The radical reactions of imine radicals produced from the metal salts oxidation of 2-amino-1,4-benzoquinones

Lu, Po Yuan; Chen, Kuang Po; Chuang, Che Ping

doi:10.1016/j.tet.2009.07.025

Cited by 5 publications

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“…Twistane (tricyclo[4.4.0.0 , ]decane), the twist-boat isomer of adamantane, and its simple functionalized derivatives were first synthesized in 1962 . In sharp contrast to adamantane analogues which have received huge attention, these cage-shaped systems have been the subject of limited studies.…”

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confidence: 99%

“…Despite these features, only a limited number of syntheses en route to this skeleton are available. These are generally based on intramolecular enolate alkylations of prefunctionalized bicyclo[2.2.2]octan-2-one or cis- bicicyclo[4.4.0]decanediones . More direct strategies based on a two-bond disconnection through an intramolecular Diels–Alder cycloaddition (IMDA) have proven to favor the formation of a less strained 5/6/6 isotwistane (tricyclo[4.3.1.0 , ]decane) framework (Scheme ) …”

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Synthesis of Indole Substituted Twistenediones from a 2-Quinonyl Boronic Acid

et al. 2013

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Indole substituted twistane-like derivatives resulted in a reaction between 3,5-dimethyl-2-quinonyl boronic acid and 2-alkenyl indoles. Their MCPBA oxidation gave 6/6/9 caged systems. Boronic acid acts as a temporal promoter allowing a site-selective conjugate addition of the heteroaromatic system to the methyl substituted C-3 quinone carbon, giving an intermediate diene which is regioselectively trapped by intramolecular [4 + 2] cycloaddition.

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Synthesis of Indole Substituted Twistenediones from a 2-Quinonyl Boronic Acid

et al. 2013

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Ammonium Peroxydisulfate

Behrman¹,

Neufeldt²

2012

Encyclopedia of Reagents for Organic Synthesis

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Discovery and structure–activity relationship of plastoquinone analogs as anticancer agents against chronic myelogenous leukemia cells

Çiftçi

Bayrak

Yıldırım

et al. 2019

Archiv der Pharmazie

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Two series of amino‐1,4‐benzoquinones (AQ1–18) based on the structural analogs of plastoquinones were synthesized and the structure–activity relationship against chronic myelogenous leukemia activity was examined. All of the synthesized compounds were tested for their cytotoxic effects on different leukemic cell lines. Of interest, AQ15 exhibited a better selectivity than the reference drug imatinib on cancer cells. Owing to this, AQ15 was selected for a further apoptosis/necrosis evaluation where AQ15‐treated K562 cells demonstrated similar apoptotic effects like imatinib‐treated cells at their IC50 values. The inhibitory effects of AQ15 and the other three compounds with various activities against eight tyrosine kinases, including ABL1, were investigated. AQ15 showed weak activity against ABL1, and a correlation was observed between the anti‐K562 and anti‐ABL1 activities. The binding mode of AQ15 into the ATP binding pocket of ABL1 kinase was predicted in silico, showing the formation of some key interactions. In addition, AQ15 was shown to suppress the downstream signaling of BCR‐ABL in K562 cells. Finally, AQ15 obviously cleaved DNA in the presence of an iron(II) complex system, indicating that this can be the major mechanism of its antiproliferative action, whereas the mild inhibition of ABL kinase is just in‐part mechanism of its overall outstanding cellular activity.

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The radical reactions of imine radicals produced from the metal salts oxidation of 2-amino-1,4-benzoquinones

Cited by 5 publications

References 47 publications

Synthesis of Indole Substituted Twistenediones from a 2-Quinonyl Boronic Acid

Synthesis of Indole Substituted Twistenediones from a 2-Quinonyl Boronic Acid

Ammonium Peroxydisulfate

Discovery and structure–activity relationship of plastoquinone analogs as anticancer agents against chronic myelogenous leukemia cells

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