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Synthesis and characterization of novel unnatural bichalcones

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Abstract

Five bichalcones (5-15-4, 9) were prepared by the reaction of biphenyl-4,4′-dicarbaldehyde (4) and 4,4′-dioxybenzaldehyde (8) with the respective acetophenone analogs via Claisen-Schmidt condensation and were then fully identified by 1H-NMR, 13C-NMR and mass analyses.

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References

  • Amellal, M., Bronner, C., Briancon, F., Hagg, M., Anton, R., and Landry, Y., Inhibition of mast cell histamine release by flavonoids and biflavonoids. Planta Med., 51, 16–20 (1985).

    Article  CAS  PubMed  Google Scholar 

  • Chen, J., Chang, H. W., Kim, H. P., and Park, H., Synthesis of phospholipase A2 inhibitory biflavonoids. Bioorg. Med. Chem. Lett., 16, 2373–2375 (2006).

    Article  CAS  PubMed  Google Scholar 

  • Dao, T. T., Chi, Y. S., Kim, J., Kim, H. P., Kim, S., and Park, H., Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives. Bioorg. Med. Chem. Lett., 14, 1165–1167 (2004).

    Article  CAS  PubMed  Google Scholar 

  • Gawronski, J., Brzostowska, M., Kwit, M., Plutecka, A., and Rychlewska, U., Rhombimines-cyclic tetraimines of trans-1,2-diaminocyclohexane shaped by the diaryl ether structural motif. J. Org. Chem., 70, 10147–10150 (2005).

    Article  CAS  PubMed  Google Scholar 

  • Giroux, A., Han, Y., and Prasit, P., One pot biaryl synthesis via in situ boronate formation. Tetrahedron Lett., 38, 3841–3844 (1997).

    Article  CAS  Google Scholar 

  • Kim, H. K., Son, K. H., Chang, H. W., Kang, S. S., and Kim, H. P., Inhibition of rat adjuvant-induced arthritis by ginkgetin, a biflavone from ginkgo biloba leaves. Planta Med., 65, 465–467 (1999).

    Article  CAS  PubMed  Google Scholar 

  • Kim, Y. H., Kim, J., Park, H., and Kim, H. P., Anti-inflammatory activity of the synthetic chalcone derivatives: inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells. Biol. Pharm. Bull., 30, 1450–1455 (2007).

    Article  CAS  PubMed  Google Scholar 

  • Kuhnert, N., Pate, C., and Jami, F., Synthesis of chiral nonracemic polyimine macrocycles from cyclocondensation reactions of biaryl and terphenyl aromatic dicarboxaldehydes and 1R,2R-diaminocyclohexane. Tetrahedron Lett., 46, 7575–7579 (2005).

    Article  CAS  Google Scholar 

  • Lin, Y. M., Flavin, M. T., Cassidy, C. S., Mar, A., and Chen, F. C., Biflavonoids as novel antituberculosis agents. Bioorg. Med. Chem. Lett., 11, 2101–2104 (2001).

    Article  CAS  PubMed  Google Scholar 

  • Mdee, L. K., Yeboah, S. O., and Abegaz, B. M., Rhuschalcones II–VI, five new bichalcones from the root bark of Rhus pyroides. J. Nat. Prod., 66, 599–604 (2003).

    Article  CAS  PubMed  Google Scholar 

  • Miyaura, N. and Suzuki, A., Palladium-catalyzed crosscoupling reactions of organoboron compounds. Chem. Rev., 95, 2457–2483 (1995).

    Article  CAS  Google Scholar 

  • Moutloali, R. M., Nevondo, F. A., Darkwa, J., Iwuoha, E. I., and Henderson, W., Bimetallic nickel complexes with bridging dithiolato Schiff base ligands: synthesis, mass spectral characterisation and electrochemistry. J. Organomet. Chem., 656, 262–269 (2002).

    Article  CAS  Google Scholar 

  • Murakami, M., Shimbara, S., Kambe, T., Kuwata, H., Winstead, M. V., Tischfield, J. A., and Kudo, I., The functions of five distinct mammalian phospholipase A2s in regulating arachidonic acid release. Type IIa and type V secretory phospholipase A2s functionally redundant and act in concert with cytosolic phospholipase A2. J. Biol. Chem., 273, 14411–14423 (1998).

    Article  CAS  PubMed  Google Scholar 

  • Murakami, M., Kambe, T., Shimbara, S., Higashino, K., Hanasaki, K., Arita, H., Horiguchi, M., Arita, M., Arai, H., Inoue, K., and Kudo, I., Different functional aspects of the group II subfamily (Types IIA and V) and type X secretory phospholipase A2s in regulating arachidonic acid release and prostaglandin generation. Implication of cyclooxygenase-2 induction and phospholipids scramblase-mediated cellular membrane perturbation. J. Biol. Chem., 274, 31435–31444 (1999).

    Article  CAS  PubMed  Google Scholar 

  • Sawada, H., Murakami, M., Enomoto, A., Shimbara, S., and Kudo, I., Regulation of type V phospholipase A2 expression and function by proinflammatory stimuli. Eur. J. Biochem., 263, 826–835 (1999).

    Article  CAS  PubMed  Google Scholar 

  • Sawyer, J. S., Recent advances in diaryl ether synthesis. Tetrahedron, 56, 5045–5065 (2000).

    Article  Google Scholar 

  • Shinohara, H., Balboa, M. A., Johnson, C. A., Balsinde, J., and Dennis, E. A., Regulation of delayed prostaglandin production in activated P338D1 macrophages by group IV cytosolic and group V secretory phospholipase A2s. J. Biol. Chem., 274, 12263–12268 (1999).

    Article  CAS  PubMed  Google Scholar 

  • Stille, J. K., The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles. Angew. Chem. Int. Ed. Engl., 95, 2457 (1995).

    Google Scholar 

  • Sun, C. M., Syu, W. J., Huang, Y. T., Chen, C. C., and Ou, J. C., Selective cytotoxicity of ginkgetin from Selaginella moellendorffii. J. Nat. Prod., 60, 382–384 (1997).

    Article  CAS  PubMed  Google Scholar 

  • Yang, J., Tyberg, C. S., and Gibson, H. W., A Polyketone synthesis involving nucleophilic substitution via carbanions derived from bis(R-aminonitrile)s. 4.1-3 aromatic poly (ether ketone)s. Macromolecules, 32, 8259–8268 (1999).

    Article  CAS  Google Scholar 

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Correspondence to Haeil Park.

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Gurung, S.K., Kim, S.B. & Park, H. Synthesis and characterization of novel unnatural bichalcones. Arch. Pharm. Res. 33, 1919–1926 (2010). https://doi.org/10.1007/s12272-010-1205-2

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  • DOI: https://doi.org/10.1007/s12272-010-1205-2

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