Synthesis and pharmacological characterisation of a series of compounds in which the oxime substructure present in imoproxifan was constrained in the pentatomic NO-donor furoxan ring, as well as their structurally related furazan analogues devoid of NO-donating properties, are described. The whole series of products displayed reversible histamine H3-antagonistic activity on guinea-pig ileum. 4-(4-(3-(1H-Imidazol-4-yl)propoxy)phenyl)furoxan-3-carbonitrile 16 was also able to induce partial relaxation when added to the bath after electrical contraction of the guinea-pig ileum during the study of its H3-antagonistic properties. This phenomenon seems to be dependent on NO-mediated sGC activation. The lipophilic–hydrophilic balance of all the products was investigated.

Furoxan analogues of the histamine H3-receptor antagonist imoproxifan and related furazan derivatives

TOSCO, Paolo;BERTINARIA, Massimo;DI STILO, Antonella;CENA, Clara;SORBA, Giovanni;FRUTTERO, Roberta;GASCO, Alberto
2005

Abstract

Synthesis and pharmacological characterisation of a series of compounds in which the oxime substructure present in imoproxifan was constrained in the pentatomic NO-donor furoxan ring, as well as their structurally related furazan analogues devoid of NO-donating properties, are described. The whole series of products displayed reversible histamine H3-antagonistic activity on guinea-pig ileum. 4-(4-(3-(1H-Imidazol-4-yl)propoxy)phenyl)furoxan-3-carbonitrile 16 was also able to induce partial relaxation when added to the bath after electrical contraction of the guinea-pig ileum during the study of its H3-antagonistic properties. This phenomenon seems to be dependent on NO-mediated sGC activation. The lipophilic–hydrophilic balance of all the products was investigated.
13(15)
4750
4759
http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4GBWJ8W-2&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=59f9e4a10f811b33af4e7656db656d9d
Histamine; H3-antagonists; furoxans; furazans
P. Tosco; M. Bertinaria; A. Di Stilo; C. Cena; G. Sorba; R. Fruttero; A. Gasco
File in questo prodotto:
File Dimensione Formato  
furoxan_analogues.pdf

Accesso riservato

Tipo di file: POSTPRINT (VERSIONE FINALE DELL’AUTORE)
Dimensione 297 kB
Formato Adobe PDF
297 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2318/23452
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 13
social impact