23243-47-2

Upstream product

• 115423-27-3 3-hydroxypropyl selenocyanate 
• 627-18-9 1-bromo-3-propanol 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 115423-32-0 benzyl 3-hydroxypropyl selenide 

Relevant academic research and scientific papers

A facile access to chalcogen and dichalcogen bearing dialkylamines and diols

A highly practical procedure for the preparation of novel classes of chalcogen bearing diamines [{H2N(CH2)n} 2E] and diols [{HO(CH2)n}2E] (n = 2 or 3 and E = Se or Te) by the reaction of disodiumchalcogenide and haloalkylamines or haloalcohols is presented.

Synthesis of a GNRs@mSiO2-ICG-DOX@Se-Se-FA Nanocomposite for Controlled Chemo-/Photothermal/Photodynamic Therapy

A novel GNRs@mSiO2 core–shell nanocomposite has been synthesized to integrate sensitive chemotherapy with photodynamic therapy (PDT) and photothermal therapy (PTT) for enhanced antitumor treatment by using gold nanorods (GNRs) as the core and mesoporous silica (mSiO2) as the shell. After modifying with -NH2, Indocyanine Green (ICG, negative charge) and doxorubicin hydrochloride (DOX, positive charge) molecules could be stored in the mesopores by the layer-by-layer assembly method through electrostatic interactions. To inhibit leakage from the mesopores, a sensitive Se–Se linker was synthesized and adopted as a nanovalve coated on the outside of the nanoparticles (GNRs@mSiO2-ICG-DOX@Se-Se). Under NIR (808 nm) irradiation, heat elevation (derived from GNR/ICG) and generation of reactive oxygen species (ROS, derived from ICG) can also be detected in vitro. Owing to the redox sensitivity of Se–Se, GNRs@mSiO2-ICG-DOX@Se-Se showed reduction (GSH)- as well as oxidation (ROS)-triggered DOX release. To further ensure specific targeting, folic acid (FA) was grafted to the outside of the nanoparticles, because of the high expression of FA receptors on tumor cells. Detailed cell experiments performed with the nanoparticles and HepG2 as typical cancer cells showed enhanced cytotoxicity towards the cancer cells owing to the synergistic effect of chemotherapy, PTT, and PDT. On account of the different GSH concentrations in cancer and normal cells and the switch-on/off application of NIR irradiation, the GNRs@mSiO2-ICG-DOX@Se-Se-FA nanoparticles show potential for applications in cancer therapy.

Healable and Rearrangeable Networks of Liquid Crystal Elastomers Enabled by Diselenide Bonds

Based on liquid crystal elastomer (LCE) materials, hierarchically structured soft actuators can meet some requirements for “human-friendly” working mode and execute complex tasks with intelligent adaptation to environmental changes. However, few researchers have paid much attention to the preparation methods of multicomponent/hierarchical LCE actuators. In this communication, we demonstrate the successful integration of an exchangeable diselenide chain extender for the preparation of dynamic LCEs, which could be reprogrammed on heating or under visible light illumination. Moreover, the rearrangeable polydiselenide networks could be applied to develop the self-welding technology toward fabricating hierarchically structured LCE actuators with sophisticated deformability without using any auxiliary reagent (adhesive, tape, catalysts or initiator) during the assembling process.

Diselenides and Allyl Selenides as Glutathione Peroxidase Mimetics. Remarkable Activity of Cyclic Seleninates Produced in Situ by the Oxidation of Allyl ω-Hydroxyalkyl Selenides

A series of aliphatic diselenides and selenides containing coordinating substituents was tested for glutathione peroxidase (GPx)-like catalytic activity in a model system in which the reduction of tert-butyl hydroperoxide with benzyl thiol to afford dibenzyl disulfide and tert-butyl alcohol was performed under standard conditions and monitored by HPLC. Although the diselenides showed generally poor catalytic activity, allyl selenides proved more effective. In particular, allyl 3-hydroxypropyl selenide (25) rapidly generated 1,2-oxaselenolane Se-oxide (31) in situ by a series of oxidation and [2,3]sigmatropic rearrangement steps. The remarkably active cyclic seleninate 31 proved to be the true catalyst, reacting with the thiol via a postulated mechanism in which the thioseleninate 32 is first produced, followed by further thiolysis to selenenic acid 33 and oxidation-dehydration to regenerate 31. In contrast to catalysis with GPx, formation of the corresponding selenenyl sulfide 34 comprises a competing deactivation pathway in the catalytic cycle of 31, as a separate experiment revealed that authentic 34 was a much less effective catalyst than 31. 1,2-Oxaselenane Se-oxide (37), the six-membered homologue of 31, was formed similarly from allyl 4-hydroxybutyl selenide (26), but proved a less effective catalyst than 31. Compounds 31 and 37 are the first examples of unsubstituted monocyclic seleninate esters.

Remarkable activity of a novel cyclic seleninate ester as a glutathione peroxidase mimetic and its facile in situ generation from allyl 3-hydroxypropyl selenide

1,2-Oxaselenolane Se-oxide is a novel cyclic seleninate ester that functions as a remarkably efficient glutathione peroxidase mimetic by catalyzing the reduction of tert-butyl hydroperoxide to tert-butyl alcohol in the presence of benzyl thiol. The seleni

One-pot two-step approach to selenides. Phase-transfer catalyzed synthesis of ω-hydroxyalkyl selenides

ω-hydroxyalkyl selenides were synthesized in good yields under phase- transfer conditions which involved hadrazine reduction on selenium powder and then alkylation with ω-haloalkyl alcohols in the presence of TBAB, reduction the resulting diselenides with KBH4 followed by treatment with alkyl halides.

Synthesis of cyclic halooxatelluranes via dehalogenation of α-halo carbonyl compounds with tellurides containing hydroxy group on side chain

The synthesis of cyclic halooxatelluranes (3a, 4a-d, 5a) has been achieved via dehalogenation of α-halo carbonyl compounds (2A-F) with tellurides(1a-d) containing hydroxy group on the side chain. Halophilicity of the tellurides was compared with that of selenides and a plausible reaction mechanism is discussed.

Structure-activity studies on organoselenium alkylating agents

A variety of organoselenium alkylating agents were synthesized, using 2-hydroxyethyl and 3-hydroxypropyl selenocyanate intermediates, and studied to determine their chemical reactivities with 4-(4-nitrobenzyl) pyridine (NBP) and cytotoxicities against CCRF-CEM, L1210/0, and L1210/L-PAM cells. The comparison between the 2-chloroethyl sulfides and selenides 1-4 revealed the markedly enhanced nucleophilicity of selenium (Se) over sulfur (S) by two or more orders of magnitude. This finding indicates that a major consideration in the design of antitumor alkylating organoselenides is the reactivity of selenium. A Taft plot of the experimental first-order rate constant, k'(nbp), and σ* in a series of 2-chloroethylseleno compounds gave a slope of -1.73 (ρ*), with the exception of 2-chloroethyl 2-nitrophenyl selenide (10). The anomalous behavior of 10 is explained in terms of the ortho-nitro stabilization effect directly interacting with the selenium atom of ethyleneselenonium ion to form a 5-membered cyclic intermediate. In the same series, a 5000-fold difference in alkylating reactivity offered only a sixfold variation in cytotoxicity against CCRF-CEM cells. Increasing the alkylating chain length from ethylene to propylene units markedly reduced alkylating reactivities. In the CH3Se(CH2)(n)Cl series, 16 (n = 3) was 1.5 x 105 times slower than 2 (n = 2) in NBP alkylation, revealing that 3-chloro-n-propyl selenides are not chemically reactive enough to be biological alkylating agents despite the presence of the highly nucleophilic selenium atom. Replacement of chloride with mesylate in 3-substituted propyl selenides, such as 17 and 20, restored desirable reactivities and cytotoxicities.