126278-83-9Relevant academic research and scientific papers
Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases
Lucchesini, Francesco,Pocci, Marco,Alfei, Silvana,Bertini, Vincenzo,Buffoni, Franca
supporting information, p. 1558 - 1567 (2014/03/21)
In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs. With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic ω-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B. The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects.
Manganese-catalyzed substitution of activated aryl halides (X = Cl, Br and F) and aryl ethers by organomagnesium reagents
Cahiez, Gerard,Lepifre, Franck,Ramiandrasoa, Parfait
, p. 2138 - 2144 (2007/10/03)
In the presence of manganese chloride (10%), Grignard reagents readily react in THF with aryl bromides, chlorides and even fluorides, as well as aryl methyl ethers bearing in the ortho- or para-position an electron withdrawing activating group (CN, CH=NR, oxazoline). Aryl and N- or S- alkylmagnesium halides have been used successfully. The reaction is performed under mild conditions (0 °C to room temperature, 30 minutes to 24 hours) and leads to cross-coupling products in good yields.
Nucleophilic aromatic substitution on aromatic aldimines
Flippin, Lee A.,Carter, David S.,Dubree, Nathan J. P.
, p. 3255 - 3258 (2007/10/02)
Ortho-methoxy-substituted benzaldimines derived from 3-amino-2,4-dimethylpentane undergo efficient nucleophilic aromatic substitution with typical organolithium reagents. The aldimine products can be hydrolyzed under mild conditions to provide ortho-alkyl or ortho-phenyl benzaldehyde derivatives.
PALLADIUM-MEDIATED 2,6-DIALKYLATION OF N-BENZILIDINE IMINES: PREPARATION OF 2,6-DIALKYLBENZALDEHYDES
McCallum, J. Stuart,Gasdaska, John R.,Liebeskind, Lanny S.
, p. 4085 - 4088 (2007/10/02)
Treatment of di-μ-trifluoroacetatobisdipalladium with two equivalents of primary alkyl iodides and subsequent hydrolysis provides an efficient route to 2,6-disubstituted benzaldehydes.
