1520-97-4Relevant academic research and scientific papers
Structure-activity studies on therapeutic potential of thymoquinone analogs in pancreatic cancer
Banerjee, Sanjeev,Azmi, Asfar S.,Padhye, Subhash,Singh, Marjit W.,Baruah, Jubaraj B.,Philip, Philip A.,Sarkar, Fazlul H.,Mohammad, Ramzi M.
, p. 1146 - 1158 (2010)
Purpose: Pancreatic cancer (PC) is one of the deadliest of all tumors. Previously, we were the first to show that Thymoquinone (TQ) derived from black seed (Nigella sativa) oil has anti-tumor activity against PC. However, the concentration of TQ required
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
2-(N-Alkyl-p-hydroxyanilino)-1,4-benzoquinones from p-Benzoquinones and Primary Aliphatic Amines. Studies on Quinones VI
Ott, Robert,Pinter, Erfried,Kajtna, Peter
, p. 813 - 820 (2007/10/02)
In acetic (aqueous or chloroform) solution p-benzoquinones yield with primary aliphatic amines mainly 2-(N-alkyl-p-hydroxy-anilino)-1,4-benzoquinones besides the 2-alkylamino- and 2,5-bis(alkylamino)-quinones.The methyl-, ethyl-, n-propyl-, n-butylhomologues of p-benzoquinone and the isomer methylderivatives of toluquinone are described.Their structure were established by spectroscopic (UV/VIS, IR, NMR) methods and by synthesis of the methylderivative 3a from p-benzoquinone and p-hydroxy-N-methyl-aniline.The influence of other acids on the reaction was studied. - Keywords: N-Alkyl-p-hydroxyanilino-1,4-quinones; Quinones; Solvent influence
