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SYNTHESIS OF BENZYLIDENEACETOPHENONE …

20/02/2006 · Synthesis and evaluation of biological properties of benzylideneacetophenone ..

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Yakuchinone B is a constituent of seeds from A. oxyphylla, a member of the ginger family (Zingiberaceae) commonly used in folk medicine. It shows a variety of biological effects including anti-inflammatory activity, as demonstrated by its strong inhibitory effect on prostaglandin biosynthesis in vitro. Like curcumin, yakuchinone B has a diarylheptanoid moiety with a carbonyl functional group that is known to possess strong anti-oxidative and anti-inflammatory activities. One author of the current study (S. Oh) previously designed and synthesized novel benzylideneacetophenone derivatives (JC1 to JC5) on the basis of the structure of yakuchinone B, and showed that they exert a protective effect on brain ischemia both in vitro and in vivo. In the present investigation, all compounds synthesized in this series (JC1 to JC5) showed considerable suppression of IFN-γ-induced IP-10/CXCL10 expression in orbital fibroblasts (data not shown). JC3, however, showed the greatest inhibitory effect, suppressing IFN-γ-induced IP-10/CXCL10 expression to a greater extent than yakuchinone B (). The greater efficacy of JC3 is likely related to its structural characteristics; it is inherently stable due to electron delocalization, and likely engages in hydrogen bonding with its receptor-binding site (the benzylideneacetophenone derivative) to exert its potent inhibitory effect. Polystructures of JC3 compounds (JC3 dimer and JC3 trimer) also suppressed IFN-γ-induced IP-10/CXCL10 expression in orbital fibroblasts with greater potency than JC3 monomers, suggesting that the structure of JC3 is critical for suppression of IFN-γ-induced IP-10/CXCL10 expression.

The synthesis of benzylideneacetophenone derivatives was initiated as described previously
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The synthesis of benzylideneacetophenone derivatives was initiated as described previously.24 The 4-hydroxy-3-methoxy cinnamaldehyde was protected with tert-butyldimethylsilyl trifluoromethanesulfonate in the presence of 2,6-lutidine or 2-(trimethylsilyl) ethoxymethyl chloride (SEM–Cl)/N,N-di-isopropylethylamine to form aldehydes with 95 and 97% yields, respectively. Benzylideneacetophenone compound (JC3) was fully identified by infrared and NMR spectroscopy, including high-resolution mass spectroscopy. In addition, dimers (JC3-D) and trimers (JC3-T) of JC3 were constructed to evaluate the efficacy of polystructures of JC3 ().

Chalcone is an enone on which a variety of structures are based

20/12/2017 · JC1 to JC5 are benzylideneacetophenone derivatives that were synthesized based on a structural modification of yakuchinone B …
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Yakuchinone B, a constituent of the seeds of Alpinia oxyphylla, which belongs to the ginger family (Zingiberaceae), has been commonly used in folk medicine. According to several studies, yakuchinone B is known to have significant biological effects such as anti-inflammatory, antitumor and antiviral activities. JC1 to JC5 are benzylideneacetophenone derivatives that were synthesized based on a structural modification of yakuchinone B in previous efforts to develop neuroprotective agents. These derivatives showed beneficial effects in neurodegenerative diseases, suggesting the efficacy of these compounds as therapeutic agents for particular diseases.

(Benzylideneacetophenone) -----11.

Benzylideneacetophenone is the parent member of the chalcone series
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The alternative name given to chalcone are phenyl styryl ketone, ..
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  • Chalcones are also intermediates in the Auwers synthesis of flavones.

    Chalcone - Wikipedia

  • The method according to synthesis of the chalcone series

    Graves' Ophthalmopathy — NEJM

  • Benzylideneacetophenone is the parent member

    Chalcone - LKT Labs

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