Ak. Sinha et al., SYNTHESIS OF OXIME ETHER DERIVATIVES OF BETA-ARYLPROPIOPHENONES AND 2-P-METHOXYBENZYLINDAN-1-ONE AS POTENTIAL ANTIINFLAMMATORY AND ANTIULCER AGENTS, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 32(7), 1993, pp. 738-745
Condensation of the epoxypropyl ethers 7-9 and 29, obtained by epoxypr
opylation of beta-arylpropiophenone oximes (4-6) and p-methoxybenzylin
danone oxime (28), with sodium azide or amines furnishes 3-azido or am
ino-2-hydroxypropyl ethers (10-22 and 30-32). Treatment of the oxime 8
with sodium methoxide gives 3-methoxy-2-hydroxypropyl ether (26). Alk
ylation of 4, 5 and 28 with pyrrolidinoethyl/phenylpiperazinylpropyl c
hlorides affords the corresponding omega-aminoalkyloximino derivatives
(13-25, 33 and 34). Amongst the compounds tested, 30 and 31 show 80%
and 50% antiulcer activity respectively at 10 mg/kg dose and compounds
13-16 and 21 exhibit antiinflammatory activity in rats against the ca
rrageenin-induced oedema.