27828-56-4Relevant academic research and scientific papers
Experimental study of bimolecular reaction kinetics in porous media
Kapoor,Raje
, p. 1234 - 1239 (2000)
A biomolecular reaction (1,2-naphthoquinone-4-sulfonic acid + aniline → 1,2-naphthoquinone-4-aminobenzene) in a saturated porous media flow in a column was studied to experimentally demonstrate the importance of reactant segregation in porous media flow.
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
Discovery of naphtho[1,2-d]oxazole derivatives as potential anti-HCV agents through inducing heme oxygenase-1 expression
Tseng, Chih-Hua,Lin, Chun-Kuang,Chen, Yeh-Long,Tseng, Chin-Kai,Lee, Jar-Yu,Lee, Jin-Ching
, p. 970 - 982 (2017/12/15)
A number of naphtho[1,2-d]oxazole derivatives were synthesized and evaluated for their anti-HCV virus activity. Among them, compound 18 was the most active, exhibited approximately 21-folds more active anti-HCV activity (IC50 of 0.63 μM) than t
Selective Inhibitors of Human Liver Carboxylesterase Based on a β-Lapachone Scaffold: Novel Reagents for Reaction Profiling
Hatfield, M. Jason,Chen, Jingwen,Fratt, Ellie M.,Chi, Liying,Bollinger, John C.,Binder, Randall J.,Bowling, John,Hyatt, Janice L.,Scarborough, Jerrod,Jeffries, Cynthia,Potter, Philip M.
supporting information, p. 1568 - 1579 (2017/03/08)
Carboxylesterases (CEs) are ubiquitous enzymes that are responsible for the metabolism of xenobiotics, including drugs such as irinotecan and oseltamivir. Inhibition of CEs significantly modulates the efficacy of such agents. We report here that β-lapachone is a potent, reversible CE inhibitor with Ki values in the nanomolar range. A series of amino and phenoxy analogues have been synthesized, and although the former are very poor inhibitors, the latter compounds are highly effective in modulating CE activity. Our data demonstrate that tautomerism of the amino derivatives to the imino forms likely accounts for their loss in biological activity. A series of N-methylated amino derivatives, which are unable to undergo such tautomerism, were equal in potency to the phenoxy analogues and demonstrated selectivity for the liver enzyme hCE1. These specific inhibitors, which are active in cell culture models, will be exceptionally useful reagents for reaction profiling of esterified drugs in complex biological samples.
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.
Synthesis and anti-inflammatory evaluations of β-lapachone derivatives
Tseng, Chih-Hua,Cheng, Chih-Mei,Tzeng, Cherng-Chyi,Peng, Shin-I,Yang, Chiao-Li,Chen, Yeh-Long
, p. 523 - 531 (2013/02/25)
β-Lapachone (β-LAPA), a natural product from the lapacho tree in South America, is a potential chemotherapeutic agent that exhibit a wide variety of pharmacological effects such as anti-virus, anti-parasitic, anti-cancer, and anti-inflammatory activities.
Synthesis and optical properties of acidochromic amine-substituted benzo[a]phenazines
Singh, Prachi,Baheti, Abhishek,Thomas, K. R. Justin
supporting information; experimental part, p. 6134 - 6145 (2011/10/09)
A new series of alkylamine- or arylamine-substituted benzo[a]phenazines have been synthesized from 1,2-naphthoquinones by employing simple sequential Michael-type addition with a variety of primary and secondary amines and the condensation reaction of the resulting amine-substituted 1,2-naphthoquinones with o-phenylenediamine. They exhibited absorption peaks originating from the charge transfer transition between the amine and pyrazine segments and benzo[a]phenazine localized π-π* transitions. Although the absorption spectra of the dyes were not significantly influenced by the nature of the solvents, addition of TFA led to a prominent red-shift in the absorption spectra owing to the protonation at the quinoxaline segment which enhanced the electron-accepting ability. The qualitative trends observed in the optical properties and acidochromism were supported by density functional theoretical computations. The dyes displayed positive solvatochromism in the emission spectra suggestive of a more polar excited state. The dyes were also characterized by a quasi-reversible reduction couple originating from the pyrazine segment which underwent shifts corresponding to electron-donating strength of the amine segment.
HEAT SHOCK PROTEIN 90 INHIBITORS, METHODS OF PREPARING SAME, AND METHODS FOR THEIR USE
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Page/Page column 14, (2010/04/28)
Novel classes of molecular chaperone Heat shock protein 90 (Hsp90) inhibitors are disclosed. These compounds are useful in treating and preventing cancer and other Hsp90-related diseases and conditions, such as inflammation and neurodegenerative disorders. Methods of treating and preventing cancer and other Hsp90 related diseases and conditions are disclosed that include administering to the subject a therapeutically effective amount of an Hsp90 inhibitor. Methods of preparing the novel Hsp90 inhibitors are also provided.
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.
CATALYTIC TRANSAMINATION OF DIALKYLAMINO-o-QUINONES
Tsizin, Yu. S.,Chernyak, S. A.,Kornienko, N. I.
, p. 2381 - 2388 (2007/10/02)
The ions of transition and alkaline-earth metals catalyze the transamination of bicyclic dialkylamino-o-quinones by primary and secondary amines.The effectiveness of the catalysis is determined by the type of chelate complex formed by the o-quinones and b
