855464-03-8Relevant academic research and scientific papers
Development of quinone analogues as dynamin GTPase inhibitors
Macgregor, Kylie A.,Abdel-Hamid, Mohammed K.,Odell, Luke R.,Chau, Ngoc,Whiting, Ainslie,Robinson, Phillip J.,McCluskey, Adam
, p. 191 - 206 (2014/08/18)
Virtual screening of the ChemDiversity and ChemBridge compound databases against dynamin I (dynI) GTPase activity identified 2,5-bis-(benzylamino)-1,4- benzoquinone 1 as a 273 ± 106 μM inhibitor. In silico lead optimization and focused library-led synthesis resulted in the development of four discrete benzoquinone/naphthoquinone based compound libraries comprising 54 compounds in total. Sixteen analogues were more potent than lead 1, with 2,5-bis-(4-hydroxyanilino)-1,4-benzoquinone (45) and 2,5-bis(4-carboxyanilino)- 1,4-benzoquinone (49) the most active with IC50 values of 11.1 ± 3.6 and 10.6 ± 1.6 μM respectively. Molecular modelling suggested a number of hydrogen bonding and hydrophobic interactions were involved in stabilization of 49 within the dynI GTP binding site. Six of the most active inhibitors were evaluated for potential inhibition of clathrin-mediated endocytosis (CME). Quinone 45 was the most effective CME inhibitor with an IC50(CME) of 36 ± 16 μM.
Synthesis and biological evaluation of 2,5-bis(alkylamino)-1,4- benzoquinones
Barbosa, Luiz Claudio Almeida,Pereira, Ulisses Alves,Maltha, Celia Regina Alvares,Teixeira, Robson Ricardo,Valente, Vania Maria Moreira,Ferreira, Jose Roberto Oliveira,Costa-Lotufo, Leticia Veras,Moraes, Manoel Odorico,Pessoa, Claudia
experimental part, p. 5629 - 5643 (2010/12/24)
A series of twelve 2,5-bis(alkylamino)-1,4-benzoquinones were prepared in yields ranging from 9-58% via the reaction between p-benzoquinone and various amines. The structures of the synthesized compounds were confirmed by IR, 1H- and 13/s
