1402606-45-4Relevant academic research and scientific papers
Preparation of 3-benzyloxy-2-pyridinone functional linkers: Tools for the synthesis of 3,2-hydroxypyridinone (HOPO) and HOPO/hydroxamic acid chelators
Gibson, Sarah,Fernando, Rasika,Jacobs, Hollie K.,Gopalan, Aravamudan S.
, p. 9271 - 9281 (2015)
In contrast to 2,3-dihydroxypyridine, the 3-benzyloxy protected derivative, 2, undergoes facile alkylation at ambient temperatures with a variety of functionalized alkyl halides in good yields. This alkylation has been used to prepare a number of linkers that permit the attachment of 3,2-HOPO moieties onto various scaffolds using a wide range of coupling methods. The Mitsunobu reaction of 2 with representative alcohols was found to be of limited value due to competing O-alkylation that led to product mixtures. The phthalimide 3j can be converted in two steps to HOPO isocyanate 6 in excellent yields. Isocyanate 6 can be coupled to amines at room temperature or to alcohols in refluxing dichloroethane to obtain the corresponding urea or carbamate linked ligand systems. The coupling of isocyanate 6 with TREN followed by deprotection gave the tris-HOPO 10, an interesting target as it has both cationic and anionic binding sites. The HOPO hydroxylamine linker 11 was shown to be especially valuable as its coupling with carboxylic acids proceeds with the concomitant generation of an additional hydroxamate ligand moiety in the framework. The utility of this linker was shown by the preparation of two mixed HOPO-hydroxamate chelators, 16 and 19, based on the structure of desferrioxamine, a well-known trihydroxamate siderophore.
A practical route for the preparation of 1,4,7-triazacyclononanyl diacetates with a hydroxypyridinonate pendant arm
Gai, Yongkang,Hu, Zhongping,Rong, Zhao,Ma, Xiang,Xiang, Guangya
, p. 19393 - 19405 (2015/11/27)
The preparation of triazamacrocyclic hydroxypyridinonate (HOPO-TACN) derivatives as potential chelators for metals in biomedical applications was reported. The synthesis is based on a convergent synthetic approach, in which the key intermediate di-tert-butyl-2,2′-(1,4,7-triazonane-1,4-diyl) diacetate was coupled with a hydroxypyridinonate pendant arm. The method is suitable for rapid syntheses of metal chelator HOPO-TACNs of biomedical interest.
Organometallic ruthenium and osmium compounds of pyridin-2- and -4-ones as potential anticancer agents
Henke, Helena,Kandioller, Wolfgang,Keppler, Bernhard K.,Hartinger, Christian G.,Hanif, Muhammad
, p. 1718 - 1727,10 (2020/08/24)
Organometallic RuII compounds are among the most widely studied anticancer agents. Functionalizing metal centers with biomolecule-derived ligands has been shown to be a promising strategy to improve the antiproliferative activity of metal-based chemotherapeutics. Herein, the synthesis of a series of novel 3-hydroxypyridin-2-one-derived ligands and their MII(η6-p-cymene) half-sandwich complexes (M=Ru, Os) is described. The compounds were characterized by 1D- and 2D-NMR spectroscopy, and elemental analysis. Copyright
