3277-47-2

Upstream product

• 20494-43-3 N-Trimethylsilyl-O-phenyl-N'-cyan-isoharnstoff 
• 1122-85-6 phenyl cyanate 
• 79463-77-7 N-cyanodiphenylcarbonimidate 

Downstream Products

• 111970-99-1 C₁₂H₁₃N₃O₃ 
• 697299-77-7 N-cyano-N'-(3-{4-[3-Methyl-4-(6-methyl-pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)guanidine 
• 36335-91-8 2-chloro-4-methyl-6-phenoxy-[1,3,5]triazine 
• 80355-88-0 2-Chloro-4-chloromethyl-6-phenoxy-[1,3,5]triazine 
• 80355-87-9 2-Chloro-4-phenoxy-1,3,5-triazine 
• 78504-15-1 2-chloro-4-phenoxy-6-phenyl-1,3,5-triazine 

Relevant academic research and scientific papers

Design, synthesis, and: In vitro and in vivo characterization of 1-{4-[4-(substituted)piperazin-1-yl]butyl}guanidines and their piperidine analogues as histamine H3 receptor antagonists

Previously, we have shown that 1-substituted-[4-(7-phenoxyheptylpiperazin-1-yl)butyl]guanidine with electron withdrawing substituents at position 4 in the benzyl moiety exhibits high in vitro affinities toward the guinea pig jejunal histamine H3/sub

Synthesis and structure-activity relationships of cyanoguanidine-type and structurally related histamine H4 receptor agonists

Recently, we identified high-affinity human histamine H3 (hH3R) and H4 receptor (hH4R) ligands among a series of NG-acylated imidazolylpropylguanidines, which were originally designed as histamine H2 receptor (H2R) agonists. Aiming at selectivity for hH4R, the acylguanidine group was replaced with related moieties. Within a series of cyanoguanidines, 2-cyano-1-[4-(1H-imidazol-4-yl)butyl]-3-[(2-phenylthio)ethyl]guanidine (UR-PI376, 67) was identified as the most potent hH4R agonist (pEC50=7.47, α=0.93) showing negligible hH1R and hH2R activities and significant selectivity over the hH3R (pKB=6.00, α=-0.28), as determined in steady-state GTPase assays using membrane preparations of hHxR-expressing Sf9 cells. In contrast to previously described selective H4R agonists, this compound and other 3-substituted derivatives are devoid of agonistic activity at the other HR subtypes. Modeling of the binding mode of 67 suggests that the cyanoguanidine moiety forms chargeassisted hydrogen bonds not only with the conserved Asp-94 but also with the hH4R-specific Arg-341 residue. 2-Carbamoyl-1-[2-(1H-imidazol-4-yl)ethyl]-3-(3-phenylpropyl)guanidine (UR-PI97, 88) was unexpectedly identified as a highly potent and selective hH3R inverse agonist (pKB=8.42, >300-fold selectivity over the other HR subtypes). 2009 American Chemical Society.

One-Carbon Compounds as Synthetic Intermediates. The Synthesis of Hydropyrimidines and Hydroquinazolines by Sequential Nucleophilic Addition to Diphenyl Cyanocarbonimidate with Concomitant Cyclization

Diphenyl cyanocarbonimidate (1) undergoes nucleophilic addition with ω-amino esters and amines in a sequential manner to give guanidine derivatives that, for the most part, spontaneously cyclize to give hydropyrimidines or hydroquinazolines.The hydropyrimidines could be dehydrogenated to dihydropyrimidines, and the NCN group could be hydrolyzed to a carbonyl or amine group in the pyrimidine and to an amine group in the quinazoline series.The regiospecificity of the cyclization was determined by a combination of spectroscopic methods and comparison of compounds synthesized by standard routes.The scope of the synthetic route is indicated.Some of the acyclic N-cyano-O-phenylisoureas formed by the first nucleophilic addition exist as mixtures of isomers, and the barriers to interconversion have been determined by NMR spectroscopy.