83293-39-4

Upstream product

• 4671-93-6 benzyl selenocyanate 
• 100-14-1 4-nitrobenzyl chloride 
• 3425-46-5 potassium selenocyanate 
• 100-44-7 benzyl chloride 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 114082-88-1 tert-Butyl-dimethyl-[(1S,3R,4R)-3-(4-nitro-phenyl)-2-selena-bicyclo[2.2.2]oct-5-en-6-yloxy]-silane 
• 114082-89-2 tert-Butyl-dimethyl-[(1R,3S,4S)-3-(4-nitro-phenyl)-2-selena-bicyclo[2.2.2]oct-5-en-5-yloxy]-silane 
• 30876-61-0 bis(4-nitrobenzyl)diselenide 
• 100-14-1 4-nitrobenzyl chloride 

Relevant academic research and scientific papers

(1-Selenocyanatoethyl)benzene: A Selenocyanation Reagent for Site-Selective Selenocyanation of Inert Alkyl C(sp3)-H Bonds

A new, simple, yet easily accessible, (1-selenocyanatoethyl)benzene has been designed and applied as a SeCN group transfer reagent for selenocyanation of aliphatic C(sp3)-H bonds for the first time. This protocol is featured with mild reaction conditions and wide substrate scope. Control experiments reveal that a radical-group transfer mechanism might be involved.

Pronounced activity of aromatic selenocyanates against multidrug resistant ESKAPE bacteria

Selenocyanates represent an interesting class of organic selenium compounds. Due to their similarity with better known natural (iso-)thiocyanates, they promise high biological activity and may also be metabolized to other Reactive Selenium Species (RSeS),

Potent anti-proliferative activities of organochalcogenocyanates towards breast cancer

The pharmacological importance, particularly the anti-cancer and chemopreventive potentials, of organochalcogen compounds has attracted wide research attention recently. Herein we describe the synthesis of a series of organochalcogenocyanates that have one or more selenocyanate or thiocyanate units in a single molecule. The anti-proliferative activity of these organochalcogenocyanates in different breast cancer cells shows that selenocyanates exhibit much higher anti-proliferative activities than thiocyanates in general. Our study reveals that the activity of benzyl selenocyanate (1, BSC) could be significantly enhanced by 4-nitro substitution (12), which was more selective towards triple-negative breast cancer cells (MDA-MB-231) over other ER+ breast cancer cells (MCF-7 and T-47D). Furthermore, to the best of our knowledge, this is the first report on the synthesis of compounds having more than two selenocyanate units with promising anti-proliferative activities. Our studies further indicate that the apoptotic activities of selenocyanates are associated with modulation of cellular morphology and cell cycle arrest at S-phase. Selenocyanates also inhibited cellular migration and exhibited weak antioxidant activities. An effective binding interaction of compound 12 with serum albumin indicates its feasible transport in the bloodstream for its enhanced anti-cancer properties. Mechanistic studies by western blot analysis demonstrate that benzylic selenocyanates exhibit anti-proliferative activities by modulating key cellular proteins such as Survivin, Bcl-2 and COX-2; this was further supported by molecular docking studies. The results of this study would be helpful in designing suitable chemotherapeutic and chemopreventive drugs in the future.

Tetrazole regioisomers in the development of nitro group-containing antitubercular agents

Tetrazole derivatives containing nitro substituents have been identified as promising antitubercular agents. In this study, the antitubercular potency, selectivity and toxicity of tetrazole 1,5- and 2,5-regioisomers were examined. We prepared a series of 1- and 2-alkyl-5-benzylsulfanyl-2H-tetrazoles and their selenium analogs with various nitro group substitutions. These 1,5- and 2,5-regioisomers were isolated and unambiguously identified using 1H and/or 13C NMR. Among the prepared compounds, 1- and 2-alkyl-5-[(3,5-dinitrobenzyl)sulfanyl]-2H-tetrazole derivatives and their selenium bioisosteres showed the highest antimycobacterial activity, with minimal inhibitory concentration (MIC) values of approximately 1 μM (0.37-0.46 μg mL-1) against Mycobacterium tuberculosis CNCTC My 331/88. The 2-alkyl regioisomers exhibited consistently higher antimycobacterial activity and lower in vitro toxicity against a mammalian cell line compared to the 1-alkyl isomers. The antimycobacterial activity of the 2-alkyl regioisomers was less influenced by the type of alkyl substituent in contrast to 1-alkyl isomers. Furthermore, the 3,5-dinitrobenzyl moiety per se is not the carrier of mutagenicity. These findings encourage further optimization of the 2-alkyl chain to improve the pharmacokinetic properties and toxicity of 2-alkyl-5-[(3,5-dinitrobenzyl)sulfanyl]-2H-tetrazole lead compounds. This journal is

Selenocyanates and diselenides: A new class of potent antileishmanial agents

Thirty five selenocyanate and diselenide compounds were subjected to in vitro screening against Leishmania infantum promastigotes and the most active ones were also tested in an axenic amastigote model. In order to establish the selectivity indexes (SI) t

Highly chemoselective synthesis of functionalized diselenides from alkyl halides using benzyltriethylammonium tetrathiomolybdate

A variety of functionalized selenocyanates generated in situ from the corresponding alkyl halides undergo a facile reductive coupling on treatment with benzyltriethylammonium tetrathiomolybdate 1 under very mild conditions to give the corresponding disele

Synthesis and Cycloaddition Reactivity of Selenoaldehydes

A variety of substituted selenoaldehydes has been prepared via fluoride desilylation of α-silyl selenocyanates or base-induced elimination of HCN from simple selenocyanates containing electron-accepting or conjugating substituents.Cycloaddition reactions

Reactions of Benzylic Compounds. Nucleophilicity, Leaving Group Ability and Carbon Basicity of some Ionic Nucleophiles in Acetonitrile. Comments on the Utility of the Finkelstein Reaction in Synthesis

The reactions of some 4-substituted benzylic compounds, 4-Z-PhCH2X, with various ionic nucleophiles, Y(-), (Z = NO2, H and Me; X and Y = Cl,Br,SCN and SeCN) have been studied under homogeneous conditions in acetonitrile at 25.0 deg C.All the reactions have been found to proceed through nucleophilic attack at the methylene carbon atom.Isothiocyanates, 4-Z-PhCH2NCS, and isoselenocyanates, 4-Z-PhCH2NCSe, are not formed.The reactions obey second-order kinetics, first order in each of the reactants.The halide ions and the selenocyanate ion show similar nucleophilic strength and are five to ten times as reactive as the thiocyanate ion.The average leaving group ability is I(-) > Br(-) >> Cl(-) > NCSe(-) > NCS(-).From the equilibrium constants the average carbon basicity order is NCSe(-) ca.NCS(-) ca.Cl(-) >> Br(-) > I(-).The relative basicity of NCSe(-), NCS(-) and Cl(-) is slightly dependent upon Z; in 4-Me-PhCH2X the order is NCS(-) >/= NCSe(-) > Cl while in 4-NO2-PhCH2X the order is NCSe(-) > NCS(-) ca.Cl(-).The tellurocyanate ion, NCTe(-), is ten times as reactive as NCSe(-) toward 4-NO2-PhCH2Cl and no equilibrium is established (K > 1E4).The reaction product is an addition compound from the first formed organic tellurocyanate and the displaced chloride ion, the (-) - anion, a Te(II)-tellurate.The results from an X-ray structure determination of is presented in brief.In the adduct Cl is trans to the cyano group and the Te-Cl bond, 2.923(2) Angstroem, is more than 1 Angstroem shorter than the sum of the van der Waal's radii.