Anti-tumoral activities of dioncoquinones B and C and related naphthoquinones gained from total synthesis or isolation from plants

Bringmann, Gerhard; Zhang, Guoliang; Hager, Anastasia; Moos, Michael; Irmer, Andreas; Bargou, Ralf C.; Chatterjee, Manik

doi:10.1016/j.ejmech.2011.09.012

Cited by 39 publications

(23 citation statements)

References 55 publications

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“…To find the best reaction conditions for the synthesis of the prototype menadione derivatives, 6‐methoxy‐2‐methylnaphthol ( 4a ) was chosen as the model substrate to optimize the reaction conditions. In the literature, many oxidizing agents have been employed for this purpose, including copper or copper(II) chloride (CuCl 2 ),22a hypervalent iodine derivatives (phenyliodonium diacetate, PIDA),30 Fremy's salt,31 manganese dioxide (MnO 2 ),32 chromium trioxide (CrO 3 ),33 and radical oxidation [cerium(IV) ammonium nitrate, CAN],34 to cite but a few. We tested several conditions for the oxidation of 6‐methoxy‐2‐methylnaphthol to 6‐methoxymenadione (Table 1).…”

Section: Resultsmentioning

confidence: 99%

A Platform of Regioselective Methodologies to Access Polysubstituted 2‐Methyl‐1,4‐naphthoquinone Derivatives: Scope and Limitations

Rodo¹,

Feng²,

Jida³

et al. 2016

Eur J Org Chem

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A platform of synthetic methodologies has been established to access a focused library of polysubstituted 3‐benzylmenadione derivatives functionalized on the aromatic ring of the naphthoquinone core. Two main routes were explored: 1) The naphthol route, starting from either an α‐tetralone or a propiophenone, and 2) the regioselective Diels–Alder reaction, starting from various dienes and two 2‐bromo‐5(or 6)‐methyl‐1,4‐benzoquinones. 6‐Substituted 2‐methylnaphthols were synthesized by using a xanthate‐mediated free‐radical addition/cyclization sequence for the construction of the 6‐substituted menadione subunit. Furthermore, an efficient and simple new pathway that allows the formation of 6‐ or 7‐substituted 3‐(substituted‐benzyl)menadione regioisomers from a common commercial scaffold has also been developed by the naphthol route, advantageous with regard to step economy. Our synthetic methodologies exemplified by 34 compounds have allowed structure–activity relationships to be deduced for use as the basis for the development of new antimalarial redox‐active polysubstituted benzylmenadione derivatives.

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Section: Resultsmentioning

confidence: 99%

A Platform of Regioselective Methodologies to Access Polysubstituted 2‐Methyl‐1,4‐naphthoquinone Derivatives: Scope and Limitations

Rodo¹,

Feng²,

Jida³

et al. 2016

Eur J Org Chem

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“…83) A new series of 1,4-naphthoquinones, bearing various cyclic and aliphatic amines at 2-position, were designed and synthesized to identify antiproliferative agents for triple-negative breast cancer. Among them two compounds (64)(65) (Fig. 16) significantly inhibited in vitro the proliferation of MDA-MB-231 cells.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 97%

“…11), showed a significant activity against the parasitic protists of Leishmania major. In subsequent studies, the biologically active nucleus of natural quinones was modified by organic synthesis 63,64) and the newly obtained biologically active derivatives of these 1,4-naphthoquinones were patented. 65) The efficacy of a series of 2-hydroxy-3-phenylsulfanylmethyl- [ (46) (Fig.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 99%

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1,4-Naphthoquinones: Some Biological Properties and Application

2020

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Over the past decade, a number of new 1,4-naphthoquinones have been isolated from natural sources and new 1,4-naphthoquinones with diverse structural features have been synthesized. Cardioprotective, antiischemic, hepatoprotective, neuroprotective and some other new properties were found for these compounds; their role in protecting against neurodegenerative diseases has been established. Their anti-inflammatory, antimicrobial and antitumor activities have been studied in more detail; new, previously unknown intracellular molecular targets and mechanisms of action have been discovered. Some compounds of this class are already being used as a medicinal drugs and some substances can be used as biochemical tools and probes for non-invasive detection of pathological areas in cells and tissues in myocardial infarction and neurodegenerative diseases using modern molecular imaging techniques.

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“…Plumbagin (10) and 7-methyljuglone (11) occur in species-specific ratios, for example, in Drosera [78,82]. In A. heyneanus, large amounts of plumbagin (10) accumulate around the haustoria of a haloparasite, killing it [85,88,93]. Naphthylisoquinoline alkaloids, such as dioncophylline A (12), are produced by T. peltatum, the formation of which from its two polyketide-derived molecular halves is stress-sensitive.…”

Section: The Main Naphthoquinone-containing Orders Caryophyllalesmentioning

confidence: 99%