cas 25379-26-4, 1-(TETRAHYDRO-2-FURYL)-3-(1-NAPHTHYL) PROPANE-2-CARBOXYLIC ACID | Articles data ｜lookchem

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25379-26-4

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Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor
Naftidrofuryl oxalate (Praxilene, 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (5-HT2) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT2A receptor, and the C-2′ configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT2A receptor that have clinical significance as vasodilators and CNS agents.
Hao, Jia,Chen, Bo,Yao, Yiwu,Hossain, Murad,Nagatomo, Takafumi,Yao, Hequan,Kong, Lingyi,Sun, Hongbin
p. 3441 - 3444
(2012/06/18)

Optical isomers of naftidrofuryl (=2-(diethylamino)ethyl 2-[(naphth-1-yl)methyl]-3-(tetrahydrofur-2-yl)propanoate)
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Descours,Festal,Leger,Carpy
p. 1757 - 1763
(2007/10/02)

2-DIETHYLAMINOETHYL ESTERS OF 1,3-DISUBSTITUTED PROPANE-2-CARBOXYLIC ACIDS
Alkaline hydrolysis of diethyl 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylate (IV) gave the crude acid V which was purified via the dipotassium salt and was obtained as the homogenous higher melting crystal form.Its thermic decarboxylation yielded the acid II as a mixture of two racemates (38:62); crystallization led to almost homogenous racemate B (10:90).Reaction of the sodium salt of II with dimethyl sulfate in methanol gave the methyl ester III which afforded by ester exchange with 2-diethylaminoethanol the ester I (mixture of two racemates 34:66). 2-Diethylaminoethyl 1,3-bis(1-naphthyl)propane-2-carboxylate (VII) was synthetized in three steps from diethyl (1-naphthylmethyl)malonate.Ester X was obtained from 1,3-bis(tetrahydro-2-furyl)propane-2-carboxylic acid by treatment with 2-diethylaminoethyl chloride in boiling 2-propanol in the presence of potassium carbonate.The acid V gave similarly the diester VI. 2-Diethylaminoethyl esters I, VI, VII, and X were transformed to the hydrogen oxalates.Pharmacological screening showed for the diester VI hypotensive, spasmolytic, antiarrhythmic, and antitussic activity.
Valenta, Vladimir,Holubek, Jiri,Svatek, Emil,Miller, Vladimir,Vlkova, Marie,Protiva, Miroslav
p. 2534 - 2544
(2007/10/02)

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Chemical Properties

Boiling Point: 464.2°C at 760 mmHg
Flash Point:169.1°C
Density: 1.183g/cm³
Solubility:DMSO (Slightly, Heated, Sonicated), Ethyl Acetate (Slightly)
Storage Temp.:Refrigerator, under inert atmosphere
Vapor Pressure: 2.04E-09mmHg at 25°C
PKA: 4.44±0.11(Predicted)
PSA: 46.53000
LogP: 3.65220

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