Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity

Sun, Qiu; Schmidt, Sebastian; Tremmel, Martina; Heilmann, Jörg; König, Burkhard

doi:10.1016/j.ejmech.2014.08.017

Cited by 12 publications

(11 citation statements)

References 36 publications

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“… 9 , 10 The use of sodium hydroxide led to higher yields of 11 , 12 , 16 , and 17 than the use of lithium hydroxide. Compounds 11 , 8 , 11 − 14 16 , 14 − 17 17 , 18 , 19 and 18 ( 17 , 20 ) have previously been synthesized, and their structures were confirmed by MS and by comparison of their 1 H and 13 C NMR spectra with previously published spectra. Thus, treatment of 10 with 3,3-dimethylallyl bromide (prenyl bromide) in 80% aqueous ethanol with 1.1 equiv of NaOH at room temperature for 16 h gave the monoprenylated product 11 in 33% yield.…”

Section: Resultsmentioning

confidence: 88%

Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

et al. 2016

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The phloroglucinol mallotojaponin C (1) from Mallotus oppositifolius, which was previously shown by us to have both antiplasmodial and cytocidal activities against the malaria parasite Plasmodium falciparum, was synthesized in three steps from 2′,4′,6′-trihydroxyacetophenone, and various derivatives were synthesized in an attempt to improve the bioactivity of this class of compounds. Two derivatives, the simple prenylated phloroglucinols 12 and 13, were found to have comparable antiplasmodial activities to that of mallotojaponin C.

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Section: Resultsmentioning

confidence: 88%

Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

et al. 2016

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“…Nobody would synthesize phloracetophenone by this enzymatic pathway. The simple synthetic solution is the Friedel-Crafts acylation of phloroglucinol, as depicted in Scheme 59 [33,34]. However, via this enzymatic intramolecular aldol condensation processes a variety of aromatic polyketide compounds is available.…”

Section: 2-difunctional Compoundsmentioning

confidence: 99%

Logic of organic chemistry

2016

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A system of logic disconnection or construction of organic molecules is given to overcome serious problems in the study of organic chemistry. Based on the logic system of polar reactions of donors and acceptors several different reactions can be created to access a required target molecule. By a following careful analysis of these proposals several transformations can be detected as the preferred ones. Moreover, by the introduction of the ''umpolung'' principle additional options are given to synthesize a required molecule. These considerations were discussed in the 1,2-, 1,3-, 1,4-, 1,5-and 1,6-difunctional series.

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“…Two series of natural-like acylphloroglucinols were synthesized ( Fig. 6 ) for the systematic investigation of their anti-angiogenic properties [ 59 ].…”

Section: Reviewmentioning

confidence: 99%

“…The compounds of the first series [ 59 ] were prepared starting from 1,3,5-trihydroxybenzene ( 29 , Scheme 7 ). Compounds 30–34 were obtained through Friedel–Crafts acylation of 29 with corresponding acyl chlorides in 55–81% yield.…”

Section: Reviewmentioning

confidence: 99%

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Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

Sun¹,

Heilmann²,

König³

2015

Beilstein J. Org. Chem.

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SummaryConsidering the many secondary natural metabolites available from plants, phenolic compounds play a particularly important role in human health as they occur in significant amounts in many fruits, vegetables and medicinal plants. In this review natural phenolic compounds of plant origin with significant anti-angiogenic properties are discussed. Thirteen representatives from eight different natural or natural-like phenolic subclasses are presented with an emphasis on their synthesis and methods to modify the parent compounds. When available, the consequence of structural variation on the pharmacological activity of the molecules is described.

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Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity

Cited by 12 publications

References 36 publications

Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

Logic of organic chemistry

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

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