3421-08-7Relevant academic research and scientific papers
Synthesis, electrochemical and anti-microbial study of 2,5-diamino benzoquinones
Asha,Suma
, (2021/12/29)
Fifteen symmetric and unsymmetric 2,5-diamino benzoquinones have been synthesized and their electrochemical activity was studied by cyclic voltammetry. Presence of electron donating substituent like amino group found to shift the half wave potential towar
Benzoquinone Derivatives For Treatment Of Cancer And Methods Of Making The Benzoquinone Derivatives
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Paragraph 0123; 0137, (2017/10/23)
The present invention benzoquinone derivatives of the formula (I): and to pharmaceutically acceptable salts or solvates thereof. In formula (I) one of X or Y is hydrogen and the other one of X or Y is 3-Trifluoro-methylaniline; 3,4,5-trifluoroaniline; 4-methoxylaniline; 4-fluoroaniline; 3,3′-Dimethyl-1,1′-Biphenyl-4,4′-diamine; 2-(pyrrolidin-l-yl)ethyl)amine; 4-trifluoromethyl-benzylamine ; 4-fluorobenzyl-amine; 3,4-dimethoxybenzylamine; or 3,5-ditrifluoromethyl-benzylamine. Compounds of formula (I) have been identified as being useful in the treatment of cancer, in particular lung, breast and pancreatic cancer. The invention relates also to a method of making the benzoquinone derivatives and to methods of treatment.
Electronic effects of ligand substitution on spin crossover in a series of diiminoquinonoid-bridged feii2 complexes
Park, Jesse G.,Jeon, Ie-Rang,Harris, T. David
, p. 359 - 369 (2015/05/26)
A series of four isostructural FeII2 complexes, [(TPyA)2Fe2(XL)]2+ (TPyA = tris(2-pyridylmethyl)amine; XL2- = doubly deprotonated form of 3,6-disubstituted-2,5-dianili
Electronic effects of ligand substitution on spin crossover in a series of diiminoquinonoid-bridged FeII2 complexes
Park, Jesse G.,Jeon, Ie-Rang,Harris, T. David
, p. 359 - 369 (2017/01/17)
A series of four isostructural FeII2 complexes, [(TPyA)2Fe2(XL)]2+ (TPyA = tris(2-pyridylmethyl)amine; XL2-= doubly deprotonated form of 3,6-disubstituted-2,5-dianilin
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 of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase
Berhe, Solomon,Slupe, Andrew,Luster, Choice,Charlier Jr., Henry A.,Warner, Don L.,Zalkow, Leon H.,Burgess, Edward M.,Enwerem, Nkechi M.,Bakare, Oladapo
experimental part, p. 134 - 141 (2010/04/06)
A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 μM. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with KI values ranging between 2 and 11 μM. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme.
Structure-reactivity correlation of anilines in acid medium
Karunakaran,Kandasamy,Palanisamy
, p. 2630 - 2634 (2007/10/03)
The chromium(VI) oxidation of aniline in aqueous acetic acid is first order with respect to chromium(VI), aniline and H+ of the medium. Analysis of the structure-reactivity relationship using the method followed hitherto shows poor correlation. But correlation of the reaction rates of molecular anilines with the oxidizing species yields satisfactory results.
Reactions of Biogenic Amines with Quinones
Tindale, C.Ross
, p. 611 - 617 (2007/10/02)
Reactions of benzo-1,4-quinone with 2-phenylethylamine and p-tyramine produced the novel 2,5-diamino-derivatives (2b,c), analogous to 2,5-dianilinobenzo-1,4-quinone (2a). 2,5-Dihydroxybenzo-1,4-quinone (3) reacts with aniline to form the tetrol (4a) and not 2,5-dianilinobenzo-1,4-quinone (2a) as previously reported.This tetrol (4a) may hydrolyse to form the monoimine (5a).Only in boiling aniline was the 2,5-dianilino derivative (2a) produced from the tetrol (4a).Novel tetrols were similarly isolated from 2-phenylethylamine, p-tyramine and histamine.Benzo-1,2-quinone reactions with aniline and the above amines were also studied.Implications of these reactions for the extraction of amines from food are discussed.
Aryl Nitrenes from N,N'-Diarylbenzoquinone Di-imine N,N'-Dioxides and N-Arylbenzoquinone Imine N-Oxides
Forrester, Alexander R.,Ogilvy, Munro M.,Thomson, Ronald H.
, p. 2023 - 2026 (2007/10/02)
Photolyses of the title quinone imine N.oxides give mainly azoarenes formed by dimerisation of triplet aryl nitrenes.
