21856-92-8

Upstream product

• 120-72-9 indole 
• 3425-46-5 potassium selenocyanate 
• 7677-24-9 trimethylsilyl cyanide 
• 24442-69-1 malononitrile 
• 2179-96-6 triselenium dicyanide 
• 109-77-3 malononitrile 

Downstream Products

• 21914-06-7 3,3'-Bis-indolyl-diselenid 

Relevant academic research and scientific papers

3-Selenocyanate-indoles as new agents for the treatment of superficial and mucocutaneous infections

The development of resistance to the current antifungal agents is an alarming problem. Therefore, the search for new molecules capable of combating fungi infections is imperative. This study presents the in vitro activities of a library of seven 3-selenocyanate-indoles against Candida spp. and dermatophytes of the genera Trichophyton and Microsporum. The antifungal susceptibility of compounds 4a and 4b presented geometric mean values of 4.1 and 6.0 μg mL?1 against Candida spp. and 1.2 and 2.2 μg mL?1 against dermatophytes following the CLSI guidelines. The 3-selenocyanate-indole 4a showed a fungicidal effect against the whole fungal panel. The toxicological results revealed that the selenocyanates 4a and 4b did not show mutagenicity or cause changes in the human leukocyte cells and were classified as non-irritant by the ex vivo HET-CAM test. The mechanism of action of the 3-selenocyanate-indoles has not been clearly elucidated. However, a genotoxic potential in higher concentrations, observed by the comet assay, leads us to believe that these molecules have their mechanism of action related to the nucleus of the fungal cells.

Polarization-induced charge separation in conjugated microporous polymers for efficient visible light-driven C-3 selenocyanation of indoles

Conjugated microporous polymers (CMPs) are cost-effective photocatalysts in organic transformations, while they are usually limited by the insufficient separation of photogenerated charges. Here we report a polarization strategy through molecular geometry optimization to promote the charge separation of CMPs. Three CMP photocatalysts with an alternative donor-acceptor skeleton and tunable symmetry were synthesized by the oxidative coupling of bis-carbazoles with electron-deficient bridges (benzene/pyridine/pyrimidine). Simply regulating the polarization of the starting monomers leads to tailorable porosity, photoelectric properties, and photocatalytic activity of the CMPs. They exhibited high efficiency in C-3 selenocyanation of indoles under visible-light and at room temperature, and pyridine-based CMPs with the largest dipole moment gave a yield of up to 94%, superior to their state-of-the-art photocatalyst counterparts. Photo-physical experiments combined with theoretical calculations further supported that the incorporation of the polarized linker introduced an internal electric field, benefitting efficient charge separation. This offered new insight into developing high-performance photocatalysts.

Long Vibrational Lifetime R-Selenocyanate Probes for Ultrafast Infrared Spectroscopy: Properties and Synthesis

Ultrafast infrared vibrational spectroscopy is widely used for the investigation of dynamics in systems from water to model membranes. Because the experimental observation window is limited to a few times the probe's vibrational lifetime, a frequent obstacle for the measurement of a broad time range is short molecular vibrational lifetimes (typically a few to tens of picoseconds). Five new long-lifetime aromatic selenocyanate vibrational probes have been synthesized and their vibrational properties characterized. These probes are compared to commercial phenyl selenocyanate. The vibrational lifetimes range between 400 and 500 ps in complex solvents, which are some of the longest room-temperature vibrational lifetimes reported to date. In contrast to vibrations that are long-lived in simple solvents such as CCl4, but become much shorter in complex solvents, the probes discussed here have ～400 ps lifetimes in complex solvents and even longer in simple solvents. One of them has a remarkable lifetime of 1235 ps in CCl4. These probes have a range of molecular sizes and geometries that can make them useful for placement into different complex materials due to steric reasons, and some of them have functionalities that enable their synthetic incorporation into larger molecules, such as industrial polymers. We investigated the effect of a range of electron-donating and electron-withdrawing para-substituents on the vibrational properties of the CN stretch. The probes have a solvent-independent linear relationship to the Hammett substituent parameter when evaluated with respect to the CN vibrational frequency and the ipso 13C NMR chemical shift.

N -Selenocyanato-Dibenzenesulfonimide: A New Electrophilic Selenocyanation Reagent

A new electrophilic selenocyanation reagent N -seleno-cyanato-dibenzenesulfonimide was readily prepared in two steps from commercially available dibenzenesulfonimide for the first time. A variety of electrophilic selenocyanato reactions of nucleophiles have been achieved using it as selenocyanato source under mild and simple conditions. Numerous SeCN-containing compounds were obtained in moderate to excellent yields. Meanwhile, a Lewis acid mediated tandem selenocyanation/cyclization reaction of alkenes with phenols, which provided simple methods for the formation of various SeCN-containing chromanes and dihydrobenzofurans in moderate to good yields, has also been developed.

Facile, regioselective oxidative selenocyanation of: N -aryl enaminones under transition-metal-free conditions

A direct and straightforward approach for the regioselective selenocyanation of N-aryl enaminones through sp2 C-H functionalization has been realized at room temperature. In this study, KSeCN as the selenocyanate reagent and K2S2O8 as the oxidizing agent are employed under transition-metal-free conditions. The present methodology was also applied for the synthesis of selenocyanated chromones, indoles and anilines in good to excellent yields.

Oxidative umpolung selenocyanation of ketones and arenes: An efficient protocol to the synthesis of selenocyanates

A practical method for the umpolung selenocyanation of aryl ketones, alkyl ketones, β-ketoesters and electron-rich arenes has been developed, affording various selenocyanates in moderate to excellent yields. This transformation proceeds by an oxidative um

Method for synthesizing 3-selenocyanoindole compound

The invention belongs to the field of organic synthesis, and discloses a method for synthesizing a 3-selenocyanoindole compound. According to the method, elemental selenium and TMS-CN are used as novel selenocyano sources to realize selective selenocyanat

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NH4SCN and KSeCN are employed respectively as the sole reagent.

Synthesis and evaluation of benzimidazole carbamates bearing indole moieties for antiproliferative and antitubulin activities

A series of novel benzimidazole carbamates bearing indole moieties with sulphur or selenium atoms connecting the aromatic rings were synthesised and evaluated for their antiproliferative activities against three human cancer cell lines (SGC-7901, A-549 and HT-1080) using an MTT assay. Compounds 10a, 10b, 7a, 7b and 7f showed significant activities against these cell lines. The most potent compound in this series, 10a, was selected to investigate its antitumour mechanism. In addition, molecular docking studies suggested that compound 10a interacts very closely with the nocodazole docking pose through hydrogen bonds at the colchicine binding site of tubulin.

Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates

Triselenium dicyanide is formed by the interaction of malononitrile and selenium dioxide in dimethylsulfoxide or dimethylformamide. Addition of aromatic amines, indoles and some active methylene compounds to this reaction mixture gives the corresponding s