332402-91-2Relevant academic research and scientific papers
A microwave-assisted nucleophilic substitution reaction on a quinoline system: The synthesis of amino analogues of nitroxoline
?tefane, Bogdan,Po?gan, Franc,Sosi?, Izidor,Gobec, Stanislav
, p. 1964 - 1967 (2012)
A reliable protocol for the synthesis of a series of 8-amino analogues of pharmacologically interesting nitroxoline (5-nitro-8-hydroxyquinoline) is described. The unprecedented displacement of the cyanomethoxy group of an O-cyanomethylated quinoline deriv
Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO3)3·9H2O as Promoter and Nitro Source
He, Yan,Zhao, Ningning,Qiu, Liqi,Zhang, Xinying,Fan, Xuesen
supporting information, p. 6054 - 6057 (2016/12/09)
An efficient and regioselective remote C(5)-H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO3)3·9H2O as promoter and nitro source has been developed. Furthermore, when CuCl2·2H2O was used as a catalyst, 8-aminoquinoline amides dominantly underwent bisnitration to give 5,7-dinitro-8-aminoquinoline amides. Notably, this is the first example in which Fe(NO3)3·9H2O plays a dual role as both chelating promoter and nitration reagent, and CuCl2·2H2O acts as an efficient catalyst for the bisnitration of quinolines.
Development of new cathepsin b inhibitors: Combining bioisosteric replacements and structure-based design to explore the structure-activity relationships of nitroxoline derivatives
Sosi?, Izidor,Mirkovi?, Bojana,Arenz, Katharina,?tefane, Bogdan,Kos, Janko,Gobec, Stanislav
, p. 521 - 533 (2013/04/24)
Human cathepsin B has many house-keeping functions, such as protein turnover in lysosomes. However, dysregulation of its activity is associated with numerous diseases, including cancers. We present here the structure-based design and synthesis of new cathepsin B inhibitors using the cocrystal structure of 5-nitro-8-hydroxyquinoline in the cathepsin B active site. A focused library of over 50 compounds was prepared by modifying positions 5, 7, and 8 of the parent compound nitroxoline. The kinetic parameters and modes of inhibition were characterized, and the selectivities of the most promising inhibitors were determined. The best performing inhibitor 17 was effective in cell-based in vitro models of tumor invasion, where it significantly abrogated invasion of MCF-10A neoT cells. These data show that we have successfully explored the structure-activity relationships of nitroxoline derivatives to provide new inhibitors that could eventually lead to compounds with clinical usefulness against the deleterious effects of cathepsin B in cancer progression.
