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omega-Dialkylaminoalkyl Ethers of 6-(benzyl or phenyl)-1,3,3-trimethyl-2-oxabicyclo [2.2.2]octan-6-ol With Platelet Antiaggregating and Local Anesthetic Activities

omega-Dialkylaminoalkyl Ethers of 6-(benzyl or phenyl)-1,3,3-trimethyl-2-oxabicyclo [2.2.2]octan-6-ol With Platelet Antiaggregating and Local Anesthetic Activities

S Schenone, O Bruno, A Ranise, F Bondavalli, M L Cenicola, C Losasso, M Carnevale, R Ottavo, M D'Antonio

Farmaco. 1990 Dec;45(12):1309-25.

PMID: 2090141

Abstract:

The synthesis of 1,3,3-trimethyl-6-phenyl-2-oxabicyclo[2.2.2]octan-6-ol 2 and 6-benzyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol 3 starting from (+)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one and phenylmagnesium bromide or benzylmagnesium chloride, respectively, is described. Alcohols 2 and 3 gave a series of omega-dialkylaminoalkyl ethers 4 by reaction as sodium salts with omega-chloroalkyldialkylamines in toluene solution. Some compounds 4, in particular those derived from alcohol 2, showed a strong platelet antiaggregating activity in vitro, superior to that of acetylsalicylic acid, as well as in general an appreciable local anesthetic activity and a weak sedative effect in mice.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP100594	Phenylmagnesium chloride solution	100-59-4	Price
AP36637442	4-(2-Tetrahydro-2H-pyranoxy)phenylmagnesium bromide solution	36637-44-2	Price
AP6921342	Benzylmagnesium chloride solution	6921-34-2	Price

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