ChemInform Abstract: ANTIARRHYTHMIC ACTIVITY OF P‐HYDROXY‐N‐(2‐DIETHYLAMINOETHYL)BENZAMIDE (THE P‐HYDROXY ISOSTERE OF PROCAINAMIDE) IN DOGS AND MICE
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Procainamide
Benzamide
Isostere
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAntiarrhythmic activity of p-hydroxy-N-(2-diethylaminoethyl)benzamide (the p-hydroxy isostere of procainamide) in dogs and miceDennis E. Drayer, Barry H. Slaven, Marcus M. Reidenberg, Ervin E. Bagwell, and Maria CordovaCite this: J. Med. Chem. 1977, 20, 2, 270–274Publication Date (Print):February 1, 1977Publication History Published online1 May 2002Published inissue 1 February 1977https://pubs.acs.org/doi/10.1021/jm00212a017https://doi.org/10.1021/jm00212a017research-articleACS PublicationsRequest reuse permissionsArticle Views88Altmetric-Citations3LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
Benzamide
Procainamide
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Therapeutical efficacy was clinically evaluated in 21 patients with ventricular cardiac arrhythmias. The drug was given orally with preceded intramuscular dose. Therapeutic effect was verified by the measurements of procainamide and N-acetylprocainamide concentrations in blood serum to determine the minimal effective concentration of the drug required to obtain satisfactory antiarrhythmic effect. Procainamide proved effective in cardiac arrhythmias in 14 patients (66.7%) with statistical significance in the acute myocardial infarctions; blood serum procainamide plus N-acetylprocainamide levels being were below the therapeutical range. The poor correlation of the dose of the drug and respective procainamide, N-acetylprocainamide concentrations in blood was observed. Relationship of the therapeutical effects blood serum level of the drug should be estimated basing of the assays of both procainamide and N-acetylprocainamide .
Procainamide
Therapeutic index
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l,l-Type and l,d-type (E)-alkene dipeptide isosteres (EADIs) that have unnatural side chains at the α-position were synthesized by the combination of stereoselective aziridinyl ring-opening reactions and organozinc−copper-mediated anti-SN2' reactions toward a single substrate of γ,δ-cis-γ,δ-epimino (E)-α,β-enoate. The utility of this methodology was demonstrated by the stereoselective synthesis of a set of diastereomeric EADIs of l-Arg-l/d-3-(2-naphthyl)alanine (Nal) that is contained in a small CXCR4 antagonist FC131 [cyclo(-d-Tyr-Arg-Arg-Nal-Gly-)]. Furthermore, a (Nal-Gly)-type EADI was synthesized by samarium diiodide (SmI2)-induced reduction of a γ-acetoxy-α,β-enoate. Several FC131 analogues, in which these EADIs were inserted for reduction of their peptide character, were synthesized with analogues containing reduced amide-type dipeptide isosteres to investigate the importance of these amide bonds for anti-HIV and CXCR4-antagonistic activity.
Alkene
Diastereomer
Amide
Isostere
Peptide Synthesis
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Moiety
Benzamide
Structure–activity relationship
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Isostere
Structure–activity relationship
Docking (animal)
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Benzamide
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Human immunodeficiency virus type 1 (HIV-1) protease inhibitors containing four types of hydroxyethylene dipeptide isosteres were designed and synthesized. These inhibitors consist of eight stereoisomers of phenylalanylproline (Phe-psi[H.E.]-Pro), four stereoisomers of phenylalanylalanine [Phe-psi[H.E.]-Ala), and one stereoisomer each of phenylalanylglycine (Phe-psi[H.E.]-Gly) and cyclohexylalanylalanine (Cha-psi[H.E.]-Ala) hydroxyethylene dipeptide isosteres. For the synthesis of the latter two isosteres, a newly developed synthetic method for gamma-lactone was applied. The inhibitory activities of these peptides were evaluated by cleavage assay of partially purified gag proteins or purified synthetic peptide. Of the inhibitors examined, compounds 2c (Z-Asn-(2S,3R,4S,5S)-Phe-psi[H.E.]-Pro-NHB(un); Bu(n) = n-butyl, Ki = 0.50 microM), 21a (Z-Asn-(2R,4S,5S)-Phe-psi[H.E.]-Ala- NHBu(n), Ki = 0.34 microM) and 23 (Z-Asn-(2R,4S,5S)-Cha-psi[H.E.]-Ala- NHBu(n), Ki = 0.46 microM) were moderately potent inhibitors. The results revealed that the alkyl substituent at C2 is essential, and the stereochemistry of the hydroxyethylene dipeptide isosteres greatly affected their inhibitory activities.
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Isostere
Amide
Peptide bond
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Tetrapeptide
Diastereomer
Isostere
Phosphonate
Amide
Moiety
Reactivity
Pancreatic elastase
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