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Acylguanidines as bioisosteres of guanidines: N(G)-acylated imidazolylpropylguanidines, a new class of histamine H2 receptor agonists

Ghorai, Prasanta and Kraus, Anja and Keller, Max and Götte, Carsten and Igel, Patrick and Schneider, Erich and Schnell, David and Bernhardt, Günther and Dove, Stefan and Zabel, Manfred and Elz, Sigurd and Seifert, Roland and Buschauer, Armin (2008) Acylguanidines as bioisosteres of guanidines: N(G)-acylated imidazolylpropylguanidines, a new class of histamine H2 receptor agonists. Journal of Medicinal Chemistry 51 (22), pp. 7193-7204.

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Other URL: http://pubs.acs.org/cgi-bin/asap.cgi/jmcmar/asap/html/jm800841w.html, http://pubs.acs.org/cgi-bin/asap.cgi/jmcmar/asap/pdf/jm800841w.pdf


Abstract

N(1)-Aryl(heteroaryl)alkyl-N(2)-[3-(1H-imidazol-4-yl)propyl]guanidines are potent histamine H2-receptor (H2R) agonists, but their applicability is compromised by the lack of oral bioavailability and CNS penetration. To improve pharmacokinetics, we introduced carbonyl instead of methylene adjacent to the guanidine moiety, decreasing the basicity of the novel H2R agonists by 4-5 orders of ...

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Item Type:Article
Date:25 October 2008
Institutions:Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer)
Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry I (Prof. Elz)
Chemistry and Pharmacy > Institute of Pharmacy > Pharmacology and Toxicology (Prof. Schlossmann, formerly Prof. Seifert)
Projects:GRK 760, Graduiertenkolleg Medizinische Chemie
Identification Number:
ValueType
18950149PubMed ID
10.1021/jm800841wDOI
Related URLs:
URLURL Type
http://pubs.acs.org/subscribe/journals/jmcmar/suppinfo/jm800841w/jm800841w-File002.pdfSupplementary Material
Keywords:bioisoterism; histamine receptors; H2 receptor agonist; H2 receptor model; H4 receptor agonist; acylguanidine; arpromidine
Dewey Decimal Classification:500 Science > 570 Life sciences
500 Science > 540 Chemistry & allied sciences
500 Science > 500 Natural sciences & mathematics
Status:Published
Refereed:Yes, this version has been refereed
Created at the University of Regensburg:Yes
Deposited On:29 Oct 2008 21:03
Last Modified:05 Aug 2009 13:48
Item ID:4683
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