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Volumn , Issue 4, 2012, Pages 772-779

A multicomponent carba-Betti strategy to alkylidene heterodimers-total synthesis and structure-activity relationships of arzanol

Author keywords

Betti reaction; Drug discovery; Medicinal chemistry; Multicomponent reactions; Natural products; Polyphenols; Synthetic methods

Indexed keywords


EID: 84856140123     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201101193     Document Type: Article
Times cited : (28)

References (27)
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    • Acyphloroglucinols are the single largest class of nonnitrogenous biological MCR adducts
    • Acyphloroglucinols are the single largest class of nonnitrogenous biological MCR adducts. (I. P. Singh, J. Sidana, B. S. Bharatam, W. J. Foley, Nat. Prod. Rep. 2010, 27, 393-416).
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    • Tadeus Reichstein spent the last part of his very long scientific career studying this type of compound
    • Tadeus Reichstein spent the last part of his very long scientific career studying this type of compound (B. Rutkowski, J. Ostrowski, J. Nephrol. 2009, 22, S80-S85).
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    • Remarkably, the eighth of his ten publications on this topic appeared in 1996 when he was 99 years old and the last two appeared posthumously
    • Remarkably, the eighth of his ten publications on this topic appeared in 1996 when he was 99 years old (C.-J. Widen, C. Fraser-Jenkins, T. Reichstein, M. Gibby, S. Jaakko, Ann. Bot. Fenn. 1996, 33, 69-100), and the last two appeared posthumously.
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    • The fame of the Betti base seems to have overshadowed the reaction used for its preparation, which was last reviewed in 1964 and is now considered a special case of the Mannich reaction, which is actually more recent
    • The fame of the Betti base seems to have overshadowed the reaction used for its preparation, which was last reviewed in 1964 (J. P. Phillips, J. L. Travis, Trans. Kent. Acad. Sci. 1964, 23, 95-100), and is now considered a special case of the Mannich reaction, which is actually more recent
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    • The symmetrically substituted trimeric acylphloroglucynol myrtucommulone was recently synthesized using a two-step procedure based on the alkylation of an acylphloroglucynol by a preformed alkylidene dicarbonyl
    • The symmetrically substituted trimeric acylphloroglucynol myrtucommulone was recently synthesized using a two-step procedure based on the alkylation of an acylphloroglucynol by a preformed alkylidene dicarbonyl (H. Muller, M. Paul, D. Hartmann, V. Huch, D. Blaesius, A. Koeberle, O. Werz, J. Jauch, Angew. Chem. 2010, 122, 2089;
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    • G. Appendino, M. Ottino, M. Marquez, F. Bianchi, M. Ballero, O. Sterner, B. L. Fiebich, E. Muñoz J. Nat. Prod 2007, 70, 608-612. Arzanol also shows potent antioxidant activity in several in vitro and biological systems
    • G. Appendino, M. Ottino, M. Marquez, F. Bianchi, M. Ballero, O. Sterner, B. L. Fiebich, E. Muñoz J. Nat. Prod 2007, 70, 608-612. Arzanol also shows potent antioxidant activity in several in vitro and biological systems (, A. Rosa, F. Pollastro, A. Atzeri, G. Appendino, M. P. Melis, M. Deiana, A. Incani, D. Loru, M. A. Dessì, Chem. Phys. Lipids 2011, 164, 24-32.
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    • From 1930-1950, the Tuscan physician Leonardo Santini treated hundreds of patients suffering from inflammatory diseases with preparations from H. italicum. Unfortunately, his studies were published in journals of limited readership and were forgotten after his death. For a summary of Santini's clinical work with this plant, see
    • From 1930-1950, the Tuscan physician Leonardo Santini treated hundreds of patients suffering from inflammatory diseases with preparations from H. italicum. Unfortunately, his studies were published in journals of limited readership and were forgotten after his death. For a summary of Santini's clinical work with this plant, see:, L. Santini, Minerva Med. 1952, 43, 714-719.
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    • Analogues in which the acetyl group is replaced by an isobutyryl or an isovaleryl group and the prenylogues of arzanol can be isolated from H. italicum and/or related species
    • Analogues in which the acetyl group is replaced by an isobutyryl or an isovaleryl group and the prenylogues of arzanol can be isolated from H. italicum and/or related species (R. Haensel, E. M. Cybulski, B. Cubucku, A. H. Mericli, F. Bohlmann, Phytochemistry 1980, 19, 639-644).
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    • 2 by mPGES-1 was analyzed in the microsomal preparation of interleukin-1β-stimulated A549 lung epithelial carcinoma cells. See
    • 2 by mPGES-1 was analyzed in the microsomal preparation of interleukin-1β-stimulated A549 lung epithelial carcinoma cells. See:, A. Koeberle, U. Siemoneit, U. Bühring, H. Northoff, S. Laufer, W. Albrecht, O. Werz, J. Pharmacol. Exp. Ther. 2008, 326, 975-982.
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    • Koeberle, A.1    Siemoneit, U.2    Bühring, U.3    Northoff, H.4    Laufer, S.5    Albrecht, W.6    Werz, O.7
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    • The activity of 5-LO was assessed by measuring the 5-LO products formed in human neutrophils activated by ionophore A23187 and arachidonic acid. See
    • The activity of 5-LO was assessed by measuring the 5-LO products formed in human neutrophils activated by ionophore A23187 and arachidonic acid. See:, O. Werz, E. Buerkert, B. Samuelsson, O. Radmark, D. Steinhilber, Blood 2002, 99, 1044-1052.
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    • Werz, O.1    Buerkert, E.2    Samuelsson, B.3    Radmark, O.4    Steinhilber, D.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.