The synthesis of 1,3,3-trimethyl-5-endo-(1-piperidinyl)- and -5-endo-(4-morpholinyl)-2-oxabicyclo[2.2.2]octan-6-hydroxyimine I and II starting from 5-endo-bromo-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimine and excess piperidine or morpholine is described. I and II gave a series of ω-dialkylaminoalkyl ethers (III, R1 = alkyl or NR2 = heterocyclic amine; n = 2 or 3) by reaction as Na salts with ω-chloroalkyldialkylamines in DMF soln. Some of III showed in mice an appreciable antiarrhythmic and local anesthetic activity, as well as a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid.
ω-Dialkylaminoalkyl ethers of 5-endo-dialkylamino-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimines with platelet antiaggregating, antiarrhythmic and local anesthetic activities
SCHENONE, SILVIA;RANISE, ANGELO;BRUNO, OLGA;BONDAVALLI, FRANCESCO;
1990-01-01
Abstract
The synthesis of 1,3,3-trimethyl-5-endo-(1-piperidinyl)- and -5-endo-(4-morpholinyl)-2-oxabicyclo[2.2.2]octan-6-hydroxyimine I and II starting from 5-endo-bromo-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-hydroxyimine and excess piperidine or morpholine is described. I and II gave a series of ω-dialkylaminoalkyl ethers (III, R1 = alkyl or NR2 = heterocyclic amine; n = 2 or 3) by reaction as Na salts with ω-chloroalkyldialkylamines in DMF soln. Some of III showed in mice an appreciable antiarrhythmic and local anesthetic activity, as well as a platelet antiaggregating activity in vitro comparable to that of acetylsalicylic acid.
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