1.
Chirality
; 2(4): 280-3, 1990.
Article
in English
| MEDLINE
| ID: mdl-2083151
ABSTRACT
The title compound (+/-)-1 (CN-100) was efficiently resolved into a pair of enantiomers by fractional crystallization of the diastereomeric salts of (-)- and (+)-phenylethylamine. The purity of the enantiomers was determined using the chiral cellulose column (CHIRALCEL OJ) which was allowed direct separation of the enantiomers. A separation factor (alpha) of 1.73 was obtained. X-Ray crystallographic analysis of the (+)-isomer [salt of (-)-1-(4-bromophenyl)ethylamine] showed that this enantiomer has S-configuration. Biological studies have shown that only the (+)-isomer has antiinflammatory activity. Racemizaiton of (-)-isomer was carried out by heating its propionic acid solution in the presence of mineral acid, such as HBr.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/chemistry , Benzothiepins/chemistry , Animals , Benzothiepins/isolation & purification , Benzothiepins/therapeutic use , Dogs , Edema/chemically induced , Edema/drug therapy , Models, Molecular , Molecular Structure , Stereoisomerism , Structure-Activity Relationship , X-Ray Diffraction
2.
J Agric Food Chem
; 19(2): 372-4, 1971.
Article
in English
| MEDLINE
| ID: mdl-5546168