4361-38-0Relevant articles and documents
Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine h2 receptor agonists
Ghorai, Prasanta,Kraus, Anja,Keller, Max,G?tte, Carsten,Igel, Patrick,Schneider, Erich,Schnell, David,Bernhardt, Günther,Dove, Stefan,Zabel, Manfred,Elz, Sigurd,Seifert, Roland,Buschauer, Armin
supporting information; experimental part, p. 7193 - 7204 (2009/10/02)
N1-Aryl(heteroaryl)alkyl-N2-[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 magnitude. Some acylguanidines with one phenyl ring were even more potent than their diaryl analogues. As demonstrated by HPLC-MS, the acylguanidines (bioisosteres of the alkylguanidines) were absorbed from the gut of mice and detected in brain. In GTPase assays using recombinant receptors, acylguanidines were more potent at the guinea pig than at the human H2R. At the hH1R and hH3R, the compounds were weak to moderate antagonists or partial agonists. Moreover, potent partial hH4R agonists were identified. Receptor subtype selectivity depends on the imidazolylpropylguanidine moiety (privileged structure), opening an avenue to distinct pharmacological tools including potent H4R agonists.
Nickelalactone als Synthesebausteine: Sonochemische und Bimetallsktivierung der Kreuzkopplungsreaction mit Alkyl-halogeniden
Fischer, Reinald,Walther, Dirk,Braeunlich, Gabriele,Undeutsch, Bernd,Ludwig, Werner
, p. 395 - 407 (2007/10/02)
Nickelalactones with five- and six-membered chelate ring structures can be synthesized in a simple one-pot reaction, starting from Ni(acac)2, bipy, Et3Al and cyclic anhydrides.In the presence of MnI2 and by activation with ultrasound they react selectively with alkyl iodides in cross coupling reactions.The reason for the activating effect of MnI2 is the formation of bimetallic complexes.Many reactive functional groups (e.g.COOR, CHO, CN) can be tolerated.Therefore the cross coupling reaction is of preparative value in the synthesis of functionalized carboxylic acids.
Asymmetric hydrogenation of β - methylcinnamates of phenylalkylmethanols. Catalyst-phenyl groups interactions in the preferred adsorption conformation
Gallina, Carlo,Lucente, Gino,Pinnen, Francesco
, p. 2361 - 2363 (2007/10/06)
The β-methylcinnamates of four S-alkylphenylmethanols have been hydrogenated on Pt catalyst. The observed asymmetric inductions suggest that simultaneous bonded interactions of both the phenyl groups with the catalyst in the transition states do not occur.
