101565-87-1Relevant articles and documents
Novel iron complexes bearing N6-substituted adenosine derivatives: Synthesis, magnetic, 57Fe Moessbauer, DFT, and in vitro cytotoxicity studies
Travnicek, Zdenek,Mikulik, Jiri,Cajan, Michal,Zboril, Radek,Popa, Igor
experimental part, p. 8719 - 8728 (2009/04/11)
Iron complexes (1-7) involving N6-benzyladenosine derivatives of the predominant composition [Fe(Ln)Cl3] · H2O {where L1 = N6-(2-fluorobenzyl)adenosine (1), L2 = N6-(4-fluorobenzyl)adenosine (2), L3 = N6-(2-trifluoromethylbenzyl)adenosine (3), L4 = N6-(3-trifluoromethylbenzyl)adenosine (4), L5 = N6-(4-trifluoromethylbenzyl)adenosine (5), L6 = N6-(4-trifluoromethoxybenzyl)adenosine (6), and L7 = N6-(4-chlorobenzyl)adenosine (7)} have been synthesized. The compounds have been characterized by elemental analysis, variable-temperature and in-field 57Fe Moessbauer, ES+ MS, FTIR, 1H and 13C NMR spectroscopies, magnetochemical and conductivity measurements, thermal (TGA/DSC/DTA) analyses, and DFT calculations. It has been found that the organic molecule is coordinated to iron via N7 atom of the appropriate adenosine derivative and the products are represented by mixtures of complexes with various iron oxidation (FeIII/FeII) and spin states (S = 5/2, 4/2, 3/2, 2/2) and geometries (tetrahedral or trigonal bipyramidal). It is caused by the fact that partial redox processes proceed during the reactions due to the presence of a ribose moiety, which is oxidized to the corresponding 5′-ribotic acid, and simultaneously, a portion of FeIII cations is reduced to FeII ones. Moreover, a significant effect of crystal water molecules on stereochemistry, and hence, on magnetic and spectral properties of the prepared complexes has been found. The compounds have been tested for their in vitro cytotoxicity against the following human cancer cell lines: malignant melanoma (G-361), osteogenic sarcoma (HOS), chronic myelogenous leukemia (K-562), and breast adenocarcinoma (MCF-7). The most important results have been obtained for complex 2 with IC50 values 8-16 μM against HOS, K-562, and MCF-7 cell lines, and for complex 6 with IC50 value 4 μM against MCF-7 cell line.
Preparation, biological activity and endogenous occurrence of N6-benzyladenosines
Dolezal, Karel,Popa, Igor,Hauserova, Eva,Spichal, Lukas,Chakrabarty, Kuheli,Novak, Ondrej,Krystof, Vladimir,Voller, Jiri,Holub, Jan,Strnad, Miroslav
, p. 3737 - 3747 (2008/02/07)
Cytokinin activity of forty-eight 6-benzyladenosine derivatives at both the receptor and cellular levels as well as their anticancer properties were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine rib
Dog Coronary Artery Adenosine Receptor: Structure of N6-Aryl Subregion
Kusachi,Shozo,Thompson, Robert D.,Yamada, Nobuyuki,Daly, Daniel T.,Olsson, R. A.
, p. 989 - 996 (2007/10/02)
Previous structure-coronary vasoactivity correlations of the N6-alkyladenosine analogues of N6-adenosine, 1, support the hypothesis that the coronary artery A2 adenosine receptor contains an N6 region of specialized structure.The part of this receptor region that binds the 2-propyl moiety of 1 determines stereoselectivity and contributes to coronary vasoactivity.The present study uses 92 adenosine analogues containing an aryl group in the N6 substituent to test the hypothesis that the N6 receptor region contains and aryl subregionthat binds the phenyl moiety of 1 and thereby contributes to its coronary vasoactivity.N6-Aralkyladenosines are often more potent than their alkyl congeners.Two methylene residues seem to provide optimum separation of the aryl group from N6.Among adenosines with semirigid N6 substituents, N6-adenosine was uniquely active, evidence that when 1 occupies the receptor, the axis of the propyl C-1 to phenyl C-1 bond is nearly in the plane described by N6 and propyl C-1 and C-2.The torsion angle around this bond is unknown.Replacing the phenyl group of N6-2-phenethyladenosine with a thienyl or a 3-pyridyl group raises activity.The structure-activity relationships of the N6-(arylethyl)-, the N6-(arylmethyl)-, and the N6-phenyladenosines differ strinkingly from each other.Taken together, such results support the idea that the N6 region of the dog coronary artery A2 adenosine receptor includes an aryl subregion.
