Document Report Card

ID: ALA1124112

Journal: J Med Chem

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

Authors: Fagan GP, Chapleo CB, Lane AC, Myers M, Roach AG, Smith CF, Stillings MR, Welbourn AP.

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 antagonist/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.

CiteXplore: 2896247

DOI: 10.1021/jm00400a009