole moiety from carboxylic acids or nitriles. The resulting selenadiazole compounds showed enhanced KGA inhibition, more potent induction of reactive oxygen species, improved inhibition of cancer cells, and higher cellular and tumor accumulation than the corresponding sulfur-containing molecules. However, both CB839 and its selenium analogues show incomplete inhibition of the tested cancer cells, and a partial reduction in tumor size was observed in both the glutamine-dependent HCT116 and aggressive H22 liver cancer xenograft models. Despite this, tumor tissue damage and prolonged survival were observed in animals treated with the selenium analogue of CB839.

Synthesis of selenium analogues of 1-azabicyclo[4.4.0]decane

An approach to the synthesis of selenium bicyclic structures of the 1-azabicyclo[4.4.0]decane series was developed, which included the condensation of aryl isoselenocyanates with 2-(2-bromoethyl)piperidine and subsequent intramolecular cyclization of sele

Efficient synthesis of 4H-benzo[d][1,3]oxazin-4-ones from anthranilic acids and aryl isoselenocyanates

A synthesis in good to excellent yields of 23 4H-benzo[d][1,3]oxazin-4- ones, 18 of which are novel, from monosubstituted anthranilic acids and variously substituted phenyl isoselenocyanates without using any harsh reagents has been developed. The Se powder precipitated during the reaction could be efficiently recycled for the preparation of the aryl isoselenocyanates.