65248-65-9Relevant academic research and scientific papers
Synthesis of Water-Soluble Blue-Emissive Tricyclic 2-Aminopyridinium Salts by Three-Component Coupling-(3+3)-Anellation
Bakulina, Olga,Merkt, Franziska K.,Knedel, Tim-Oliver,Janiak, Christoph,Müller, Thomas J. J.
supporting information, p. 17240 - 17244 (2018/12/05)
The (3+3) anellation of alkynones and cyclic amidines is a novel and unexpected approach to generate intensively blue luminescent tricyclic 2-aminopyridinium salts with quantum yields Φf up to 63 % in water. By implementation into a consecutive three-component reaction, these title compounds are obtained rapidly and efficiently in a diversity-oriented fashion. Most interestingly, these bi- and tricyclic 2-aminopyridinium salts emit in dichloromethane and water solutions, thus making them interesting novel luminophore probes for bioanalytics, as well as in the solid state, thus making them blue emitters with tunable efficiency.
Benzylimidazolines as h5-HT(1B/1D) serotonin receptor ligands: A structure-affinity investigation
Law, Ho,Dukat, Malgorzata,Teitler, Milt,Lee, David K. H.,Mazzocco, Lucia,Kamboj, Raj,Rampersad, Vik,Prisinzano, Thomas,Glennon, Richard A.
, p. 2243 - 2251 (2007/10/03)
Benzylimidazolines may represent a class of 5-HT(1D) ligands that has yet to be exploited. On the basis of a previous report that the 2- (substituted-benzyl)imidazoline α-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT(1D) receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT(1D) (i.e., human 5- HT(1Dα)) receptors, this modification reduced h5-HT(1B) (i.e., human 5- HT(1Dβ)) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT(1B) binding than h5-HT(1D) binding. With the appropriate structural modifications, several compounds were identified that display 20- to > 100-fold selectivity for h5-HT(1D) versus h5-HT(1B) receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT(1D) agonists are currently being explored for their antimigraine action and that activation of h5-HT(1B) receptors might be associated with cardiovascular side effects, h5- HT(1D)selective agents may offer a new lead for the development of therapeutically efficacious agents.
1-(Phenylethynyl)aziridine in reactions with amines
Tikhomirov,Porchinskaya,Eremeev
, p. 498 - 501 (2007/10/02)
The reaction of 1-(phenylethynyl)aziridine with a primary or secondary amine gave 2-benzylimidazoline-2 or N-aminoethyl substituted phenylacetamidine via nucleophilic attack on the aziridine ring. The mechanism of aziridine ring opening by an amine was studied.
2-Alkylidenimidazolidine - Synthesis, Basicity, 1H- and 13C-NMR Spectra
Gruseck, Ursula,Heuschmann, Manfred
, p. 2053 - 2064 (2007/10/02)
4,5-Dihydroimidazolium salts 2, 3, and 4 were synthesized by carefully directed alkylation of 4,5-dihydroimidazoles 7 and 8. 2, 3, and 4 were deprotonated by sodium hydride to yield 2-alkylideneimidazolidines 1. 1H and 13C-NMR spectra allow to assign the
