| Synthesis and adrenergic beta-blocking activity of ortho-, meta- and para-oxypropanolamino-substituted [(benzylideneamino)oxy]propanolamines. | |
| | |
MedLine Citation:
|
PMID: 7669168 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
The N-isopropyl- and N-t-butyl-substituted 1-[o-(3-amino-2-hydroxypropoxy)benzylideneaminoxy]-3-amino-2-propa nols (7a,b) and their meta (8a,b) and para (9a,b) isomers, in which a single aromatic ring is substituted both by the oxypropanolaminic chain of (aryloxy)propanolaminic beta-adrenergic antagonists (AOPAs) and the [(methyleneamino)oxy]propanolaminic chain of [(methyleneamino)oxy]-propanolaminic beta-blocking drugs (MAOPAs), were synthesized and assayed for their beta-adrenergic activity by functional tests on isolated preparations. Compounds 7-9 represent a new type of molecular duplication of beta-adrenergic drugs, formally deriving from the sharing of the aromatic portions of two different pharmacophoric subunits, namely the (aryloxy)propanolaminic portion of AOPAs and the [(benzylideneamino)oxy]propanolaminic portion of aryl-substituted MAOPAs. The pharmacological results showed that the beta-blocking activity of compounds 7-9 is closely related to the way in which the two subunits are linked by the aromatic nucleus: the activity decreases on passing from the ortho-compounds (7a,b) to the meta (8a,b) and then to the para (9a,b) isomers. A comparison of this activity trend with those found for series of both beta-blocking AOPAs and aryl-substituted MAOPAs seems to indicate that compounds 7-9 can be considered more as AOPAs substituted on the phenyl ring by a [(methyleneamino)oxy]propanolaminic chain rather than as aromatic MAOPAs substituted on the same phenyl moiety by an oxypropanolaminic portion. |
| | |
Authors:
|
A Balsamo; A Lapucci; B Macchia; M Macchia; E Orlandini; A Rossello; G Ferni; M Pinza |
Related Documents
:
|
18817398 - Synthesis and reactions of a stable 1,2-diaryl-1,2-dibromodisilene: a precursor for sub... 17945208 - Synthesis, cytotoxicity, and hemolytic activity of 6'-o-substituted dioscin derivatives. 22799088 - Isolation of antitrypanosomal compounds from vitis repens, a medicinal plant of myanmar. 16496968 - Theoretical study on the lithium-halogen exchange reaction of 1,1-dihaloalkenes with me... 3146978 - Chemical and enzymic oxidation by tyrosinase of 3,4-dihydroxymandelate. 2673948 - Biological interactions of alpha,beta-unsaturated aldehydes. |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: Farmaco (Società chimica italiana : 1989) Volume: 50 ISSN: 0014-827X ISO Abbreviation: Farmaco Publication Date: 1995 Apr |
Date Detail:
|
Created Date: 1995-10-18 Completed Date: 1995-10-18 Revised Date: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 8912641 Medline TA: Farmaco Country: ITALY |
Other Details:
|
Languages: eng Pagination: 239-43 Citation Subset: IM |
Affiliation:
|
Dipartimento di Scienze Farmaceutiche, Università di Pisa, Italy. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Adrenergic beta-Antagonists
/
chemical synthesis*,
pharmacology Animals Guinea Pigs Heart Atria Male Molecular Conformation Myocardial Contraction / drug effects Propanolamines / chemistry*, pharmacology Trachea |
| Chemical | |
Reg. No./Substance:
|
0/Adrenergic beta-Antagonists; 0/Propanolamines |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Antifungal agents. 10. Synthesis and antifungal activities of aryl-(1H-imidazol-1-yl)-(isoquinolin-1...
Next Document: Leaf extracts of some Cordia species: analgesic and anti-inflammatory activities as well as their ch...