Synthesis and potent cytotoxic activity of 8- and 9-anilinophenanthridine-7,10-diones

Bernardo, Paul H.; Khanijou, Jasmeet Kaur; Lam, Tze Hau; Tong, Joo Chuan; Chai, Christina L. L.

doi:10.1016/j.tetlet.2010.10.170

Cited by 5 publications

(2 citation statements)

References 16 publications

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“…The molecular frameworks of diverse naturally-occurring cytotoxic compounds, such as smenospongine [1], streptonigrin [2], and mansouramicyn C [3], contain the aminoquinoid moiety as their key structural component (Figure 1). In the field of synthetic cytotoxic aminoquinones, those derived from 1,4-naphthoquinone [4,5,6,7,8] and their heterocyclic analogues [9,10,11,12,13,14,15,16,17] have received considerable attention. However, the synthesis and cytotoxic evaluation of aminobenzoquinones has hitherto received little attention and was mainly focused on the 2,5- bis (arylamino)-1,4-benzoquinone derivatives as compounds A and B .…”

Section: Introductionmentioning

confidence: 99%

Half-Wave Potentials and In Vitro Cytotoxic Evaluation of 3-Acylated 2,5-Bis(phenylamino)-1,4-benzoquinones on Cancer Cells

et al. 2019

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A broad range of 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47–74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against human cancer cells (bladder and prostate) and non-tumor human embryonic kidney cells were measured using the MTT colorimetric method. The substitution of both aniline groups, by either methoxy (electron donating effect) or fluorine (electron withdrawal effect), decreased the cytotoxicity in the aminoquinones. Among the members of the unsubstituted phenylamino series, two of the 18 compounds showed interesting anti-cancer activities. A preliminary assay, looking for changes in the expression of selected genes, was performed. In this context, the two compounds increased TNF gene expression, suggesting an association with an inflammatory-like response.

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Section: Introductionmentioning

confidence: 99%

Half-Wave Potentials and In Vitro Cytotoxic Evaluation of 3-Acylated 2,5-Bis(phenylamino)-1,4-benzoquinones on Cancer Cells

et al. 2019

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“…A number of synthetic aminoisoquinolinequinones and polycyclic analogs have been the subject of study for many years due to their in vitro cytotoxic activities on several cancer cell lines [33,34,35,36,37,38,39]. A well-established procedure to prepare alkyl- and arylaminoquinones is based on the oxidative coupling reaction of quinones with alkyl- and arylamines [40,41,42,43,44]. It is widely accepted that the oxidative coupling reaction involves a Michael addition of the nitrogen nucleophiles to the quinones, followed by oxidation of the hydroquinone intermediates [44].…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis and Electrochemical Properties of Mono- and Dimers Derived from Phenylaminoisoquinolinequinones

et al. 2019

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In the search for new quinoid compounds endowed with potential anticancer activity, the synthesis of novel heterodimers containing the cytotoxic 7-phenylaminoisoquinolinequinone and 2-phenylaminonaphthoquinone pharmacophores, connected through methylene and ethylene spacers, is reported. The heterodimers were prepared from their respective isoquinoline and naphthoquinones and 4,4′-diaminodiphenyl alkenes. The access to the target heterodimers and their corresponding monomers was performed both through oxidative amination reactions assisted by ultrasound and CeCl3·7H2O catalysis “in water”. This eco-friendly procedure was successfully extended to the one-pot synthesis of homodimers derived from the 7-phenylaminoisoquinolinequinone pharmacophore. The electrochemical properties of the monomers and dimers were determined by cyclic and square wave voltammetry. The number of electrons transferred during the oxidation process, associated to the redox potential EI1/2, was determined by controlled potential coulometry.

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Applications of the Sonogashira reaction in the total synthesis of alkaloids

Heravi

Zadsirjan

2021

Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids

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Synthesis and potent cytotoxic activity of 8- and 9-anilinophenanthridine-7,10-diones

Cited by 5 publications

References 16 publications

Half-Wave Potentials and In Vitro Cytotoxic Evaluation of 3-Acylated 2,5-Bis(phenylamino)-1,4-benzoquinones on Cancer Cells

Half-Wave Potentials and In Vitro Cytotoxic Evaluation of 3-Acylated 2,5-Bis(phenylamino)-1,4-benzoquinones on Cancer Cells

Green Synthesis and Electrochemical Properties of Mono- and Dimers Derived from Phenylaminoisoquinolinequinones

Applications of the Sonogashira reaction in the total synthesis of alkaloids

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