262-05-5

Usage

General Description

10H-Phenoselenazine is a chemical compound with the molecular formula C13H9NSe. It is a heterocyclic compound containing a selenazole ring, and it is also known as benzoselenadiazole. 10H-Phenoselenazine is a potential candidate for pharmaceutical research due to its diverse biological activities, including anti-cancer, anti-bacterial, and anti-inflammatory properties. The compound has shown promising results in inhibiting the growth of cancer cells and reducing inflammation in experimental studies. Its unique structure and potential pharmacological properties make 10H-Phenoselenazine an interesting target for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C12H9NSe/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H

Upstream product

• 122-39-4 diphenylamine 
• 65848-40-0 2-(phenylseleno)nitrobenzene 
• 552-16-9 ortho-nitrobenzoic acid 
• 1666-13-3 diphenyl diselenide 
• 41962-55-4 copper(I) benzeneselenide 
• 609-73-4 o-nitroiodobenzene 

Downstream Products

• 86-74-8 9H-carbazole 
• 2934-35-2 10-<3-Dimethylamino-propyl>-2-propionyl-phenselenazin 

Relevant academic research and scientific papers

Revealing the internal heavy chalcogen atom effect on the photophysics of the dibenzo[a,j]phenazine-cored donor-acceptor-donor triad

A new twisted donor-acceptor-donor (D-A-D) multi-photofunctional organic molecule comprising phenoselenazine as the electron donor (Ds) and dibenzo[a,j]phenazine (DBPHZ) as the electron acceptor (A) has been developed. The developed selenium-incorporated D-A-D compound features multi-color polymorphism, distinct mechanochromic luminescence, chemically-stimulated luminochromism, thermally-activated delayed fluorescence, and room-temperature phosphorescence. The internal heavy atom effect on the photophysical properties of the D-A-D system has been investigated through a comparison with the physicochemical properties of a previously developed sulfur analogue and a tellurium analogue.

Dehydrogenative C-H phenochalcogenazination

Heavy-atom-modified chalcogen-fused triarylamine organic materials are becoming increasingly important in the photochemical sciences. In this context, the general and direct dehydrogenative C-H phenochalcogenazination of phenols with the heavier chalcogen

Tellurium(II)/Tellurium(III)-Catalyzed Cross-Dehydrogenative C?N Bond Formation

The TeII/TeIII-catalyzed dehydrogenative C?H phenothiazination of challenging phenols featuring electron-withdrawing substituents under mild aerobic conditions and with high yields is described. These unexpected TeII/Tesu

Antitubercular polyhalogenated phenothiazines and phenoselenazine with reduced binding to CNS receptors

Targeting energy metabolism in Mycobacterium tuberculosis (Mtb) is a new paradigm in the search for innovative anti-TB drugs. NADH:menaquinone oxidoreductase is a non-proton translocating type II NADH dehydrogenase (NDH-2) that is an essential enzyme in the respiratory chain of Mtb and is not found in mammalian mitochondria. Phenothiazines (PTZs) represent one of the most known class of NDH-2 inhibitors, but their use as anti-TB drugs is currently limited by the wide range of potentially serious off-target effects. In this work, we designed and synthesized a series of new PTZs by decorating the scaffold in an unconventional way, introducing various halogen atoms. By replacing the sulfur atom with selenium, a dibromophenoselenazine 20 was also synthesized. Among the synthesized poly-halogenated PTZs (HPTZs), dibromo and tetrachloro derivatives 9 and 11, along with the phenoselenazine 20, emerged with a better anti-TB profile than the therapeutic thioridazine (TZ). They targeted non-replicating Mtb, were bactericidal, and synergized with rifampin and bedaquiline. Moreover, their anti-TB activity was found to be related to the NDH-2 inhibition. Most important, they showed a markedly reduced affinity to dopaminergic and serotonergic receptors respect to the TZ. From this work emerged, for the first time, as the poly-halogenation of the PTZ core, while permitting to maintain good anti-TB profile could conceivably lead to fewer CNS side-effects risk, making more tangible the use of PTZs for this alternative therapeutic application.

ORGANIC LIGHTEMITTING COMPOUND HAVING PHOSPHORESCENT CHARACTERISTIC AT ROOM TEMPERATURE, AND PHOSPHORESCENT ORGANIC LIGHT EMITTING DEVICE INCLUDING THE ORGANIC LIGHTEMITTING COMPOUND

Disclosed is an organic light-emitting compound having a phosphorescent characteristic at room temperature and a phosphorescent organic light-emitting device containing the same. The organic light-emitting compound includes a compound represented by a fol

Copper-catalyzed: Ipso -selenation of aromatic carboxylic acids

The copper-catalyzed decarboxylative selenation of aromatic carboxylic acids with diselenide is reported. This transformation tolerated a diverse set of functional groups on the substrates, including pentafluorobenzoic acid and heteroaromatic acids, delivering diaryl and methyl aryl selenides in good to excellent yields. Mechanistic studies indicated that the copper catalyst is essential in the activation of the Se-Se bond and the decarboxylation of aromatic acids. The utility of the products has been demonstrated in the facile synthesis of 10H-phenoselenazine and 11-methyldibenzo-(b,f)-1,4-selenazepine.

10-hydrophenoselenazine compound and preparation method

The invention relates to a 10-hydrophenoselenazine compound and a preparation method. The 10-hydrophenoselenazine compound is obtained through subjecting (2-nitrobenzene)phenyl selenide, which serves as a reactant, to an intramolecular cyclization reaction under the reduction action of triphenylphosphine in an organic solvent under nitrogen conditions. According to the method, the reaction conditions are simple, the experiment aftertreatment is simple and convenient, the product is high in yield and purity, and new synthesis routes and methods are developed for the 10-hydrophenoselenazine compound, so that the compound has good potential applications and research values.

Tricyclic phenothiazine and phenoselenazine derivatives as potential multi-targeting agents to treat Alzheimer's disease

A group of tricyclic phenothiazines (6a, 6b and 7a-l) and phenoselenazines (12a, 12b and 13a-l) was designed, synthesized and evaluated as multi-targeting ligands aimed at the cholinergic, amyloid and oxidative stress pathways of Alzheimer's disease. The phenothiazine derivative 7j (2-chloro-10H-phenothiazin-10-yl-(4-methoxyphenyl)methanone) was identified as the best dual, non-selective cholinesterase inhibitor (AChE IC50 = 5.9 ± 0.6 μM; BuChE IC50 = 5.3 ± 0.5 μM), whereas in the corresponding phenoselenazine series, 13j (2-chloro-10H-phenoselenazin-10-yl-(4-methoxyphenyl)methanone) exhibited good non-selective cholinesterase inhibition (AChE IC50 = 5.8 ± 0.4 μM; BuChE IC50 = 4.9 ± 0.5 μM). Interestingly, N-10 unsubstituted phenothiazine 6a (AChE IC50 = 7.3 ± 0.6 μM; BuChE IC50 = 5.8 ± 0.5 μM; Aβ1-42 aggregation inhibition = 62%; DPPH scavenging = 92%), and the corresponding phenoselenazine bioisostere 12a (AChE IC50 = 5.6 ± 0.4 μM; BuChE IC50 = 3.0 ± 0.5 μM; Aβ1-42 aggregation inhibition = 45.6%; DPPH scavenging = 84.4%) were able to exhibit multi-targeting ability by demonstrating cholinesterase inhibition, beta-amyloid aggregation and antioxidant properties. These results show that fused tricyclic ring systems based on either phenothiazine or phenoselenazine templates can be useful to develop hybrid small molecules to target multiple pathological routes associated with Alzheimer's disease.

PHOTOSENSITISERS AND THEIR USES

A phenoselenazinium compound of Formula (1): wherein: R1 - R6 each independently is selected from H, optionally substituted alkyl, optionally substituted alkoxy, F, CI, Br and I; A and B each independently is selected from Formula (2): in which: Q is selected from H and optionally substituted alkyl; Z is selected from C(Ra)2, O, S, SO2, NRa in which each Ra independently is selected from H and optionally substituted alkyl; R7 and R8 each independently is selected from H and optionally substituted alkyl; Y is a counteranion; and p is 1, 2or 3, except for 3,7-bis(dimethylamino)-phenoselenazin-5-ium chloride and the corresponding bromide and iodide, and the compound in which R1 to R4, and R6 are all H, R5 is methyl, A is NMe2 and B is NH2 and their use in photodynamic therapy (PDT) particularly their use as anti-infectives, as anti-cancer agents, and as sterilising agents both for direct use and in combination with a polymer.