Name | Ebselen |
Synonyms | Ebselen DR-3305 RP-60931 Harmokisane 2-phenyl-1,2-benzisoselenazol- 2-Phenyl-1,2-benzoselenazol-3-one 2-Phenyl-1-selena-2-azaindan-3-one 2-phenyl-1,2-benzoselenazol-3(2H)-one 2-Phenyl-1,2-benzisoselenazol-3(2H)-one Ebselen2-Phenyl-benzo[d]isoselenazol-3-one 2-PHENYL-1,2-BENZOSELENAZOL-3-ONE(EBSELEN) |
CAS | 60940-34-3 |
EINECS | 612-054-8 |
InChI | InChI=1/C13H9NOSe/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10/h1-9H |
InChIKey | DYEFUKCXAQOFHX-UHFFFAOYSA-N |
Molecular Formula | C13H9NOSe |
Molar Mass | 274.18 |
Melting Point | 176-182 °C |
Boling Point | 402.8±28.0 °C(Predicted) |
Flash Point | 197.4°C |
Solubility | Solubility in water: insoluble Solubility in other solvents: soluble in methanol, ethanol, THF, ethyl acetate, DMSO |
Vapor Presure | 1.07E-06mmHg at 25°C |
Appearance | Crystalline Powder |
Color | Yellow to beige |
Merck | 14,3486 |
pKa | -0.40±0.20(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
MDL | MFCD00210937 |
Risk Codes | R23/25 - Toxic by inhalation and if swallowed. R33 - Danger of cumulative effects R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S20/21 - S28 - After contact with skin, wash immediately with plenty of soap-suds. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A - S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
UN IDs | UN 3283 6.1/PG 3 |
WGK Germany | 3 |
RTECS | DE4140750 |
HS Code | 29310099 |
Hazard Class | 6.1 |
Packing Group | III |
1mg | 5mg | 10mg | |
---|---|---|---|
1 mM | 3.647 ml | 18.236 ml | 36.472 ml |
5 mM | 0.729 ml | 3.647 ml | 7.294 ml |
10 mM | 0.365 ml | 1.824 ml | 3.647 ml |
5 mM | 0.073 ml | 0.365 ml | 0.729 ml |
function | ebse is a small molecule antioxidant, easy to participate in various redox reactions, can remove excessive peroxides in the body, blocking the chain reaction of free radicals, so it can treat a variety of diseases and maintain the normal physiological function of the body. For a long time, it is generally believed that ebse plays a role in vivo mainly by mimicking the reaction mechanism of glutathione peroxidase. However, recent studies have shown that ebse tends to act more in vivo through thioredoxin reductase and The thioredoxin response system. |
preparation | There are three main methods for the synthesis of ebse: A. N-phenylbenzamide was used as the starting material, and its Ortho-position was lithiated by n-BuLi to form a C- Li bond, and then the Se atom was inserted into a C- Li bond to form a double anion compound, finally, ebse was obtained by ring-closure by oxidation with an appropriate oxidant. When Br2 or I2 was used as oxidant, the yield of ring closure was less than 20%, when FeCl3 was used, the yield of ring closure was increased to 42%, and when CuBr2 was used, the yield was further increased to 63%. B. With 2,2 '-diselenated dibenzoic acid as starting material, substituted 2-methylselenylbenzamide was obtained by multi-step reaction, and ebse was obtained by PCl5 ring closure and hydrolysis. C. With 2,2 '-diselenated bisbenzoic acid as a starting material, Lesser and Kamigata et al. cleave the diselenide bond through SOCl2 to form intermediate 3, and then react with aniline to ring-close to obtain ebse. |
biological activity | Ebselen (DR SPI-1005, PZ-51, CCG-39161, HIV-1) is a small molecule capsid inhibitor with replication, the IC50 in the assay TR-FRET was 46.1 nM. |
Target | Value |
HIV-1 (Cell-free assay) | 46.1 nM |
Cell Line: | COVID-19 virus infected Vero cells |
Concentration: | 0.4, 1.2, 3.7, 11.1, 33.3, 100 μM |
Incubation Time: | 20-24 hours |
Result: | Showed strong antiviral effects at a concentration of 10 μM treatment. Decreased 5-HT 2 agonist-induced head twitches in a dose-dependent manner. |
Animal Model: | 20-25 g 10-12 week old male C57Bl6 mice |
Dosage: | 5, 10 mg/kg |
Administration: | IP |