Document Detail

Synthesis and cardiovascular activity of metoprolol analogues.
MedLine Citation:
PMID:  14684326     Owner:  NLM     Status:  MEDLINE    
The synthesis of four novel analogues of metoprolol, a well-known beta1-blocker used to reduce arterial blood pressure, is described. The preparation of (2S,2'S)-7, (2R,2'S)-7, (2R,2'R)-8, and (2S,2'R)-8 was based on the reaction of racemic 2-[4-(2'-methoxyethyl)-phenoxymethyl]-oxirane (4) with (R)- or (S)-2-amino-1-butanol. Salient characteristics of analogues 7 and 8 relative to metoprolol are the incorporation of an additional stereogenic center, as well as a methyl group and a hydroxyl function on the nitrogen-containing chain. These novel derivatives present significant hypotensive and bradycardiac activity, although no blocking action toward beta1 and beta2 adrenergic receptor.
Roberto Melgar-Fernández; Patricia Demare; Enrique Hong; Miguel Angel Rosas; Jaime Escalante; Omar Muñoz-Muñiz; Eusebio Juaristi; Ignacio Regla
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  14     ISSN:  0960-894X     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2004 Jan 
Date Detail:
Created Date:  2003-12-19     Completed Date:  2004-08-27     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  191-4     Citation Subset:  IM    
Facultad de Estudios Superiores-Zaragoza, Universidad Nacional Autónoma de México, 09230 Mexico, D.F., México.
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MeSH Terms
Blood Pressure / drug effects*,  physiology
Calcium Chloride / pharmacology
Dose-Response Relationship, Drug
Heart Rate / drug effects*,  physiology
Metoprolol / analogs & derivatives*,  chemical synthesis*,  pharmacology
Muscle Contraction / drug effects
Muscle, Smooth, Vascular / drug effects,  physiology
Reg. No./Substance:
10043-52-4/Calcium Chloride; 37350-58-6/Metoprolol

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