- Tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA) as a highly fluorescent Zn2+ probe prepared by convenient C3-symmetric tripodal amine synthesis
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A convenient synthesis of C3-symmetric tribenzylamine (TBA) derivatives has been investigated. The reaction of benzyl chlorides with acetaldehyde ammonia trimer (1) in the presence of base afforded tribenzylamines in high yields. This efficient method allows the diverse synthesis of TPA (tris(2-pyridylmethyl)amine) and TQA (tris(2-quinolylmethyl)amine) derivatives. Among the TQA compounds prepared, tris(8-methoxy-2-quinolylmethyl)amine (8-MeOTQA, 4) exhibited superior properties as a fluorescent zinc probe with high quantum yield (Zn = 0.51) and high sensitivity (limit of detection (LOD) = 3.4 nM). The X-ray crystallographic analysis of [Zn(8-MeOTQA)]2+ revealed that the steric and electronic effect of 8-methoxy substituents kicks out the solvent and counterion molecules from the metal coordination sphere, resulting in short Zn-Nquinoline coordination distances (2.04-2.07 ?). The pseudo hexacoordinate complex of 6-methoxy derivative, [Zn(6-MeOTQA)(DMF)(ClO4)]+, exhibited longer Zn-Nquinoline distances (2.07-2.19 ?) and much smaller fluorescence intensity (Zn = 0.027). The replacement of one of the three 8-methoxyquinolines with pyridine also afforded much less fluorescent zinc complex (Zn = 0.095) due to the solvent coordination (Zn-Nquinoline = 2.05-2.18 ? for [Zn(8-MeOBQPA)(CH3OH)]2+).
- Mikata, Yuji,Nodomi, Yuki,Ohnishi, Risa,Kizu, Asako,Konno, Hideo
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p. 8021 - 8030
(2015/05/13)
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- TERTIARY AMINES FOR USE IN THE TREATMENT OF CARDIAC DISORDERS
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The present invention relates to tertiary amines of formula (I) for use in therapy, particularly for use in treating cardiovascular disorders. The compounds have been found to regulate phospholamban phosphorylation by interfering with the A-kinase anchor protein 18delta (AKAP185) binding to the PKA substrate phospholamban. The compounds share a tri(alkylaryl/alkylheteroaryl) amine structure.
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Page/Page column 118; 119
(2013/12/03)
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- An efficient and practical method for highly chemoselective hydrogenation of nitrobenzylamines to aminobenzylamine hydrochlorides
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Aqueous hydrochloric acid proved to be a very reliable modulator for adjusting the reactivity of palladium on carbon. Thus an efficient and practical method for the highly chemoselective hydrogenation of N,N- dialkylnitrobenzylamines to amino-N,N-dialkylbenzylamine hydrochlorides was established. The method features convenient performance, easy work-up and high efficiency
- Cheng, Chuanjie,Wang, Xinyan,Xing, Lixin,Liu, Bo,Zhu, Rui,Hu, Yuefei
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p. 1775 - 1780
(2008/02/11)
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