Indoline analogs of idazoxan: potent .alpha.2-antagonists and .alpha.1-agonists

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Abstract
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 antaogonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 analogues; however, this .alpha.2-antagonism is often accompanied by .alpha.1-agonist activity. It was not possible to separate .alpha.2-antagonist from .alpha.1-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 .alpha.2-antagonists and .alpha.1-agonists. Substitution at the 4- and 7-position of the indoline ring generally gave compounds with nonselective agonist properties.