Efaroxan is an
α2-adrenergic receptor antagonist
An antagonist is a character in a story who is presented as the chief foe of the protagonist.
Etymology
The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...
and
antagonist
An antagonist is a character in a story who is presented as the chief foe of the protagonist.
Etymology
The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...
of the
imidazoline receptor Imidazoline receptors are the primary receptors on which clonidine and other imidazolines act. There are three main classes of imidazoline receptor: I1 is involved in inhibition of the sympathetic nervous system to lower blood pressure, I2 has as ye ...
.
Synthesis
![Efaroxan synthesis](https://upload.wikimedia.org/wikipedia/commons/c/c6/Efaroxan_synthesis.svg)
The
Darzens reaction
The Darzens reaction (also known as the Darzens condensation or glycidic ester condensation) is the chemical reaction of a ketone or aldehyde with an α- haloester in the presence of a base to form an α,β-epoxy ester, also called a "glycidic es ...
between 2-fluorobenzaldehyde
7848-46-1(1) and Ethyl 2-bromobutyrate
33-68-6(2) gives ethyl 2-ethyl-3-(2-fluorophenyl)oxirane-2-carboxylate
CID:100942311(3). A catalytic hydrogenation over Pd/C would give ethyl 2-
2-fluorophenyl)methyl2-hydroxybutanoate
CID:77591056(4).
Saponification
Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...
of the ester then gives 2-
2-Fluorophenyl)methyl2-hydroxybutanoic acid
CID:53869347(5). Treatment with 2 molar equivalents of
sodium hydride
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in co ...
apparently gives 2-Ethyl-2,3-dihydrobenzofuran-2-carboxylic acid
11080-50-3(6). Treatment of the carboxylic acid with
thionyl chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...
then gives the acid chloride and subsequent treatment of this with
ethylenediamine
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...
in the presence of trimethylaluminium completed the synthesis of ' (8).
See also
*
Fluparoxan
Fluparoxan (developmental code name GR50360A) is a potent α2-adrenergic receptor antagonist (pKB = 7.9) with excellent selectivity for this receptor over the α1-adrenergic receptor (2,630-fold), and is the only well-studied α2-adrenergic rec ...
*
Idazoxan
Idazoxan (INN) is a drug which is used in scientific research. It acts as both a selective α2 adrenergic receptor antagonist, and an antagonist for the imidazoline receptor. Idazoxan has been under investigation as an antidepressant, but it did ...
References
External links
*
Benzofurans
Imidazolines
Alpha-2 blockers
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