19133-61-0Relevant academic research and scientific papers
Synthesis of quinone imine and sulphur-containing compounds with antitumor and trypanocidal activities: Redox and biological implications
Almeida, Renata G.,Barbosa, Juliana M. C.,De Carvalho, Guilherme G. C.,De Castro, Solange L.,De Simone, Carlos A.,Goulart, Marilia O. F.,Kharma, Ammar,Paier, Carlos R. K.,Pessoa, Claudia,Pinheiro, Daniel P.,Da Silva Júnior, Eufranio N.,Rosa, Luísa G.,Valen?a, Wagner O.
, p. 1145 - 1160 (2020/11/03)
Ortho-Quinones represent a special class of redox active compounds associated with a spectrum of pronounced biological activities, including selective cytotoxicity and antimicrobial actions. The modification of the quinone ring by simple nitrogen and sulphur substitutions leads to several new classes of compounds with their own, distinct redox behaviour and equally distinct activities against cancer cell lines and Trypanosoma cruzi. Some of the compounds investigated show activity against T. cruzi at concentrations of 24.3 and 65.6 μM with a selectivity index of around 1. These results demonstrate that simple chemical modifications on the ortho-quinone ring system, in particular, by heteroatoms such as nitrogen and sulphur, transform these simple redox molecules into powerful cytotoxic agents with considerable "potential", not only in synthesis and electrochemistry, but also, in a broader sense, in health sciences. This journal is
O-Iodoxybenzoic Acid-Initiated One-Pot Synthesis of 4-Arylthio-1,2-naphthoquinones, 4-Arylthio-1,2-diacetoxynaphthalenes, and 5-Arylthio-/5-Aminobenzo[a]phenazines
Mishra, Abhaya Kumar,Moorthy, Jarugu Narasimha
, p. 6472 - 6480 (2016/08/16)
1,2-Naphthoquiones and their derivatives constitute an important category of compounds of relevance in pharmaceutical and material chemistry. It is shown that 1,2-naphthoquinones generated by o-iodoxybenzoic acid-mediated oxidation of 2-naphthols can be subjected to a cascade of reactions, namely oxidation, Michael addition, reduction, acetylation, and cyclocondensation, in the same pot to afford diverse 4-arylthio-1,2-naphthoquinones 2, 4-arylthio-1,2-diacetoxynaphthalenes 3, and 5-arylthio-/5-aminobenzo[a]phenazines 4 in very good isolated yields. The multistep single-pot synthesis occurs smoothly in DMF at rt.
Quinones. Part 11. The Reaction of o-Aminothiophenol with o-Benzo- and o-Naphtho-quinones: A New Route to 1H-Phenothiazin-1-ones
Mackenzie, Neil E.,Surendrakumar, Sivagnanasundram,Thomson, Ronald H.,Cowe, Heather J.,Cox, Philip J.
, p. 2233 - 2242 (2007/10/02)
1H-Phenothiazin-1-ones can be obtained by the condensation of o-aminothiophenol with 3,5-di-t-butyl- and 3-t-butyl-5-phenyl-o-benzoquinones.In the absence of large blocking groups the phenothiazinones are unstable.A methyl group at C-4 leads via the quinone-methide tautomer, to formation of a spiro-dimer the crystal structure of which was determined by X-ray analysis.By further reaction with o-aminothiophenol, 1H-phenothiazin-1-ones yield triphenodithiazines (benzothiazinophenothiazines). o-Naphthoquinones do not form benzo-1H-phenothiazin-1-ones with o-aminothiophenol.The parent compound yields 4-hydroxy-3H-benzophenothiazin-3-one by initial thiol addition at C-4 followed by rearrangement.
