Abstract
A series of azoles and aminoazoles with a 3,4-dichlorobenzyl moiety attached to a ring nitrogen atom was synthesized via reaction of the parent systems with 3,4-dichlorobenzyl chloride. Regioisomeric products were discriminated on the basis of 13C-NMR data or by NOE-difference spectroscopy. The affinities of some representatives towards sigma-1 and sigma-2 receptors were determined by receptor binding assays.
Highlights
Since their discovery in 1976 sigma receptors - initially proposed as a subtype of opioid receptor - and their physiological role have been investigated extensively; several reviews provide condensed information in this regard [I-61
In the course of a program dedicated to the development of more potent and, more selective sigma receptor ligands we synthesized a variety of compounds related to structure A [8].for instance, leaving the left part of the molecule unchanged, the saturated N-heterocyclic system in A was replaced by other heterocyclic and heteroaromatic moieties or even by longer carbon
We here report on the synthesis of various 3,4-dichlorobenzylazoles (Scheme 1) and their affinity towards sigma-I and sigma-2 receptors
Summary
Since their discovery in 1976 sigma receptors - initially proposed as a subtype of opioid receptor - and their physiological role have been investigated extensively; several reviews provide condensed information in this regard [I-61. In these cases clean separation of the regioisomers by column chromatography was not always possible or resulted in low yields of the pure compounds (mixed fractions predominating). I-(3,4-Dichlorobenzy1)-1H -pyrazole ( I ) The crude product was purified by column chromatography (silica gel, light petroleum - ethyl acetate 3:2) to afford 1.70 g (50%) of a yellowish oil which slowly solidified on standing to afford crystals of mp 31-32 "C.
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