Igel, Patrick and Schneider, Erich and Schnell, David and Elz, Sigurd and Seifert, Roland and Buschauer, Armin (2009) N(G)-Acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the N(G)-substituent. Journal of Medicinal Chemistry 52 (8), pp. 2623-2627.
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3-(1H-imidazol-4-yl)propylguanidine (SK&F 91486, 4) was identified as a potent partial agonist at the human histamine H3 receptor (hH3R) and human histamine H4 receptor (hH4R). With the aim to increase selectivity for the hH4R, the guanidine group in 4 was acylated. N1-Acetyl-N2-[3-(1H-imidazol-4-yl)propyl]guanidine (UR-PI288, 13) was a potent full agonist at hH4R (pEC50: 8.31, α: 1.00), possessing more than 1000- and 100-fold selectivity relative to hH1R and hH2R, respectively, and possessing only low intrinsic activity (α: 0.27) at hH3R.