147695-56-5

Basic information

• Product Name: 4-bromophenyl isoselenocyanate
• Synonyms: 4-bromophenyl isoselenocyanate
• CAS NO: 147695-56-5
• Molecular Weight: 260.979
• Mol File: 147695-56-5.mol

Chemical Properties

• CAS DataBase Reference: 4-bromophenyl isoselenocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromophenyl isoselenocyanate(147695-56-5)
• EPA Substance Registry System: 4-bromophenyl isoselenocyanate(147695-56-5)

Safety Data

• Hazardous Substances Data: 147695-56-5(Hazardous Substances Data)

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 106-40-1 4-bromo-aniline 
• 33554-73-3 1-bromo-4-isocyanobenzene 
• 64-18-6 formic acid 
• 2617-78-9 N-(4-bromophenyl)formamide 

Downstream Products

• 685901-65-9 3-acetyl-N-(4-bromophenyl)-4-diethylaminoselenet-2(2H)-imine 
• 1453815-66-1 1-(4-bromophenyl)-5-[(3,5-dinitrobenzyl)selanyl]-1H-tetrazole 
• 1453815-67-2 N-(4-Bromphenyl)-N-(3,5-dinitrobenzyl)cyanamide 
• 1453815-68-3 (Z)-Se-(3,5-dinitrobenzyl)-N-cyano-N,N'-di(4-bromophenyl)isoselenourea 
• 66497-35-6 N,N'-bis-(4-bromophenyl)selenourea 
• 1226911-95-0 N-(4-bromophenyl)-N'-[4-(dimethylamino)phenyl]selenourea 
• 1226911-94-9 N-(4-bromophenyl)-N'-(4-methoxyphenyl)selenourea 
• 1226911-96-1 N-(4-bromophenyl)-N'-(4-methylphenyl)selenourea 
• 880384-20-3 tert-butyl 3-tert-butoxy-4-(4-bromophenyl)-4,5-dihydro-5-selenoxo-1H-1,2,4-triazole-1-carboxylate 

Relevant articles and documents

Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors

A series of benzenesulfonamides bearing selenourea moieties was obtained considering the ureido-sulfonamide SLC-0111, in Phase I clinical trials as antitumor agent, as a lead molecule. All compounds showed interesting inhibition potencies against the physiologically relevant human (h) carbonic anhydrase (hCAs, EC 4.2.1.1) isoforms I, II, IV, and IX. The most flexible analogues in the series 14-19 showed low nanomolar inhibition constants against hCA I, II, and IX. We assessed selected compounds on the in vitro antioxidant properties and binding modes and evaluated ex vivo human prostate (PC3), breast (MDA-MB-231), and colon-rectal (HT-29) cancer cell lines both in normoxic and hypoxic conditions.

Selenoureido-iminosugars: A new family of multitarget drugs

Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for tackling simultaneously the Gaucher disease (by selective inhibition of β-glucosidase, Ki= 1.6–5.5 μM, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, Kiup to 5.8 μM). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2(Kcat/Kuncatup to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)2and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders.

1-Substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their isosteric analogs: A new class of selective antitubercular agents active against drug-susceptible and multidrug-resistant mycobacteria

In this work, a new class of highly potent antituberculosis agents, 1-substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their oxa and selanyl analogs, is described. The minimal inhibitory concentration (MIC) values reached 1 μM (0.36-0.44 μg/mL) against Mycobacterium tuberculosis CNCTC My 331/88 and 0.25-1 μM against six multidrug-resistant clinically isolated strains of M. tuberculosis. The antimycobacterial effects of these compounds were highly specific because they were ineffective against all eight bacterial strains and eight fungal strains studied. Furthermore, these compounds exhibited low in vitro toxicity in four mammalian cell lines (IC50 > 30 μM). We also examined the structure-activity relationships of the compounds, particularly the effects on antimycobacterial activity of the number and position of the nitro groups, the linker between tetrazole and benzyl moieties, and the tetrazole itself. Relatively high variability of substituent R 1 on the tetrazole in the absence of negative effects on antimycobacterial activity allows further structural optimization with respect to toxicity and the ADME properties of the 1-substituted-5-[(3,5-dinitrobenzyl) sulfanyl]-1H-tetrazoles lead compounds.

One-pot synthesis of 1-substituted-5-alkylselanyl-1H-tetrazoles from isoselenocyanates: Unexpected formation of N-alkyl-N-arylcyanamides and (Z)-Se-alkyl-N-cyano-N,N′-diarylisoselenoureas

1-Substituted-5-alkylsulfanyl-1H-tetrazoles are well known class of organic substances with various applications in medicinal chemistry or photographic industry. Their selenium analogues, 1-substituted-5-alkylselanyl-1H-tetrazoles are, however, much less explored because of the lack of suitable methods for their preparation. In this work we investigated the synthesis of 1-alkyl/aryl-5-alkylselanyl-1H-tetrazoles from synthetically available alkyl/arylisoselenocyanates. One-pot reactions of arylisoselenocyanates with sodium azide and alkylating agent led to the target 5-alkylselanyl-1-aryl-1H- tetrazoles but also to interesting side products, namely N-alkyl-N- arylcyanamides and (Z)-Se-alkyl-N-cyano-N,N′-diarylisoselenoureas. Nevertheless, when alkylisoselenocyanates were utilized as the substrates, the reactions led exclusively to the formation of 1-alkyl-5-alkylselanyl-1H- tetrazoles in good yields. This simple one-pot procedure brings new possibilities for the preparation of variously substituted selenium compounds. It also opens the way to further investigations of selenium isosteres of the widely utilized 5-thiotetrazole moiety in biomedical applications.

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.

Selenium-containing heterocycles from isoselenocyanates: 4-Methylselenazole derivatives from the reaction with malononitrile and propargyl chloride

Aryl isoselenocyanates 1 react with malononitrile (6a) and propargyl chloride (8) in DMF in the presence of Et3N to give the corresponding 2-(3-aryl-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene)malononitriles 12 as major products. The analogous

Synthesis of 5-selenoxo-1,2,4-triazole-1-carboxylates from isoselenocyanates and azodicarboxylates

A mixture of an azodicarboxylate and triphenylphosphine in dichloromethane reacted with aryl isoselenocyanates (1) at room temperature to give 4,5-dihydro-5-selenoxo-1H-1,2,4-triazole-1-carboxylates (4a-f) in a one-pot reaction in good to excellent yields

Synthesis of 3-acetyl-N-aryl-4-diethylaminoselenet-2(2H)-imines from 4-diethylamino-3-butyn-2-one and aryl isoselenocyanates

The reaction of aryl isoselenocyanates (1a-d) with 4-diethylamino-3-butyn-2-one (6) in refluxing tetrahydrofuran afforded N-arylselenet-2(2H)-imines (7) in moderate yields. The structure of the stable 4-bromophenyl derivative (7b) has been established by

Selenium-containing heterocycles from iso-selenocyanates: Synthesis of 2-arylamino-selenazolo[5,4-b]pyridines

The reaction of 3-amino-2-chloropyridine (4) with aryl isoselenocyanates (2a-d) in refluxing 2-propanol gave the hydrochlorides of 2-arylaminoselenazolo[5,4-b]pyridines (7a-d) in good yield. The free bases (8a-d) were obtained after treatment with aqueous NaOH and recrystallization. A reaction mechanism via the intermediate selenourea derivatives (5) is most likely. The structure of the 2-phenylamino derivative (8a) has been established by X-Ray crystallography.

Selenium-containing heterocycles from isoselenocyanates: Synthesis of 1H-5-selena-1,3,6-triazaaceanthrylene derivatives

The reaction of aryl isoselenocyanates 8 with methyl 3-amino-4-chloro-1-ethylpyrrolo[3,2-c]quinoline-2-carboxylate (6) in boiling pyridine leads to tetracyclic selenaheterocycles of type 9 in high yield (Scheme 3). A reaction mechanism via an intermediate