14223-48-4

Upstream product

• 64-18-6 formic acid 
• 106-47-8 4-chloro-aniline 
• 104-12-1 p-chlorphenylisocyanate 
• 1885-81-0 p-chlorophenyl isocyanide 
• 2617-79-0 N-(4-chlorophenyl)formamide 
• 506-80-9 carbon diselenide 

Downstream Products

• 16519-54-3 N-Phenyl-N'-(p-chlor-phenyl)-selenoharnstoff 
• 154592-71-9 N-(4-chlorophenyl)selenocarbamate of cholestanol 
• 634606-73-8 methyl 4-[(4-chlorophenyl)amino]-1-ethyl-1H-5-selena-1,3,6-triazaaceanthrylene-2-carboxylate 
• 905727-10-8 1-allyl-3-(4-chloro-phenyl)-selenourea 
• 1021489-11-1 2-[3-(4-chlorophenyl)-2,3-dihydro-4-methyl-1,3-selenazol-2-ylidene]propane-1,3-dinitrile 
• 24752-26-9 N-(4-chlorophenyl)-6-chloro-1H-benzo[d]imidazol-2-amine 
• 24752-30-5 N-(4-chlorophenyl)-1H-benzo[d]imidazol-2-amine 
• 1010687-39-4 N-(4-chlorophenyl)-6-nitro-1H-benzo[d]imidazol-2-amine 

Relevant academic research and scientific papers

Synthesis and leishmanicidal activity of novel urea, thiourea, and selenourea derivatives of diselenides

A novel series of thirty-one N-substituted urea, thiourea, and selenourea derivatives containing diphenyldiselenide entities were synthesized, fully characterized by spectroscopic and analytical methods, and screened for their in vitro leishmanicidal activities. The cytotoxic activity of these derivatives was tested against Leishmania infantum axenic amastigotes, and selectivity was assessed in human THP-1 cells. Thirteen of the synthesized compounds showed a significant antileishmanial activity, with 50% effective concentration (EC50) values lower than that for the reference drug miltefosine (EC50, 2.84 M). In addition, the derivatives 9, 11, 42, and 47, with EC50 between 1.1 and 1.95 M, also displayed excellent selectivity (selectivity index ranged from 12.4 to 22.7) and were tested against infected macrophages. Compound 11, a derivative with a cyclohexyl chain, exhibited the highest activity against intracellular amastigotes, with EC50 values similar to those observed for the standard drug edelfosine. Structure-activity relationship analyses revealed that N-aliphatic substitution in urea and selenourea is recommended for the leishmanicidal activity of these analogs. Preliminary studies of the mechanism of action for the hit compounds was carried out by measuring their ability to inhibit trypanothione reductase. Even though the obtained results suggest that this enzyme is not the target for most of these derivatives, their activity comparable to that of the standards and lack of toxicity in THP-1 cells highlight the potential of these compounds to be optimized for leishmaniasis treatment.

Thermal stability and decomposition of urea, thiourea and selenourea analogous diselenide derivatives

The fusion and thermal decomposition of thirty-three diselenide compounds with a urea, thiourea or selenourea group linked with different aliphatic or aromatic substituents have been studied by thermogravimetry, differential scanning calorimetry and mass spectrometry in order to perform comparative thermal stability studies among analogs. A relationship has been found between stability and a series of effects which occur in the compound structures. Analysis of the thermal data indicated that: (a) in general, compounds with a urea or selenourea group are more stable than those with a thiourea group; (b) no difference in stability exists when an aromatic or aliphatic group is linked to the thiourea group but when linked to the urea or selenourea groups, stability does differ; (c) selenourea compounds with aliphatic chain are the most unstable; and (d) the nature of the substituent located on the benzyl ring has no effects on thermal stability. Therefore, criteria for the selection of substituents can be established in order to improve the stability of these drugs. In addition, the mass spectral fragmentation in comparison with thermal analytical data helps in confirming the thermal behavior of the compounds.

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.

"On water": Efficient iron-catalyzed cycloaddition of aziridines with heterocumulenes

In suspension: The reaction of aziridines with heterocumulenes in the presence of Fe(NO3)3×9 H2O in aqueous suspension provides access to functionalized five-membered heterocycles in good to high yields. This protocol has a wide substrate scope, is simple, and uses a nontoxic and cheap catalyst. Copyright

One-pot synthesis of selenoureas and selenocarbamates via selenation of isocyanates with bis(dimethylaluminum) selenide

Isocyanates were efficiently selenated by the reaction with bis(dimethylaluminum) selenide to give the corresponding isoselenocyanates. One-pot synthesis of unsymmetrical selenoureas and selenocarbamates was achieved in high yields by the subsequent addit

Synthesis and pesticidal properties of thio and seleno analogs of some common urea herbicides

Thio and seleno analogs of fenuron, isoproturon, chlorotoluron, metoxuron, monuron, and diuron were synthesized from the corresponding aryl amines. Their reaction with thiophosgene leads to isothiocyanates. Aryl amines were also converted (via isocyanides) to isoselenocyanates. The reaction of both isothio- and isoselenocyanates with dimethylamine affords the corresponding thio and seleno analogs of the above-mentioned urea herbicides. Herbicidal activity of the synthesized compounds was slightly lower than the activity of the parent urea herbicides. The thio and seleno analogs as well as the parent ureas showed good fungicidal activity at a concentration of 200 ppm against selected fungi.

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

One-pot synthesis of 2-imino-1,3-selenazolidines by reaction of isoselenocyanates with propargylamine

One-pot synthesis of 2-imino-5-methylene-1,3-selenazolidines has been achieved by reactions of alkylisoselenocyanates with propargylamines in high yields. 1H NMR and NOESY experiments were used to explain the selenium coupling with hydrogen of

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