1441-85-6

Basic information

• Product Name: Benzoyl chloride, 2-(chloroseleno)-
• CAS NO: 1441-85-6
• Molecular Formula: C7H4Cl2OSe
• Molecular Weight: 253.974
• Mol File: 1441-85-6.mol
• Article Data: 56

Chemical Properties

• CAS DataBase Reference: Benzoyl chloride, 2-(chloroseleno)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoyl chloride, 2-(chloroseleno)-(1441-85-6)
• EPA Substance Registry System: Benzoyl chloride, 2-(chloroseleno)-(1441-85-6)

Safety Data

• Hazardous Substances Data: 1441-85-6(Hazardous Substances Data)

Usage

General Description

Benzoyl chloride, 2-(chloroseleno)- is a chemical compound that consists of a benzoyl group and a selenium atom bonded to a chlorine atom. It is commonly used as a reagent in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. Benzoyl chloride, 2-(chloroseleno)- is known for its strong reactivity, especially towards nucleophiles, and its ability to undergo substitution reactions. It is also used in the preparation of various organic selenium compounds, which are of interest in the field of medicinal chemistry due to their potential biological activities. Additionally, benzoyl chloride, 2-(chloroseleno)- is a valuable intermediate in the synthesis of other functionalized organic molecules.

Upstream product

• 6512-83-0 2,2'-diselanediyl-di-benzoic acid 
• 104101-90-8 2-selenocyanato-benzoic acid 
• 136918-14-4 phthalimide 
• 134-20-3 2-carbomethoxyaniline 
• 2099-63-0 anthranilic acid hydrochloride 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 17333-86-7 o-Carboxybenzenediazonium 
• 1441-84-5 2-selenocyanato-benzoyl chloride 
• 118-92-3 anthranilic acid 
• 10026-13-8 phosphorus pentachloride 
• 7719-09-7 thionyl chloride 

Downstream Products

• 60940-34-3 2-phenyl-1,2-benzoisoselenazol-3(2H)-one 
• 54996-53-1 2-methylbenzo[d][1,2]selenazol-3(2H)-one 
• 89780-24-5 2-(pyridin-3-yl)-1,2-benzisoselenazol-3(2H)-one 
• 124393-12-0 bis<(2-carboxyoctadecyl)phenyl> diselenide 
• 105893-02-5 diethyl 2,2'-diselenobisbenzoate 
• 124393-11-9 bis<(2-carboxydodecyl)phenyl> diselenide 
• 153871-75-1 4-(2,3-dihydro-3-oxo-1,2-benzisoselenazol-2-yl)benzoic acid 
• 328000-20-0 2-[3-(1-Oxyl-2,5,5-trimethylpyrrolidin-2-yl)phenyl]benzo[d]isoselenazol-3-one radical 
• 81744-01-6 2-(4'-hydroxyphenyl)-1,2-benzoisoselenazol-3(2H)-one 
• 847431-95-2 2-(2,4,6-triisopropylphenyl)-1,2-benzisoselenazol-3(2H)-one 
• 869303-21-9 2-[3-(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)phenyl]benzo[d]isoselenazol-3-one radical 
• 869303-22-0 2-{4-[1-(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-ylmethyl)piperazin-4-yl]phenylmethyl}benzo[d]isoselenazol-3-one radical 
• 81744-02-7 2-(3-hydroxyphenyl)-1.2-benzisoselenazol-3(2H)-one 
• 944719-58-8 2-(4-bromophenyl)benzo[d][1,2]selenazol-3(2H)-one 

Relevant articles and documents

Biomolecular Interaction Assays Identified Dual Inhibitors of Glutaminase and Glutamate Dehydrogenase That Disrupt Mitochondrial Function and Prevent Growth of Cancer Cells

Glutaminase (KGA/isoenzyme GAC) is an emerging and important drug target for cancer. Traditional methods for assaying glutaminase activity are coupled with several other enzymes. Such coupled assays do not permit the direct and stringent characterization of specific glutaminase inhibitors. Ebselen was identified as a potent 9 nM KGA inhibitor in the KGA/glutamate oxidase (GO)/horse radish peroxidase (HRP) coupled assay but showed very weak activity in inhibiting the growth of glutamine-dependent cancer cells. For rigorous characterization, we developed a direct kinetic binding assay for KGA using bio-layer interferometry (BLI) as the detection method; Ebselen was identified as a GDH inhibitor but not a KGA inhibitor. Furthermore, we designed and synthesized several benzo[d][1,2]selenazol-3(2H)-one dimers which were subjected to SAR analysis by several glutaminolysis specific biochemical and cell based assays. Novel glutamate dehydrogenase (GDH) or dual KGA/GDH inhibitors were discovered from the synthetic compounds; the dual inhibitors completely disrupt mitochondrial function and demonstrate potent anticancer activity with a minimum level of toxicity.

New glutathione peroxidase mimetics—Insights into antioxidant and cytotoxic activity

A series of N-alkyl benzisoselenazol-3(2H)-ones has been obtained and transformed to corresponding diselenides by the reduction with sodium borohydride. Additionally, efficient methodology for the oxidative Se–N bond formation by potassium iodate has been presented, new conversion of diselenide to benzisoselenazolone was observed. The GPx-like activity of all synthetized derivatives has been evaluated by NMR. N-Allyl diselenide was up to five times better antioxidant than ebselen. Anticancer capacity towards MCF7 and DU145 cancer cells has been also tested. The highest antiproliferative activity was obtained for N-cyclohexyl benzisoselenazolone.

New chiral ebselen analogues with antioxidant and cytotoxic potential

New chiral camphane-derived benzisoselenazol-3(2H)-ones and corresponding diselenides have been synthetized using a convenient one-pot procedure. Se-N bond was efficiently converted to an Se-Se bond, which could also be easily re-oxidized to the initial benzisoselenazolone moiety. The antioxidant activity of camphor derivatives was evaluated and compared to the reactivity of a series of N-amino acid benzisoselenazol-3(2H)-ones obtained by a modified procedure involving the improved synthesis and isolation of the diseleno bis(dibenzoic) acid. The most efficient peroxide scavengers, N-bornyl and N-leucine methyl ester benzisoselenazol-3(2H)-ones, were further evaluated as cytotoxic agents on four cancer cell lines (MCF-7, HEP G2, HL 6, and DU 145) and normal cell line PNT1A. The highest antiproliferative potential was evaluated for two compounds bearing a 3-methylbutyl carbon chain, N-leucine methyl ester and N-3-methylbutyl benzisoselenazol-3(2H)-ones.

Evaluation of Ebselen-azadioxatriangulenium as redox-sensitive fluorescent intracellular probe and as indicator within a planar redox optode

Redox homeostasis is essential for cellular survival and is therefore tightly regulated. Visualizing changes in the local redox state is essential for detecting oxidative stress, especially with the help of red, long emission lifetime probes. We synthesized a new reversible, redox-sensitive fluorescent probe, ebselen-azadioxatriangulenium (Ebselen-ADOTA), and characterized its potential use for intra- and extracellular redox sensing. The probe consists of a photostable triangulenium-based fluorophore (emission maximum at 564 nm) modulated by a redox-active ebselen motif. The reduced form only shows around 1/10 of the emission intensity of the oxidized form. The Ebselen-ADOTA probe exhibited reversible oxidation and reduction in solution under extracellular conditions. In addition, Ebselen-ADOTA can visualize an increase in oxidative stress within anaerobic bacteria when exposing them to air, the probe did not readily respond to changes in the redox environment inside mammalian cells, probably due to unfavorable localization, aggregation or binding to cysteine containing proteins. When incorporated inside a polymer matrix (hydrogel D4 mixed with poly(acrylic acid)), the probe showed a rapid and fully reversible response to redox changes, thus enabling the preparation of a redox-sensitive optode.

Novel ebselen-porphyrin conjugates: Synthesis and nucleic acid interaction study

Novel porphyrins bearing ebselen (2-phenyl-1,2-benzisoselenazol-3[2H]-one) moiety were synthesized and characterized. Their interactions with herring sperm DNA were studied by means of UV-visible, fluorescence, circular dichroism spectroscopy, and gel electrophoresis.

Synthesis of new alkylated and methoxylated analogues of ebselen with antiviral and antimicrobial properties

A series of new mono and disubstituted alkylated and methoxylated benzisoselanzol-3(2H)-ones and bis(2carbamoylaryl)diselenides were prepared in yields ranging from 55% to 95% starting from anthranilic acid and were evaluated for antiviral and antimicrobial activity. The compounds exhibited antiviral activity against Human herpes virus 1 and Encephalomyocarditis virus as well as antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Candida albicans. R1 O O R1 COOH N N R2 H Se R2 NH2 Se 2 R1, R2 = Me, OMe, Cl, t-Bu, H.

Crystal form of 1, 4-[bis(1, 2-benzisoselenazole-3(2H)-ketone)] butane and preparation method and application thereof

The crystal form I of 1, 4-[bis(1, 2-benzisoselenazole-3(2H)-ketone)] butane is radiated by Cu-Kalpha, and X-ray powder diffraction expressed by a 2theta angle has characteristic peaks at 6.17+/-0.20degree, 12.28+/-0.20 degree, 18.44+/-0.20 degree, 25.92+/-0.20 degree and 30.95+/-0.20 degree. The crystal form has good stability, is not suitable for crystal transformation, is beneficial to preparation, use, transportation and storage of pharmaceutical compositions and preparations, and fully guarantees the medication safety and the drug quality. In addition, the crystal form has high solubility, reasonable bioavailability, low toxicity and excellent tumor inhibition activity.