99064-98-9Relevant academic research and scientific papers
Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/[n-Bu4N]OCN as a useful system for the efficient conversion of tetrahydropyranyl (THP) ethers to the corresponding alkyl isocyanates
Akhlaghinia, Batool,Samiei, Sima
experimental part, p. 2525 - 2529 (2010/03/31)
Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium cyanate was used as an efficient system for the conversion of tetrahydropyranyl ethers to the corresponding alkyl isocyanates. Taylor & Francis Group, LLC.
Histamine H3 and H4 receptor affinity of branched 3-(1H-imidazol-4-yl)propyl N-alkylcarbamates
?azewska, Dorota,Wiecek, Ma?gorzata,Ligneau, Xavier,Kottke, Tim,Weizel, Lilia,Seifert, Roland,Schunack, Walter,Stark, Holger,Kie?-Kononowicz, Katarzyna
scheme or table, p. 6682 - 6685 (2010/06/16)
A series of imidazole-containing (non-)chiral carbamates were tested at human histamine H3 receptor (H3R). All compounds displayed Ki values below 100 nM. A trend for a stereoselectivity at human H3R was observed for the chiral α-branched ligands. Selected compounds were also tested at human histamine H4 receptor and showed moderate to weak affinities (118-1460 nM).
A new and convenient method of generating alkyl isocyanates from alcohols, thiols and trimethylsilyl ethers using triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone/Bu4NOCN
Akhlaghinia, Batool
, p. 1955 - 1958 (2007/10/03)
Alkyl isocyanates are prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with triphenylphosphine/2,3-dichloro- 5,6-dicyanobenzoquinone/ Bu4NOCN in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl isocyanates in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers. Georg Thieme Verlag Stuttgart.
Development of chiral N-alkylcarbamates as new leads for potent and selective H3-receptor antagonists: Synthesis, capillary electrophoresis, and in vitro and oral in vivo activity
Sasse, Astrid,Kiec-Kononowicz, Katarzyna,Stark, Holger,Motyl, Malgorzata,Reidemeister, Sibylle,Ganellin, C. Robin,Ligneau, Xavier,Schwartz, Jean-Charles,Schunack, Walter
, p. 593 - 600 (2007/10/03)
Novel carbamates as derivatives of 3-(1H-imidazol-4-yl)propanol with an N-alkyl chain were prepared as histamine H3-receptor antagonists. Branching of the N-alkyl side chain with methyl groups led to chiral compounds which were synthesized stereospecifically by a Mitsunobu protocol adapted Gabriel synthesis. The optical purity of some of the chiral compounds was determined (ee > 95%) by capillary electrophoresis (CE). The investigated compounds showed pronounced to high antagonist activity (K(i) values of 4.1-316 nM) in a functional test for histamine H3 receptors on rat cerebral cortex synaptosomes. Similar H3-receptor antagonist activities were observed in a peripheral model on guinea pig ileum. No stereoselective discrimination for the H3 receptor for the chiral antagonists was found with the in vitro assays. All compounds were also screened for central H3-receptor antagonist activity in vivo in mice after po administration. Most compounds were potent agents of the H3-receptor-mediated enhancement of brain N(τ)- methylhistamine levels. The enantiomers of the N-2-heptylcarbamate showed a stereoselective differentiation in their pharmacological effect in vivo (ED50 of 0.39 mg/kg for the (S)-derivative vs 1.5 mg/kg for the (R)- derivative) most probably caused by differences in pharmacokinetic parameters. H1- and H2-receptor activities were determined for some of the novel carbamates, demonstrating that they have a highly selective action at the histamine H3 receptor.
