84953-64-0Relevant articles and documents
Pure enantiomers of benzoylamino-tranylcypromine: LSD1 inhibition, gene modulation in human leukemia cells and effects on clonogenic potential of murine promyelocytic blasts
Valente, Sergio,Rodriguez, Veronica,Mercurio, Ciro,Vianello, Paola,Saponara, Bruna,Cirilli, Roberto,Ciossani, Giuseppe,Labella, Donatella,Marrocco, Biagina,Monaldi, Daria,Ruoppolo, Giovanni,Tilset, Mats,Botrugno, Oronza A.,Dessanti, Paola,Minucci, Saverio,Mattevi, Andrea,Varasi, Mario,Mai, Antonello
, p. 163 - 174 (2015/03/18)
The pure enantiomers of the N-(2-, 3-, and 4-(2-aminocyclopropyl)phenyl)benzamides hydrochlorides 11a-j were prepared and tested against LSD1 and MAO enzymes. The evaluation of the regioisomers 11a-j highlighted a net increase of the anti-LSD1 potency by
Exploring distal regions of the A3 adenosine receptor binding site: Sterically constrained N6-(2-phenylethyl)adenosine derivatives as potent ligands
Tchilibon, Susanna,Kim, Soo-Kyung,Gao, Zhan-Guo,Harris, Brian A.,Blaustein, Joshua B.,Gross, Ariel S.,Duong, Heng T.,Melman, Neli,Jacobson, Kenneth A.
, p. 2021 - 2034 (2007/10/03)
We synthesized phenyl ring-substituted analogues of N6-(1S,2R)- (2-phenyl-1-cyclopropyl)adenosine, which is highly potent in binding to the human A3AR with a Ki value of 0.63nM. The effects of these structural changes on affinity at human and rat adenosine receptors and on intrinsic efficacy at the hA3AR were measured. A 3-nitrophenyl analogue was resolved chromatographically into pure diastereomers, which displayed 10-fold stereoselectivity in A3AR binding in favor of the 1S,2R isomer. A molecular model defined a hydrophobic region (Phe168) in the putative A3AR binding site around the phenyl moiety. A heteroaromatic group (3-thienyl) could substitute for the phenyl moiety with retention of high affinity of A3AR binding. Other related N6-substituted adenosine derivatives were included for comparison. Although the N 6-(2-phenyl-1-cyclopropyl) derivatives were full A3AR agonists, several other derivatives had greatly reduced efficacy. N 6-Cyclopropyladenosine was an A3AR antagonist, and adding either one or two phenyl rings at the 2-position of the cyclopropyl moiety restored efficacy. N6-(2,2-Diphenylethyl)adenosine was an A 3AR antagonist, and either adding a bond between the two phenyl rings (N6-9-fluorenylmethyl) or shortening the ethyl moiety (N 6-diphenylmethyl) restored efficacy. A QSAR study of the N 6 region provided a model that was complementary to the putative A3AR binding site in a rhodopsin-based homology model. Thus, a new series of high-affinity A3AR agonists and related nucleoside antagonists was explored through both empirical and theoretical approaches.
The structure and conformation of 1-phenyl-2-methylcyclopropene-3-carboxylic acid and cis-2-(m-nitrophenyl)cyclopropanecarboxylic acid
Korp, James D.,Bernal, Ivan,Fuchs,, Richard
, p. 50 - 56 (2007/10/02)
The structures of cis-2-(m-nitrophenyl)cyclopropanecarboxylic acid (1) and 1-phenyl-2-methylcyclopropene-3-carboxylic acid (2) have been determined by X-ray methods.Crystal of 1 are triclinic, space group P1, with a=9.499 Angstroem, α=60.24, β=63.76, γ=71.36, and two molecules in the unit cell.Crystals of are monoclinic, space group P21/c, with four molecules in a unit cell of dimensions a=9.354, b=13.286, c=8.187 Angstroem, and β=98.22.The carboxyl group of 1 approaches the bisecting conformation.The phenyl group is 37 deg from this conformation, by contrast with the unhindered compound 2-(p-nitrophenyl)cyclopropyl methyl ketone.In 2 the carboxyl group bisect the three-membered ring, indicating that carbonyl-cyclopropene ? interactions can oocur if sterically allowed.The two rings are essentially coplanar, permitting maximum interaction of the phenyl group and the double bond.In both compounds, the carbonyl oxygen of the carboxyl is the nearer oxygen to the three-membered ring.
