PMID: 3012084Jun 1, 1986Paper

Indole-phenol bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analogue of labetalol

Journal of Medicinal Chemistry
A A AsselinC C Shaw


The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.


Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Xue-Mei Yang
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Xue-Mei Yang
Oct 11, 2017·Molecular Diversity·Jamatsing D RajputRatnamala S Bendre

Related Concepts

Antihypertensive Agents
Diastolic Blood Pressure
Dose-Response Relationship, Drug
Cavia porcellus
Pulse Rate
Hydrogen Bonding
Rats, Inbred SHR
Beta-adrenergic receptor
Structure-Activity Relationship

Related Feeds

Antihypertensive Agents: Mechanisms of Action

Antihypertensive drugs are used to treat hypertension (high blood pressure) which aims to prevent the complications of high blood pressure, such as stroke and myocardial infarction. Discover the latest research on antihypertensive drugs and their mechanism of action here.

Adrenergic Receptors: Trafficking

Adrenergic receptor trafficking is an active physiological process where adrenergic receptors are relocated from one region of the cell to another or from one type of cell to another. Discover the latest research on adrenergic receptor trafficking here.