5440-48-2Relevant articles and documents
Synthesis of Functionalised Phenylalanines Using Rhodium Catalysis in Water
Chapman, Christopher J.,Frost, Christopher G.
, p. 353 - 355 (2007/10/03)
The efficient synthesis of substituted phenylalanine-type amino acids using a rhodium-catalysed, conjugate addition of arylboronic acids is described. The reactions are run in water and use a low loading (0.5 mol %) of rhodium catalyst.
TRICYCLIC AMIDES
-
, (2008/06/13)
The invention relates to a compound selected from these of formula (I) : STR1 in which R 7, R 8, Y, n and A are as defined in the description, and medicinal product containing the same useful for treating a disorder of the melatoninergic system.
Synthesis of 2-amido-2,3-dihydro-1H-phenalene derivatives as new conformationally restricted ligands for melatonin receptors
Mathé-Allainmat, Monique,Gaudy, Florence,Sicsic, Sames,Dangy-Caye, Anne-Laure,Shen, Shuren,Brémont, Béatrice,Benatalah, Zohra,Langlois, Michel,Renard, Pierre,Delagrange, Philippe
, p. 3089 - 3095 (2007/10/03)
Tetrahydroanthracene, tetrahydrophenanthrene, and tetrahydrophenalene moieties were used to design novel constrained melatoninergic agents. Compounds 1 and 2 were synthesized from the cyclization of the aryl succinic acids 6a,b followed by catalytic reduction, Curtius degradation to the amino derivatives, and acetylation. The phenalene derivatives 3 were prepared by cyclization of the aza lactones of the corresponding α-N-acetyl amino acids. The ketone derivatives were reduced directly by catalytic hydrogenation to produce the compounds 3. The different compounds were evaluated in vitro in binding assays using 2-[125I]iodomelatonin and chicken brain membranes. Melatonin and 2-acetamido-8-methoxytetralin were used as the reference compounds. The results showed the superiority of the dihydrophenalene framework 3 over those of tetrahydroanthracene and tetrahydrophenanthrene. 3a had relatively good affinity for melatonin receptors (K(i) = 28.7 nM). Introduction of an additional methoxy group gave a derivative (3c) with nanomolar affinity (K(i) = 0.7 nM), confirming the existence of a secondary binding site in the receptor which has been described previously. An increase in the affinity was also observed with the propionamido derivative 3e (K(i) = 6.0 nM). The potential agonist properties of the compound 3e were evaluated on the dermal melanocytes of Xenopus laevis tadpoles. At the concentration of 2.3 nM (5 x K(i)), melatonin gave a melanophore index value of 1. Similarly to melatonin, 3e was shown to be a potent agonist of the melanosome aggregation.
