Biomaterial Database

Synthesis and beta-adrenergic antagonist activity of heterocyclic propanolamines. 1993

D Vo, and M W Wolowyk, and E E Knaus

Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Canada.

The synthesis and beta-adrenergic antagonist activities of a group of 1-(heteroaryloxy)- and 1-(heteroaryl)-3-alkylamino-2-propanols is described. beta 1-Adrenolytic (atria) structure-activity correlations indicated that replacement of the 1-naphthyl moiety of propranolol by a 4-quinolyl- (10), 2-quinolyl- (24), or 2-pyrimidyl- (26) heterocyclic moiety resulted in a 10-16 fold reduction in activity. The 1-(4-quinolyloxy)- (10) and 1-(2-quinolyloxy)- (24-25) heteroaryl moieties provided more potent activity than the structurally related 1-[2-(2H-isoquinolin-1-one)]- (31-32) or 1-[3-(3H-quinazolin-4-one)]- (35-36) moieties. All compounds tested exhibited weak beta 2-adrenolytic activity on trachea. Although the most potent beta 1-antagonist, 1-(2-pyrimidyloxy)-3-isopropylamino-2-propanol (26), was 13-fold less potent than metoprolol, it exhibited a beta 1/beta 2 selectivity ratio superior to the cardioselective metoprolol.

UI	MeSH Term	Description	Entries
D008790	Metoprolol	A selective adrenergic beta-1 blocking agent that is commonly used to treat ANGINA PECTORIS; HYPERTENSION; and CARDIAC ARRHYTHMIAS.	Beloc-Duriles,Betaloc,Betaloc-Astra,Betalok,CGP-2175,H 93-26,Lopressor,Metoprolol CR-XL,Metoprolol Succinate,Metoprolol Tartrate,Seloken,Spesicor,Spesikor,Toprol,Toprol-XL,Beloc Duriles,Betaloc Astra,CGP 2175,CGP2175,H 93 26,H 9326,Metoprolol CR XL,Toprol XL
D011412	Propanolamines	AMINO ALCOHOLS containing the propanolamine (NH2CH2CHOHCH2) group and its derivatives.	Aminopropanols
D006168	Guinea Pigs	A common name used for the genus Cavia. The most common species is Cavia porcellus which is the domesticated guinea pig used for pets and biomedical research.	Cavia,Cavia porcellus,Guinea Pig,Pig, Guinea,Pigs, Guinea
D006571	Heterocyclic Compounds	Cyclic compounds that include atoms other than carbon in their ring structure.	Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D000319	Adrenergic beta-Antagonists	Drugs that bind to but do not activate beta-adrenergic receptors thereby blocking the actions of beta-adrenergic agonists. Adrenergic beta-antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches, and anxiety.	Adrenergic beta-Antagonist,Adrenergic beta-Receptor Blockader,Adrenergic beta-Receptor Blockaders,beta-Adrenergic Antagonist,beta-Adrenergic Blocker,beta-Adrenergic Blocking Agent,beta-Adrenergic Blocking Agents,beta-Adrenergic Receptor Blockader,beta-Adrenergic Receptor Blockaders,beta-Adrenoceptor Antagonist,beta-Blockers, Adrenergic,beta-Adrenergic Antagonists,beta-Adrenergic Blockers,beta-Adrenoceptor Antagonists,Adrenergic beta Antagonist,Adrenergic beta Antagonists,Adrenergic beta Receptor Blockader,Adrenergic beta Receptor Blockaders,Adrenergic beta-Blockers,Agent, beta-Adrenergic Blocking,Agents, beta-Adrenergic Blocking,Antagonist, beta-Adrenergic,Antagonist, beta-Adrenoceptor,Antagonists, beta-Adrenergic,Antagonists, beta-Adrenoceptor,Blockader, Adrenergic beta-Receptor,Blockader, beta-Adrenergic Receptor,Blockaders, Adrenergic beta-Receptor,Blockaders, beta-Adrenergic Receptor,Blocker, beta-Adrenergic,Blockers, beta-Adrenergic,Blocking Agent, beta-Adrenergic,Blocking Agents, beta-Adrenergic,Receptor Blockader, beta-Adrenergic,Receptor Blockaders, beta-Adrenergic,beta Adrenergic Antagonist,beta Adrenergic Antagonists,beta Adrenergic Blocker,beta Adrenergic Blockers,beta Adrenergic Blocking Agent,beta Adrenergic Blocking Agents,beta Adrenergic Receptor Blockader,beta Adrenergic Receptor Blockaders,beta Adrenoceptor Antagonist,beta Adrenoceptor Antagonists,beta Blockers, Adrenergic,beta-Antagonist, Adrenergic,beta-Antagonists, Adrenergic,beta-Receptor Blockader, Adrenergic,beta-Receptor Blockaders, Adrenergic
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships