942-72-3Relevant articles and documents
Aminoguanidine hydrazone derivatives as non-peptide NPFF1 receptor antagonists reverse opioid induced hyperalgesia
Hammoud, Hassan,Elhabazi, Khadija,Quillet, Rapha?lle,Bertin, Isabelle,Utard, Valérie,Laboureyras, Emilie,Bourguignon, Jean-Jacques,Bihel, Frederic,Simonnet, Guy,Simonin, Frederic,Schmitt, Martine
, (2018/05/15)
Neuropeptide FF receptors (NPFF1R and NPFF2R) and their endogenous ligand Neuropeptide FF have been shown previously to display anti-opioid properties and to play a critical role in the adverse effects associated with chronic administrations of opiates including the development of opioid-induced hyperalgesia and analgesic tolerance. In this work, we sought to identify novel NPFF receptors ligands by focusing our interest on a series of heterocycles as rigidified non-peptide NPFF receptor ligands, starting from already described aminoguanidine hydrazones (AGH's). Binding experiments and functional assays highlighted AGH 1n and its rigidified analog 2-amino-dihydropyrimidine 22e for in vivo experiments. As earlier shown with the prototypical dipeptide antagonist RF9, both 1n and 22e reduced significantly the long lasting fentanyl-induced hyperalgesia in rodents. Altogether these data indicate that AGH rigidification maintains nanomolar affinities for both NPFF receptors, while improving antagonist character towards NPFF1R.
Strain-Promoted Reaction of 1,2,4-Triazines with Bicyclononynes
Horner, Katherine A.,Valette, Nathalie M.,Webb, Michael E.
supporting information, p. 14376 - 14381 (2015/10/05)
Strain-promoted inverse electron-demand Diels-Alder cycloaddition (SPIEDAC) reactions between 1,2,4,5-tetrazines and strained dienophiles, such as bicyclononynes, are among the fastest bioorthogonal reactions. However, the synthesis of 1,2,4,5-tetrazines is complex and can involve volatile reagents. 1,2,4-Triazines also undergo cycloaddition reactions with acyclic and unstrained dienophiles at elevated temperatures, but their reaction with strained alkynes has not been described. We postulated that 1,2,4-triazines would react with strained alkynes at low temperatures and therefore provide an alternative to the tetrazine cycloaddition reaction for use in in vitro or in vivo labelling experiments. We describe the synthesis of a 1,2,4-triazin-3-ylalanine derivative fully compatible with the fluorenylmethyloxycarbonyl (Fmoc) strategy for peptide synthesis and demonstrate its reaction with strained bicyclononynes at 37°C with rates comparable to the reaction of azides with the same substrates. The synthetic route to triazinylalanine is readily adaptable to late-stage functionalization of other probe molecules, and the 1,2,4-triazine-SPIEDAC therefore has potential as an alternative to tetrazine cycloaddition for applications in cellular and biochemical studies.
1H- and 13C-NMR investigations on σ-adduct formation of 1,2,4-triazine 4-oxides and 3-chloro-6-phenyl-1,2,4-triazine with liquid ammonia and alkylamines
Rykowski, Andrzej,Chupakhin, Oleg N.,Kozhevnikov, Dmitry N.,Kozhevnikov, Valery N.,Rusinov, Vladimir L.,Van Der Plas, Henk C.
, p. 127 - 133 (2007/10/03)
1H- and 13C-NMR spectra of the σ-adducts formed between 6-phenyl-1,2,4-triazine 4-oxide (1a), 3-ethyl-6-phenyl-1,2,4-triazine 4-oxide (1b) and liquid ammonia, methylamine or dimethylamine are described, together with 1H NM
