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ChemicalBook--->CAS DataBase List--->53597-27-6

53597-27-6

53597-27-6 Structure

53597-27-6 Structure
IdentificationMore
[Name]

Fendosal
[CAS]

53597-27-6
[Synonyms]

5-(4,5-dihydro-2-phenyl-3h-benz[e]indol-3-yl)salicylic acid
FENDOSAL
3-(3-carboxy-4-hydroxyphenyl)-2-phenyl-4,5-dihydro-3h-benz(e)indole
5-(4,5-dihydro-2-phenyl-3h-benz(e)indol-3-yl)-2-hydroxy-benzoicaci
5-(4,5-dihydro-2-phenyl-3h-benz(e)indol-3-yl)-2-hydroxybenzoicacid
alnovin
hp129
Fendozal
P 71-0129
[Molecular Formula]

C25H19NO3
[MDL Number]

MFCD00866078
[Molecular Weight]

381.42
[MOL File]

53597-27-6.mol
Chemical PropertiesBack Directory
[Melting point ]

223-225° (dec)
[Boiling point ]

508.82°C (rough estimate)
[density ]

1.2182 (rough estimate)
[refractive index ]

1.6000 (estimate)
[pka]

2.40±0.10(Predicted)
[CAS DataBase Reference]

53597-27-6(CAS DataBase Reference)
Hazard InformationBack Directory
[Originator]

Alnovin,Hoechst
[Uses]

Anti-inflammatory.
[Definition]

ChEBI: Fendosal is a benzoindole that is 4,5-dihydro-3H-benzo[e]indole in which the nitrogen is substituted by a 3-carboxy-4-hydroxyphenyl group. A non-narcotic analgesic and non-steroidal anti-inflammatory drug, it has greater analgesic and inflammatory responses than aspirin but with less gastrointestinal toxicity. It has a role as a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is a member of pyrroles, a benzoindole and a monohydroxybenzoic acid.
[Manufacturing Process]

To a stirred refluxing solution of 20.2 g (0.1 mole) of 1-(1-pyrrolidino)-3,4- dihydronaphthalene and 50 ml of toluene was added dropwise during 30 minutes under nitrogen a solution of 20.1 g (0.1 mole) of phenacyl bromide in 65 ml of dry toluene. The mixture was heated under reflux for 6 hours, diluted with 50 ml of water, refluxed for 4 hours, and cooled. The layers were separated and the aqueous phase was extracted with benzene. The organic solution was dried over sodium sulfate and concentrated to a semi-solid. Trituration with cold 30°-60° petroleum ether gave 23.6 g (78%) of solid, 2- phenacyl-1-tetralone, MP: 73°-76°C. Recrystallization from 60°-90° petroleum ether raised the melting point to 87°-88°C.
A mixture of 20.0 g (0.076 mole) of 2-phenacyl-1-tetralone, 11.6 g (0.076 mole) of 5-aminosalicyclic acid, and 70 ml of glacial acetic acid was heated under reflux for 4 hours, cooled, diluted with 10 ml of water and filtered. The filter cake was washed with water and dried to provide 15.5 g of solid, 5-(4,5- dihydro-2-phenyl-3H-benz[e]indol-3-yl)-2-hydroxy-benzoic acid. MP: 215°- 218°C. Recristallization from benzene-cyclohexane gave 6.5 g (22%) of yellow crystals, MP: 245°-247°C.
[Brand name]

Alnovin(Hoechst-Roussel).
[Therapeutic Function]

Analgesic, Antiinflammatory, Antipyretic
Safety DataBack Directory
[Toxicity]

LD50 in mice, rats, rabbits (mg/kg): 740, 450, 560 orally; in mice (mg/kg): 510 i.p. (Lassman)
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