16055-14-4Relevant academic research and scientific papers
Making organoruthenium complexes of 8-hydroxyquinolines more hydrophilic: Impact of a novel l-phenylalanine-derived arene ligand on the biological activity
Movassaghi, Sanam,Hanif, Muhammad,Holtkamp, Hannah U.,S?hnel, Tilo,Jamieson, Stephen M. F.,Hartinger, Christian G.
, p. 2192 - 2201 (2018)
Ru(arene) compounds have many desirable features making them promising candidates for further development in anticancer drug research. While a lot of emphasis has been placed on the modification of the ancillary ligands, there are not many examples of arene ligands bearing functional groups. Herein, we report the preparation of [Ru(arene)(8-oxyquinolinato)Cl] complexes with the arene being a protected form of the amino acid l-phenylalanine and 8-oxyquinolinato ligand substituted with halogens. With this approach we aimed to alter the pharmacological properties of the complexes and address issues with the aqueous solubility of the analogous p-cymene complexes. The complexes were shown to be stable in DMSO and water and reacted readily with l-histidine and 9-ethylguanine as protein and DNA models, respectively. Assaying the antiproliferative activity in cancer cells gave IC50 values in the low μM range. While the lipophilicity of the p-cymene analogues correlated well with their in vitro cytotoxicity, the potency of the complexes with the l-phenylalanine-derived arene was independent of lipophilicity.
Ozonolysis of (cyclohexa-1,4-dienyl)-L-alanine. An approach to the synthesis of new unnatural aminoacids. X-Ray molecular structure of 2-hydroxy-7-methyl-3-phenylpyrazolopyrimidine
Zvilichovsky, Gury,Gurvich, Vadim
, p. 2509 - 2516 (2007/10/02)
The aromatic ring in L-phenylalanine was transformed into isoxazolyl, N-phenylpyrazolyl, and the bicyclic pyrazolopyrimidinyl groups, by a combination of Birch reduction and ozonolysis, followed by condensation with the relevant binucleophiles.The ozonolysis was carried out on the N-acylated esters of cyclohexa-1,4-dienylalanine.The resulting N-acylated esters of heterocyclic alanine derivatives were obtained without isolation of the ozonolysis products. 4-Phenylpyrazolidine-3,5-dione was used as a 'hydrazine donor' in the construction of pyrazolyl group, as direct condensation with hydrazine was successful.
