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Indoline Analogues of Idazoxan: Potent alpha2-Antagonists and alpha1-Agonists
The synthesis and alpha-adrenergic activity of a series of substituted 2-imidazolinylindolines are described.Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent.Many of the derivatives possess greater presynaptic antagonist potency that the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this alpha2-antagonism is often accompanied by alpha1-agonist activity.It was not possible to separate alpha2-antagonist from alpha1-agonist properties in this series.Compounds of most interest proved to be the N-ethyl 6, 5-chloro-N-methyl 18 and 5-chloro-N-ethyl 23 derivatives, all being potent alpha2-antagonists and alpha1-agonists.Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.
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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles