Synthesis of Highly Functionalized Anthraquinones and Evaluation of Their Antitumor Activity

作者: Lutz F. Tietze , Kersten M. Gericke , Ingrid Schuberth

DOI: 10.1002/EJOC.200700418

关键词: Human lungIn vitro growthSide chainIslandicinAntitumor activityChemistryAnthraquinonesCycloadditionMensacarcinOrganic chemistry

摘要: Highly functionalized anthraquinones which derive from the natural products mensacarcin, islandicin, and chrysophanol have been efficiently synthesized using a Diels–Alder reaction as key step. The introduction of proposed pharmacophoric side chain unit has achieved by an addition aryllithium species onto different aldehydes. Furthermore, antitumor activity these novel compounds studied in vitro growth inhibition human lung carcinoma cells line A549.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

参考文章(73)
A. V. Patudin, A. I. Ban'kovskii, A. S. Romanova, Quinones of higher plants as possible therapeutic agents Pharmaceutical Chemistry Journal. ,vol. 11, pp. 927- 937 ,(1977) , 10.1007/BF00778021
Wilfred Louis Florio Armarego, Douglas Dalzell Perrin, D. R Perrin, Purification of laboratory chemicals ,(1966)
S.O Mueller, M Schmitt, W Dekant, H Stopper, J Schlatter, P Schreier, W.K Lutz, Occurrence of emodin, chrysophanol and physcion in vegetables, herbs and liquors. Genotoxicity and anti-genotoxicity of the anthraquinones and of the whole plants. Food and Chemical Toxicology. ,vol. 37, pp. 481- 491 ,(1999) , 10.1016/S0278-6915(99)00027-7
SK Agarwal, Sudhir S Singh, Sushma Verma, Sushil Kumar, None, Antifungal activity of anthraquinone derivatives from Rheum emodi Journal of Ethnopharmacology. ,vol. 72, pp. 43- 46 ,(2000) , 10.1016/S0378-8741(00)00195-1
Gerhard Bringmann, Dirk Menche, Jürgen Kraus, Jörg Mühlbacher, Karl Peters, Eva-Maria Peters, Reto Brun, Merhatibeb Bezabih, Berhanu M. Abegaz, Atropo-enantioselective total synthesis of knipholone and related antiplasmodial phenylanthraquinones. Journal of Organic Chemistry. ,vol. 67, pp. 5595- 5610 ,(2002) , 10.1021/JO020189S
Bruce Armitage, Changjun Yu, Chelladurai Devadoss, Gary B. Schuster, Cationic Anthraquinone Derivatives as Catalytic DNA Photonucleases: Mechanisms for DNA Damage and Quinone Recycling Journal of the American Chemical Society. ,vol. 116, pp. 9847- 9859 ,(1994) , 10.1021/JA00101A005
Sandeep Kumar, Jaishri J Naidu, Sanjay K Varshney, None, Novel monofunctionalized electron-deficient anthraquinone-based discotic liquid crystals Liquid Crystals. ,vol. 30, pp. 319- 323 ,(2003) , 10.1080/0267829031000068675
Karsten Krohn, Michael Klimars, Hans-Ju¨rgen Ko¨hle, Eckehardt Ebeling, Synthesis of ζ -pyrromycinone, 7-deoxyauramycinone, and 7-deoxyaklavinone via ketoester cyclizatiON 1) Tetrahedron. ,vol. 40, pp. 3677- 3694 ,(1984) , 10.1016/S0040-4020(01)88798-6
Bruno Simoneau, Paul Brassard, A convenient synthesis of naturally occurring quinizarins Tetrahedron. ,vol. 44, pp. 1015- 1022 ,(1988) , 10.1016/S0040-4020(01)85881-6