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Volumn 37, Issue 5, 2007, Pages 675-681

First total synthesis of cytotoxic diarylheptanoids, galeon, and pterocarine

Author keywords

Aldol; Cytotoxicity; Diatrylheptanoid; Galeon; Pterocarine; Ullmann reaction

Indexed keywords

ALDEHYDE DERIVATIVE; BIPHENYL DERIVATIVE; CYTOTOXIC AGENT; ETHER; GALEON; KETONE DERIVATIVE; NATURAL PRODUCT; PTEROCARINE; UNCLASSIFIED DRUG;

EID: 33847146291     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601131015     Document Type: Article
Times cited : (12)

References (38)
  • 1
    • 77957022760 scopus 로고    scopus 로고
    • Keserü, G. M.; Nógrádi, M. The chemistry of natural diarylheptanoids. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: New York, 1995, 17; pp. 357-394.
    • Keserü, G. M.; Nógrádi, M. The chemistry of natural diarylheptanoids. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: New York, 1995, 17; pp. 357-394.
  • 2
    • 33845557330 scopus 로고
    • Reaction of aryl and vinyl halides with zerovalent nickel-preparative aspects and the synthesis of alnusone
    • and references therein
    • Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Mendelson, L.; Ryono, L. S.; Smith, J. G.; Stauffer, R. D. Reaction of aryl and vinyl halides with zerovalent nickel-preparative aspects and the synthesis of alnusone. J. Am. Chem. Soc. 1981, 103, 6460-6471, and references therein.
    • (1981) J. Am. Chem. Soc , vol.103 , pp. 6460-6471
    • Semmelhack, M.F.1    Helquist, P.2    Jones, L.D.3    Keller, L.4    Mendelson, L.5    Ryono, L.S.6    Smith, J.G.7    Stauffer, R.D.8
  • 3
    • 0017871633 scopus 로고
    • Cyclisation of 1,7-diarylheptanoids through oxidative, reductive, and photochemical radical processes: Total syntheses of the m,m-bridged biaryls myricanone and (±)-myricanol, and a related diaryl ether
    • Whiting, D. A.; Wood, A. F. Cyclisation of 1,7-diarylheptanoids through oxidative, reductive, and photochemical radical processes: Total syntheses of the m,m-bridged biaryls myricanone and (±)-myricanol, and a related diaryl ether. Tetrahedron Lett. 1978, 2335-2338.
    • (1978) Tetrahedron Lett , pp. 2335-2338
    • Whiting, D.A.1    Wood, A.F.2
  • 4
    • 37049108166 scopus 로고
    • Total syntheses of the meta, meta-bridged biphenyls (±)-myricanol and myricanone, and of an isomeric biphenyl ether, a 14-oxa[7,1]meta-paracyclophane
    • Whiting, D. A.; Wood, A. F. Total syntheses of the meta, meta-bridged biphenyls (±)-myricanol and myricanone, and of an isomeric biphenyl ether, a 14-oxa[7,1]meta-paracyclophane. J. Chem. Soc., Perkin Trans. 1 1980, 623-628.
    • (1980) J. Chem. Soc., Perkin Trans. 1 , pp. 623-628
    • Whiting, D.A.1    Wood, A.F.2
  • 6
    • 0026029402 scopus 로고
    • Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis
    • Huang, M.-T.; Lysz, T.; Ferraro, T.; Abidi, T. F.; Laskin, J. D.; Conney, A. H. Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis. Cancer Res. 1991, 51, 813-819.
    • (1991) Cancer Res , vol.51 , pp. 813-819
    • Huang, M.-T.1    Lysz, T.2    Ferraro, T.3    Abidi, T.F.4    Laskin, J.D.5    Conney, A.H.6
  • 7
    • 25844469952 scopus 로고    scopus 로고
    • Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs
    • Lee, S.-L.; Huang, W.-J.; Lin, W. W.; Lee, S.-S.; Chen, C.-H. Preparation and anti-inflammatory activities of diarylheptanoid and diarylheptylamine analogs. Bioorg. Med. Chem. 2005, 13, 6175-6181.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 6175-6181
    • Lee, S.-L.1    Huang, W.-J.2    Lin, W.W.3    Lee, S.-S.4    Chen, C.-H.5
  • 8
    • 33847135590 scopus 로고    scopus 로고
    • Weber, W. M.; Hunsaker, L. A.; Deck, L. M.; Vander Jagt, D. L. Synthesis of enone analogues of the natural product curcumin. Abstracts of Papers, 230th ACS National Meeting, American Chemical Society, Washington, DC, United States, Aug. 28-Sept. 1, 2005, MEDI-149.
    • Weber, W. M.; Hunsaker, L. A.; Deck, L. M.; Vander Jagt, D. L. Synthesis of enone analogues of the natural product curcumin. Abstracts of Papers, 230th ACS National Meeting, American Chemical Society, Washington, DC, United States, Aug. 28-Sept. 1, 2005, MEDI-149.
  • 9
    • 15044362170 scopus 로고    scopus 로고
    • Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents
    • Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2005, 15, 1793-1797.
    • (2005) Bioorg. Med. Chem. Lett , vol.15 , pp. 1793-1797
    • Selvam, C.1    Jachak, S.M.2    Thilagavathi, R.3    Chakraborti, A.K.4
  • 10
    • 0041548059 scopus 로고
    • Antibacterial action of curcumin and related compounds
    • Schraufstatter, E.; Bernt, H. Antibacterial action of curcumin and related compounds. Nature (London) 1949, 164, 456-457.
    • (1949) Nature (London) , vol.164 , pp. 456-457
    • Schraufstatter, E.1    Bernt, H.2
  • 11
    • 0032732191 scopus 로고    scopus 로고
    • H-atom transfer is a preferred antioxidant mechanism of curcumin
    • Jovanovic, S. V.; Steenken, S.; Boone, C. W.; Simic, G. H-atom transfer is a preferred antioxidant mechanism of curcumin. J. Am. Chem. Soc. 1999, 121, 9677-9681.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 9677-9681
    • Jovanovic, S.V.1    Steenken, S.2    Boone, C.W.3    Simic, G.4
  • 12
    • 0034618287 scopus 로고    scopus 로고
    • On the antioxidant mechanism of curcumin: Classical methods are needed to determine antioxidant mechanism and activity
    • Barclay, L. R. C.; Vinqvist, M. R.; Kazuo Mukai, K.; Goto, H.; Hashimoto, Y.; Tokunaga, A.; Uno, H. On the antioxidant mechanism of curcumin: Classical methods are needed to determine antioxidant mechanism and activity. Org. Lett. 2000, 2, 2841-2843.
    • (2000) Org. Lett , vol.2 , pp. 2841-2843
    • Barclay, L.R.C.1    Vinqvist, M.R.2    Kazuo Mukai, K.3    Goto, H.4    Hashimoto, Y.5    Tokunaga, A.6    Uno, H.7
  • 13
    • 0023790908 scopus 로고
    • Inhibitory effect of curcumin, chlorogenic acid, caffeic acid and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate
    • For curcumins
    • For curcumins: Huang, M.-T.; Smart, R. C.; Wong, C.-Q.; Conney, A. H. Inhibitory effect of curcumin, chlorogenic acid, caffeic acid and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res. 1988, 48, 5941-5946.
    • (1988) Cancer Res , vol.48 , pp. 5941-5946
    • Huang, M.-T.1    Smart, R.C.2    Wong, C.-Q.3    Conney, A.H.4
  • 14
    • 0027173480 scopus 로고
    • Inhibitory effects of curcumin on protein kinase C activity induced by 12-O-tetradecanoylphorbol-13-acetate in NIH 3T3 cells
    • Liu, J.-Y.; Lin, S.-J.; Lin, J.-K. Inhibitory effects of curcumin on protein kinase C activity induced by 12-O-tetradecanoylphorbol-13-acetate in NIH 3T3 cells. Carcinogenesis 1993, 14, 857-861.
    • (1993) Carcinogenesis , vol.14 , pp. 857-861
    • Liu, J.-Y.1    Lin, S.-J.2    Lin, J.-K.3
  • 16
    • 0034739711 scopus 로고    scopus 로고
    • Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis
    • For biphenylheptaoids
    • For biphenylheptaoids: Ishida, J.; Kozuka, M.; Wang, H.-K.; Konoshima, T.; Tokuda, H.; Okuda, M.; Yang Mou, X.; Nishino, H.; Sakurai, N.; Lee, K.-H.; Nagai, M. Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. Cancer Lett. 2000, 159, 135-140.
    • (2000) Cancer Lett , vol.159 , pp. 135-140
    • Ishida, J.1    Kozuka, M.2    Wang, H.-K.3    Konoshima, T.4    Tokuda, H.5    Okuda, M.6    Yang Mou, X.7    Nishino, H.8    Sakurai, N.9    Lee, K.-H.10    Nagai, M.11
  • 18
    • 0037250029 scopus 로고    scopus 로고
    • Structure of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense
    • Morikawa, T.; Tao, J.; Toguchida, I.; Matsuda, H.; Yoshikawa, M. Structure of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense. J. Nat. Prod. 2003, 66, 86-91.
    • (2003) J. Nat. Prod , vol.66 , pp. 86-91
    • Morikawa, T.1    Tao, J.2    Toguchida, I.3    Matsuda, H.4    Yoshikawa, M.5
  • 20
    • 37049103197 scopus 로고    scopus 로고
    • Nagai, M.; Kubo, M.; Fujita, M.; Inoue, T.; Matsuo, M. Acerogenin A, a novel cyclic diarylheptanoid. Chem. Commun. 1976, 338-339.
    • Nagai, M.; Kubo, M.; Fujita, M.; Inoue, T.; Matsuo, M. Acerogenin A, a novel cyclic diarylheptanoid. Chem. Commun. 1976, 338-339.
  • 21
    • 0018175622 scopus 로고    scopus 로고
    • Nagai, M.; Kubo, M.; Fujita, M.; Inoue, T.; Matsuo, M. Studies on the constituents of Aceroceae plants, II: Structure of aceroside I, a glucoside of a novel cyclic diarylheptanoid from Acer nikoense Maxim. Chem. Pharm. Bull. 1978, 26, 2805-2810.
    • Nagai, M.; Kubo, M.; Fujita, M.; Inoue, T.; Matsuo, M. Studies on the constituents of Aceroceae plants, II: Structure of aceroside I, a glucoside of a novel cyclic diarylheptanoid from Acer nikoense Maxim. Chem. Pharm. Bull. 1978, 26, 2805-2810.
  • 22
    • 85011210228 scopus 로고
    • Studies on the constituents of aceroceae plants, III: Structure of acerogenin B from Acer nikoense Maxim
    • Kubo, M.; Inoue, T.; Nagai, M. Studies on the constituents of aceroceae plants, III: Structure of acerogenin B from Acer nikoense Maxim. Chem. Pharm. Bull. 1980, 28, 1300-1303.
    • (1980) Chem. Pharm. Bull , vol.28 , pp. 1300-1303
    • Kubo, M.1    Inoue, T.2    Nagai, M.3
  • 23
    • 84998354953 scopus 로고    scopus 로고
    • Kubo, M.; Nagai, M.; Inoue, T. Studies on the constituents of Aceroceae plants, IV: Carbon-13 nuclear magnetic resonance spectra of acerogenin A, rhododendrol, and related compounds, and structure of aceroside IV from Acer nikoense. Chem. Pharm. Bull. 1983, 31, 1917-1922.
    • Kubo, M.; Nagai, M.; Inoue, T. Studies on the constituents of Aceroceae plants, IV: Carbon-13 nuclear magnetic resonance spectra of acerogenin A, rhododendrol, and related compounds, and structure of aceroside IV from Acer nikoense. Chem. Pharm. Bull. 1983, 31, 1917-1922.
  • 24
    • 84998389435 scopus 로고
    • Studies on the constituents of Aceraceae plants, V: Two diarylheptanoid glycosides and an arylbutanol apiosylglucoside from Acer nikoense
    • Nagai, M.; Kubo, M.; Takahashi, K.; Fujita, M.; Inoue, T. Studies on the constituents of Aceraceae plants, V: Two diarylheptanoid glycosides and an arylbutanol apiosylglucoside from Acer nikoense. Chem. Pharm. Bull. 1983, 31, 1923-1928.
    • (1983) Chem. Pharm. Bull , vol.31 , pp. 1923-1928
    • Nagai, M.1    Kubo, M.2    Takahashi, K.3    Fujita, M.4    Inoue, T.5
  • 25
    • 85008076999 scopus 로고    scopus 로고
    • Nagai, M.; Kenmochi, N.; Fujita, M.; Furukawa, N.; Inoue, T. Studies on the constituents of Aceraceae plants, VI: Revised stereochemistry of (-)-centrolobol, and new glycosides from Acer nikoense. Chem. Pharm. Bull. 1986, 34, 1056-1060.
    • Nagai, M.; Kenmochi, N.; Fujita, M.; Furukawa, N.; Inoue, T. Studies on the constituents of Aceraceae plants, VI: Revised stereochemistry of (-)-centrolobol, and new glycosides from Acer nikoense. Chem. Pharm. Bull. 1986, 34, 1056-1060.
  • 26
    • 0027183831 scopus 로고    scopus 로고
    • Nagumo, S.; Kaji, N.; Inoue, T.; Nagai, M. Studies on the constituents of Aceraceae plants, XI: Two types of cyclic diarylheptanoid from Acer nikoense. Chem. Pharm. Bull. 1993, 41, 1255-1257.
    • Nagumo, S.; Kaji, N.; Inoue, T.; Nagai, M. Studies on the constituents of Aceraceae plants, XI: Two types of cyclic diarylheptanoid from Acer nikoense. Chem. Pharm. Bull. 1993, 41, 1255-1257.
  • 27
    • 0000572732 scopus 로고
    • 14-Oxa-[7.1] metaparacyclophanes from Myrica gale L., a new class of natural products
    • Malterud, K. E.; Anthonsen, T.; Hjortas, J. 14-Oxa-[7.1] metaparacyclophanes from Myrica gale L., a new class of natural products. Tetrahedron Lett. 1976, 35, 3069-3070.
    • (1976) Tetrahedron Lett , vol.35 , pp. 3069-3070
    • Malterud, K.E.1    Anthonsen, T.2    Hjortas, J.3
  • 28
    • 0030957708 scopus 로고    scopus 로고
    • Two novel diarylheptanoid glucosides from Myrica gale var. tomentosa and absolute structure of plane-chiral galeon
    • Morihara, M.; Sakurai, N.; Inoue, T.; Kawai, K.-I.; Nagai, M. Two novel diarylheptanoid glucosides from Myrica gale var. tomentosa and absolute structure of plane-chiral galeon. Chem. Pharm. Bull. 1997, 45, 820-823.
    • (1997) Chem. Pharm. Bull , vol.45 , pp. 820-823
    • Morihara, M.1    Sakurai, N.2    Inoue, T.3    Kawai, K.-I.4    Nagai, M.5
  • 29
    • 33745056505 scopus 로고    scopus 로고
    • 1 phase and induction of apoptosis in HCT-15 and K562 cells. Chin. Chem. Lett. 2005, 16, 215-218.
    • 1 phase and induction of apoptosis in HCT-15 and K562 cells. Chin. Chem. Lett. 2005, 16, 215-218.
  • 30
    • 0030773677 scopus 로고    scopus 로고
    • First total synthesis of acerogenin C and aceroside IV
    • Isalas Gonzalez, G.; Zhu, J. First total synthesis of acerogenin C and aceroside IV. J. Org. Chem. 1997, 62, 7544-7545.
    • (1997) J. Org. Chem , vol.62 , pp. 7544-7545
    • Isalas Gonzalez, G.1    Zhu, J.2
  • 31
    • 0344076297 scopus 로고    scopus 로고
    • A unified strategy toward the synthesis of acerogenin-type macrocycles: Total syntheses of acerogenin A, B, C, and L and aceroside IV
    • Isalas Gonzalez, G.; Zhu, J. A unified strategy toward the synthesis of acerogenin-type macrocycles: Total syntheses of acerogenin A, B, C, and L and aceroside IV. J. Org. Chem. 1999, 64, 914-924.
    • (1999) J. Org. Chem , vol.64 , pp. 914-924
    • Isalas Gonzalez, G.1    Zhu, J.2
  • 32
    • 0344935513 scopus 로고    scopus 로고
    • Synthesis of acerogenin C and (+)-acerogenin A, two macrocyclic diarylheptanoids constituents of Acer nikoense
    • Keserü, G. M.; Nógródi, M.; Szöllösy, A. Synthesis of acerogenin C and (+)-acerogenin A, two macrocyclic diarylheptanoids constituents of Acer nikoense. Eur. J. Org. Chem. 1998, 521-524.
    • (1998) Eur. J. Org. Chem , pp. 521-524
    • Keserü, G.M.1    Nógródi, M.2    Szöllösy, A.3
  • 34
    • 37049135506 scopus 로고
    • Bush pungent compounds, part I: An improved synthesis of the paradols (alkyl 4-hydroxy-3-methoxyphenethyl ketones) and an assessment of their pungency
    • Locksley, H. D.; Rainey, D. K.; Rohan, T. A. Bush pungent compounds, part I: An improved synthesis of the paradols (alkyl 4-hydroxy-3-methoxyphenethyl ketones) and an assessment of their pungency. J. Chem. Soc., Perkin Trans. 1 1972, 3001-3006.
    • (1972) J. Chem. Soc., Perkin Trans. 1 , pp. 3001-3006
    • Locksley, H.D.1    Rainey, D.K.2    Rohan, T.A.3
  • 35
    • 0020589463 scopus 로고
    • Synthesis of diarylheptanoids and assessment of their pungency
    • Itokawa, H.; Aiyama, R.; Ikuta, A. Synthesis of diarylheptanoids and assessment of their pungency. Chem. Pharm. Bull. 1983, 31, 2491-2496.
    • (1983) Chem. Pharm. Bull , vol.31 , pp. 2491-2496
    • Itokawa, H.1    Aiyama, R.2    Ikuta, A.3
  • 36
    • 0342757538 scopus 로고    scopus 로고
    • Recent advances in diaryl ether synthesis
    • For a review based on the reaction mechanism, see
    • For a review based on the reaction mechanism, see Sawyer, J. S. Recent advances in diaryl ether synthesis. Tetrahedron 2000, 56, 5045-5065.
    • (2000) Tetrahedron , vol.56 , pp. 5045-5065
    • Sawyer, J.S.1
  • 37
    • 0345329013 scopus 로고
    • Copper assisted nucleophilic substitution of aryl halogen
    • For a review for the classical Ullmann reaction condition, see
    • For a review for the classical Ullmann reaction condition, see Lindley, J. Copper assisted nucleophilic substitution of aryl halogen. Tetrahedron 1984, 40, 1433-1456.
    • (1984) Tetrahedron , vol.40 , pp. 1433-1456
    • Lindley, J.1
  • 38
    • 0024508264 scopus 로고
    • The total syntheses of the isodityrosine-derived cyclic tripeptides OF4949-I11 and K-13: Determination of the absolute configuration of K-13
    • Evans, D. A.; Ellman, J. A. The total syntheses of the isodityrosine-derived cyclic tripeptides OF4949-I11 and K-13: Determination of the absolute configuration of K-13. J. Am. Chem. Soc. 1989, 111, 1063-1072.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 1063-1072
    • Evans, D.A.1    Ellman, J.A.2


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