Moustafa Ahmed GOUDA, Moged Ahmed BERGHOT, Alaa SHOEIB, Khaled M. ELATTAR, Abd El-Galil Mohamed KHALIL

Chemistry of 2-aminoanthraquinones

This review represents a systematic and comprehensive survey of the methods of preparation and the chemical reactivity of 2-aminoanthraquinone. This compound is an important intermediate for the synthesis of a variety of otherwise difficult to obtain synthetically useful and novel heterocyclic systems.

Anahtar Kelimeler:

2-Aminoanthraquinone, addition, condensation, acetylation, diazotization, macromolecules, heterocycles

Chemistry of 2-aminoanthraquinones

Keywords:

2-Aminoanthraquinone, addition, condensation, acetylation, diazotization, macromolecules, heterocycles,

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,4,5,8-Naphthalene tetracarboxylic dianhydride NDA Benzoic acid BA Isoquinoline IQ N, N -Dimethylformamide DMF Pyridinobenzanthrone PyBz ,1-Pyridinoanthraquinone ,1-PyAq Benzanthrone Bz ,6-Pyridinobenzanthrone ,6-PyBz ,8-Pyridinobenzanthrone ,8-PyBz ,3-Pyridinoanthraquinone ,3-PyAq Lehnert Reagent TiCl4/pyridine ,11,12,12-Tetracyano-9,10-anthraquinodimethane TCAQ N , N -Dimethylanilino DMA ,11,12,12-Tetracyano-9,10-anthraquinodimethane TCAQs Monogr, IARC. Eval. Carcinog. Risk Chem. Hum. 1982, 27, 191-8.
Gosselin, R. E.; Smith, R. P.; Hodge H. C.; Braddock, J. E. Clinical Toxicology of Commercial Products. Baltimore, M. D. Eds.; Williams & Wilkins, 1984.
Lewis, R. J. Sax’s Dangerous Properties of Industrial Materials. New York: Van Nostrand Reinhold, 2000.
Wynder, E. L.; Onderdonk, J.; Mantel, N. Cancer 1963, 16, 1388-1407.
Anthony, H. M.; Thomaz, G. M. England. J. Natl. Cancer Inst. 1970, 45, 879-895.
Doi, A. M.; Irwin, R. D.; Bucher, J. R. J. Toxicology and Environmental Health, Part B 2005, 8, 109-126.
Pelster, H.; Konig, C.; Putter, R.; Gleinig, H.; Bertsch, H. Patent Brit. Amended 1970, 8, 1145659.
Naeimi, H.; Namdari, R. Dyes and Pigments 2009, 81, 259-263.
Hirai, Y.; Miyata, K.; Osawa, T.; Samecima, M.; Mukai, K.; Yoshiura, K.; Mori, H. Ger. Oﬀen. 1976, 21; CA , 85, 479698.
Rauch, F. C.; Arzoumanidis, G. G. Ger. Oﬀen. 1973, 14; CA 1973, 72, 453181.
Pelster, H.; Konig, C.; Putter, R.; Gleinig, H.; Bertsch, H. Brit. Amended 1970, 8, 1145659, 19700708, CA 1972, , 101215.
Drescher, H. A. E.; Thomas, J. US Pat. 1925, 1528470, 19250303; CA 1926, 20, 3429.
Chumak, V. T.; Shein, S. M.; Bikulov, F. Kh.; Grebenyuk, V. I. U.S.S.R. 1985, 1186615, A1, 19851023; CA 1986, , 206957.
Groggins, Philip H., US Pat 1932, 1892302, 19321227; CA 1933, 27, 20731.
Groggins, P. H.; Stirton, A. J. J Industrial & Eng Chem 1933, 25, 169-75; CA 1933, 27, 14335.
Vorozhtsov, N. N.; Nikitin, V. P. Zhurnal Obshchei Khimii 1937, 7, 2080-6; CA 1938, 32, 3500.
Dokunikhin, N. S.; Egorova, L. M.; Murakhovskaya, M. A. US Pat 1949, 77400, 19491231; CA 1953, 47, 58775.
Groggins, P. H.; Stirton, A. J.; Newton, H. P. Industrial & Eng. Chem. 1931, 23 (8), 893-899.
Coulson, D. R. US Patent 1974, 5, 3832364.
Chumak, V. T.; Shein, S. M. Zhurnal Organicheskoi Khimii 1983, 19 (1), 228-9; CA 1983, 98, 143105.
Yoshida, Z.; Matsumoto, T.; Oda, R. Kogyo Kagaku Zasshi 1964, 67 (1), 70-2; CA 1964, 61, 11206.
Robson, A. C.; Coﬀey, S. J. Chem. Soc. 1954, 2372-4; CA 1955, 49, 53472
Turski, J. S. US Pat. 1952, 2585355, 19520212; CA 1953, 47, 5220.
Turski, J. S. F. GB Pat. 1949, 626661, 19490719; CA 1950, 44, 13909.
Studzinskii, O. P.; Levental, Yu. K.; Proskuryakova, T. V.; Rtishchev, N. I.; Ponomareva, R. P. U.S.S.R. Pat. , 1143741, A1 19850307; CA 1985, 103, 487667.
Uenaka, H.; Takahashi, M.; Muramoto, N.; Kotera, N. Nikkakyo Geppo 1981, 34 (12), 17-23; CA 1982, 96, 199249.
Kawasaki Kasei Chemicals, Ltd., Japan. Jpn. Kokai Tokkyo Koho, 1981, 5, 56034659, 19810406; CA 1982, 96,
Kawasaki Kasei Chemicals, Ltd., Japan, Jpn. Kokai Tokkyo Koho 1981, 5, 56020555, 19810226; CA 1982, 96,
Kniel, P. Ger. Oﬀen 1977, 10, 2646013, 19770421; CA 1977, 87, 439182.
CIBA Ltd. 1961, 2, GB 884881, 19611220; CA 1962, 57, 3890.
Loskutov, V. A.; Lukonina, S. M.; Konstantinova, A. V.; Fokin, E. P. Zhurnal Organicheskoi Khimii 1981, 17 (3), 9; CA 1981, 95, 42743.
Studzinskii, O. P.; El’tsov, A. V.; Levental, Yu. K. Zhurnal Obshchei Khimii, 1980, 50 (2), 435-40; CA 1980, 93,
Arzoumanidis, G. G.; Rauch, F. C. J. Org. Chem. 1981, 46, 3930-3932.
Rauch, F. C.; Arzoumanidis, G. G. Ger. Oﬀen. 1973, 14, 2258227, 19730607; CA 1973, 79, 453181.
Wubbels, G. G.; Tollefsen, D. M.; Meredith, R. S.; Herwaldt, L. A. J. Am. Chem. Soc. 1973, 95 (11), 3820-3822.
Phillips, M. Chem. Rev. 1929, 6 (1), 157-174.
Newport Chemical Corp. 1930, GB 370724, 19300613; CA 1933, 27, 32910.
Gubelmann, I.; Tinker, J. M. US Pat. 1933, 1910692, 19330523; CA 1933, 27, 43929.
Sander, A. DE Pat. 1924, 484432, 19241123; CA 1930, 24, 10078.
Cunningham, O. D. US Pat. 1925, 1564210, 19251208; CA 1926, 20, 3428.
Fischer, M. US Pat. 1920, 1338363, 19200427; CA 1920, 14, 9786.
Fischer, M. US Pat. 1920, 1340603, 19200518; CA 1920, 14, 10694.
(J. R. Geigy SA), GB Pat. 1919, 127223, 19190310; CA 1919, 13, 12083.
Kroupa, J.; Krulis, J.; Vrana, V.; Zemanova, D.; Cermak, J.; Albin, M.; Urbik, J.; Lasak, K. Czech. Pat. 1987, 3, , B1 19870915; CA 1988, 109, 190059.
Il’inskii, M. A.; Nikolaeva, A. N. Anilinokrasochnaya Promyshlennost 1934, 4, 564-5; CA 1935, 29, 19771.
Maki, T. Kogyo Kagaku Zasshi 1929, 32 (Suppl. binding), 344-7; CA 1930, 24, 44212.
Dutoit, P. US Pat. 1918, 1255719, 19180205; CA 1918, 12, 5540.
Matoulek, J.; Zaloudek, J.; Louda, M. Czech. Pat. 1985, 3, 218513, B1 19850315; CA 1986, 104, 109290.
Soc. Anon. Pour l’ind. Chim. Bale. 1917, CH 74747, 19170901; CA 1918, 12, 2228.
Yoshida, Z.; Matsumoto, T.; Oda, R. Kogyo Kagaku Zasshi 1964, 67 (1), 67-9; CA 1964, 61, 11205. Ullmann, F. D. R. P. 1910, 224, 982.
Anilin, B.; Fabrik, S. D. R. P. 1916, 295, 624.
Phillips, M. Ind. Eng. Chem. 1925, 17, 721.
Kazemi, F.; Kiasat, A. R.; Sayyahi, S. Phosphorus, Sulfur and Silicon and the Related Elements 2004, 179, 1813
Hida, M.; Kato, S. Kogyo Kagaku Zasshi 1962, 65, 141; CA 1963, 58, 3169.
Manabe, O.; Hirashima, T.; Noda, K.; Ikegami, S. Kokai Tokkyo Koho JP Pat. 1975, 4 ; 74-6240, 19740110; CA , 83, 206021.
Gudzenko, V. I. US Pat. 1961, 136493, 19610314; CA 1962, 56, 18210.
Seefelder, M. Ger. Pat. 1967, 4, 1245378, 19670727; CA 1968, 68, 68989.
Cee, A.; Gasparic, J. Mikrochimica Acta 1966, (1-2), 295-309; CA 1966, 65, 42626.
Hoyer, H. Zeitschrift Elektrochem. und Angew. Physikalische Chem. 1950, 54, 413-18; CA 1951, 45, 38258.
Kratochvil, N.; Nepras, M. Collect. Czechoslovak Chem. Comm. 1972, 37 (5), 1533-1538.
Cadogan, J. I. G.; Molina, G. A. J. Chem. Soc., Perkin Trans., 1973, 1 (6), 541-542.
Groggins, P. H.; Newton, H. P. Ind. Eng. Chem. 1931, 23, 893.
Groggins, P. H.; Stirton, A. J. Industrial and Engineering Chemistry 1933, 25 (2), 169-175.
Kullapere, M.; Seinberg, J.M.; Maeorg, U.; Maia, G.; Schiﬀrin, D. J.; Tammeveski, K. Electrochimica Acta 2009, , 1961-1969.
Ikemoto, N.; Liu, J. C; Brands, K. M. J.; McNamara, J. M.; Reider, P. J. Tetrahedron 2003, 59 (8), 1317-1325.
Sarhan, A. A. O.; Murakami, M.; Izumi, T. Monatsh. Chem. 2002, 133 (8), 1055-1066; CA 2002, 138, 137400.
Zarei, A.; Hajipour, A. R.; Khazdooz, L.; Aghaei, H. Tetrahedron Lett. 2009, 50 (31), 4443-4445.
Denisov, V. Y.; Tkachenko, T. B. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya Khimicheskaya Tekhnologiya , 48 (9), 99-103; CA 2006, 146, 81654.
Tkachenko, T. B.; Siyutkin, D. E. Fiziko-Khimicheskie Protsessy v Neorganicheskikh Materialakh, Mezhdunaro- dnaya Konferentsiya, 9th, Kemerovo, Russian Federation, Sept. Conference 22-25, 2004, 2, 484-485; CA 2005, , 346893.
Milner, D. J. Synthetic Comm. 1992, 22 (1), 73-82.
Bapat, D. S.; Rao, B. C. S.; Unni, M. K. and Venkataraman, K. Tetrahedron Lett. 1960, 1 (26), 15-19.
Yoﬀe, I. S.; Efros, L. S. Z. N. Z. Sheglova, Obshch. Chim. 1936, 9, 1128.
Rochlin, E.; Rappoport, Z. J. Org. Chem. 2003, 68 (2), 216-226
Vorob’eva, S. L.; Buyanov, V. N.; Levina, I. I.; Suvorov, N. N., Khimiya Geterotsiklicheskikh Soedinenii 1989, 1, 73; CA 1989, 111, 214359.
Egawa, M.; Kawakami, S.; Osaka, H.; Suzuki, T.; Nomura, R. US Pat. Appl. Publ. 2008, 122, 2008103315, A1 ; CA 2008, 148, 526318.
Hodge, P.; Power, G. A.; Rabjohns, M. A. Chem. Commun. 1997, 73-74.
Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.
Ohe, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58 (8), 2201-2208.
Baik, W.; Luan, W. Q.; Lee, H. J.; Yoon, C. H.; Koo, S.; Kim, B. H. Can. J. Chem. 2005, 83, 213-219.
Higgins, R. W.; Hilton, C. L.; Deodhar, S. D. J. Org. Chem. 1951, 16 (8), 1275-1277.
Shao, M.; Chen, G.; Zhao, Y. Synlett. 2008, 3, 371-376; CA 2008, 148, 495860.
Kopylova, T. M.; Popov, S. I.; Braude, E. V.; Andrievskii, A. M. Russ. J. Org. Chem. 1993, 29, 898.
Carothers, W. H.; Collins, A. M.; Kirby, J. E. J. Am. Chem. Soc. 1933, 55, 786-788.
Popov, S. I.; Kopylova, T. M.; Andrievskii, A. M.; Medvedev, S. V.; Yatsenko, A. V. Russ. J. Org. Chem. 1994, , 279-285.
Baik, W.; Luan, W.Q.; Lee, H. J.; Yoon, C. H.; Koo, S.; Kim, B. H. Canadian J. Chem. 2005, 83 (3), 213-219. CA 2005, 143, 77894.
Abou-Elkhair, R. A. I.; Netzel, T. L. Nucleosides, Nucleotides, and Nucleic Acids 2005, 24 (2), 85-110.
Gorodetsky, A. A.; Green, O.; Yavin, E.; Barton, J. K. Bioconjugate Chem. 2007, 18, 1434-1441.
Criswell, T. R.; Klanderman, B. H. J. Org. Chem. 1974, 39, 770-774.
Coleman, R. S.; Mortensen, M. A. Tetrahedron Lett. 2003, 44 (6), 1215-1219.
(a) Cameron, M. A.; Cush, S. B.; Hammer, R. P. J. Org. Chem. 1997, 62, 9065-9069; (b) Larson, E.; Jorgensen,
P. T.; Sofan, M. A.; Pederson, E. B. Synthesis 1994, 1037-1038.
Coleman, R. S.; Madaras, M. L. J. Org. Chem. 1998, 63, 5700-5703.
Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
Lee, L.-T.; Yeh, J.-B. US Pat. Appl. Publ. 2003, 9, 2003,149092,0807; CA 2003, 139, 164633.
Franc, J. V.; Koudelkova, V. J. Chromatography 1979, 170, 89-97.
Sondhi, S. M.; Sharma, V. K.; Singhal, N.; Verma, R. P.; Shukla, R.; Raghubir, R.; Dubey, M. P. Phosphorus, Sulfur & Silicon and the Rel. Elements 2000, 156, 21-33.
Nandi, B. K.; Ganapathi, K. Current Science 1940, 177.
Arai, S.; Yamagishi, T.; Hida, M. Chem. Lett. 1981, 1789-1792.
Arai, S.; Kato, S.; Hida, M. Bull. Chem. Soc. Jpn 1985, 58, 1458-1463.
Slavik, V.; Arient, J. Res. Inst. Org. Synth. Czech. Coll. Czech. Chemical Comm. 1975, 40 (4), 1193-8; CA 1975, , 61607.
Sui, B.; Fu, X. Dyes and Pigments 2009, 83, 1-6.
Chabane, H.; Pierre, A.; Leonce, S.; Pfeiﬀer, B.; Renard, P.; Thiery, V.; Guillaumet, G.; Besson, T. J. Enzyme Inhib. & Med. Chem. 2004, 19 (6), 567-575.
Getautis, V.; Dashkyavichene, M.; Paulauskaite, I.; Stanisauskaite, A. Chem. of Heterocycl. Compounds 2005, 41 (4), 426-436
Crowhurst, L.; Lancaster, N. L.; P´erez Arlandis, J. M.; Welton, T. J. Am. Chem. Soc. 2004, 126, 11549-11555.
Yavari, I.; Kowsari, E. Tetrahedron Lett. 2007, 48, 3753-3756.
Javed, T.; Shattat, G. F. J. Heterocyclic Chem. 2005, 42 (2), 217-220.
Denisov, V. Y.; Tkachenko, T. V.; Grechneva, S. A. Khimiya Khimicheskaya Tekhnologiya 2002, 45 (6), 39-42;
Gregoire, P. J.; Mellor, J. M.; Merriman, G. D. Tetrahedron 1995, 51 (21), 6133-6144.
Yavari, I.; Kowsari, E. J. Sulfur Chem. 2008, 29 (5), 529-537.
Desai, R. D.; Dalal, S. K.; Parikh, A. R. J. Institution of Chem. (India) 1990, 62 (1), 16-18; CA 1991, 114, 25800.
Drogovoz, S. M.; Slyshkov, V. V.; Ranhel Sanches, E.; Bezuglyi, P. A.; Shtefan, L. M.; Brigida, N. V. Farmat- sevtichnii Zhurnal (Kiev) 1992, 4, 43-7; CA 1993, 118, 101629.
Sankaranarayanan, A.; Raman, G.; Busch, C.; Schultz, T.; Zimin, P. I.; Hoyer, J.; Kohler, R.; Wulﬀ, H. Molecular Pharmacol. 2009, 75 (2), 281-295.
Tatke, D. R.; Seshadri, S. Ind. J.Chem B. 1983, 22B, 1197-1199.
Singh, I. P.; Saxena, A. K.; Shanker, K. Ind. J. Chem. B 1986, 25, (8), 838-843.
Sal’nikov, S. I.; Ilyna, T. V.; Zhuravlev, N. S.; Verdyan, A. I. Pharmaceutical Institute, Khar’kov. Translated from Khimiko-farmatsevticheskii Zhurnal 1990, 24 (5), 25-27.
Helferich, B.; Zeid, I. J. Praktische Chem. 1968, 38 (1-2), 40-9; CA 1968, 69, 96118.
Wan, J. D.; Ferreira, A.; Xia, W.; Chow, C. H.; Takechi, K.; Kamat, P. V.; Jones, G.; Vullev, V. I. J. Photochem. & Photobiology, A: Chem. 2008, 197 (2-3), 364-374.
Jin, G.; Lu, D.; Yao, S.; Wu, C. C. N.; Liu, J. X.; Carson, D. A.; Cottam, H. B. Bioorg. & Med. Chem. Lett. 2009, (3), 606-609.
Shangguan, G. Q.; Huang, L. L.; Qu, X. G. Chinese Chem. Lett. 2007, 18 (11), 1347-1350. CA 2007, 150, 191578.
Yu, C.-P.; Tai, C.-L. Faming Zhuanli Shenqing Gongkai Shuomingshu Pat 1758459, 2006,0412, 19; CA 2006, 145,
Vorobeva, S. L.; Berzina, T. S. J. Chem. Soc., Perkin Trans. 2: Physical Org. Chem. (1972-1999) 1992, 7, 1133-6; CA 1992, 117, 170928.
Berghot, M. A.; Hanna, M. A.; Girges, M. M. Pharmazie 1992, 47 (5), 340-343.
Wannalerse, B.; Tuntulani, T.; Tomapatanaget, B. Tetrahedron 2008, 64, 10619-10624.
Lee, L. V.; Mitchell, M. L.; Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. J. Am. Chem. Soc. 2003, (32), 9588-9589.
Venkataraman, K. The Chemistry of Synthetic Dyes [Russian translation], Gos. Khim. Izdat., Leningrad 1957, 2,
Litvinova, L. A.; Lyakhov, S. A.; Andronati, S. A.; Zhukova, N. A.; Yasinskaya, O. G.; Galkin, B. N.; Filippova, T. O.; Golovenko, N. Ya. Pharm. Chem. J. 1998, 32 (12).
Loskutov, V. A.; Savel’ev, V. A.; Konstantinova, A. V. Novosib. Seriya Khimicheskikh Nauk 1985, 3, 114-18; CA
Bhavsar, S. B.; Shah, R. G.; Parikh, A. R. J. of the Institution of Chemists (India) 1991, 63 (3), 101-102.
Mehdipour-Ataei, S.; Arabi, H.; Bahri-Laleh, N. Eur. Polymer J. 2006, 42, 2343-2351.
Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Parris, K.; Williams, K.; Rebek, J. J. Am. Chem. Soc. , 111, 1082-1090.
Park, T. K.; Schroeder, J.; Rebek, J. J. Am. Chem. Soc. 1991, 113 (13), 5125-5127; CA 1991, 115, 449227.
Herranz, M. A.; Martin, N.; Campidelli, S.; Prato, M.; Brehm, G.; Guldi, D. M. Angew. Chem. 2006, 45 (27), 4482; CA 2006, 145, 324786.
Atanasoaie, D.; Iscrulescu, L.; Sebe, I. Chem. and Materials Sci. 2005, 67 (2), 41-48; CA 2006, 146, 102313.
Badische, A. U.; Fabrik, S. German patent 238,158; Frdl. 1910, 10, 722.
Farbenindustrie I. G.; A. G. German patent 590, 613; Frdl. 1934, 19, 2045.
Schaarschmidt, A. Ann. 405, 102. Allen, C. F. H. Chem. Rev. 1959, 59 (6), 983-1030.
Badische, A. U.; Fabrik, S. German patent 248, 582; Frdl. 1912-14, 11, 676.
Ullmann, F.; Sone, M. Ann. 1911, 380, 336.
Dobrescu, D.; Berindei, A. Rom. Pat. 1987, 3, 92446, 0930; CA 1991, 114, 187563.
Kobayashi, N.; Nishiyama, Y.; Oya, T.; Sato, M. J. Chem. Soc., Chem. Comm. 1987, 5, 390-2; CA 1988, 108,
Yu, C.; Ke, C. Faming Zhuanli Shenqing Gongkai Shuomingshu Pat 2005, 15, 1583691, 0223; CA 2005, 143,
Soleiman, H. A. Chem. Pap., 2004, 58 (5), 330-333.
Pandit, P. N.; Tilak, B. D.; Venkataraman, K. Proc. Indian Acad. Sci. 1950, 32, 39.
Bradley, W.; Sutcliﬀe, F. K. J. Chem. Soc. 1952, 2118.
Sawada, T.; Ishii, H.; Ueda, T.; Iwashima, S. Polycyclic Aromatic Compounds 2006, 26, 121-144. a) Lehnert, W. Synthesis, 1974, 667-669; b) Lehnert, W. Tetrahedron Lett. 1970, 11, 4723-4724.
Bures, F.; Schweizer, W. B.; Boudon, C.; Gisselbrecht, J. P.; Gross, M.; Diederich, F. Eur. J. Org. Chem. 2008, 1004.
Nishizawa, Y.; Suzuki, T.; Yamashita, Y.; Miyashi, T.; Mukai, T. Nippon Kagaku Kaishi 1985, 5, 904-9; CA 1986, , 68550.
Gudzenko, V. I.; Leichenko, L. D. USSR Pat. 1974, 436819, 0725; CA 1974, 81, 135824.
Moroz, A. A.; Beloborodova, I. A. Zhurnal Organicheskoi Khimii 1981, 17 (12), 2612-16; CA 1982, 96, 122376.
Singh, M. R.; Shah, K. H. Indian J. Chem., Sec. B: Org. Chem. Including Med. Chem. 1978, 16 B(2), 100-2; CA , 89, 112272.
Hamilton, K.; Hunter, J. A.; Preston, P. N.; Morley, J. O. J. Chem. Soc., Perkin Trans. 2: Physical Org. Chem. (1972-1999), 1980, 10, 1544-8; CA 1981, 94, 29802.
Yoshida, K.; Hikasa, M.; Ishii, K.; Kadota, H.; Yamashita, Y. J. Chem. Soc., Chem. Comm. 1986, 10, 758-9; CA , 106, 18060.
Tanaka, Y.; Oki, Y.; Ishii, Y. Sen’i Gakkaishi 1968, 24, 132-9; CA 1968, 69, 44549.
Pauling, L. The Nature of the Chemical Bond. Ithaca: Cornell Univ. Press 1960, 262.
Janczak, J. Acta Cryst. C, 1995, 51, 1381-1382.
Johnson, J., Lanman-Ludwig, D., Athey, P., Singer, A., Graves, S., Hejtmancik, M. 1999. Final report on “Special day dosed-feed study of anthraquinone (CAS No. 84-65-1) in Fisher 344 rats (G234573-A)” to the National
Institute of Environmental Health Sciences, Battelle, Columbus, OH. Sato, T., Fukuyama, T., Yamada, M., Suzuki, T. J. Biochem. 1956, 43, 21-24. Sims, P. Biochem. J. 1964, 92, 621-631.
Sipes, I. G., Carter, D. E., Winter, S. M., Zheng, W. Chemical disposition in mammals: Disposition of an- thraquinone in the male Fischer 344 rat. Final report to the NIEHS, the National Toxicology Program, Research Triangle Park, NC. Department of Pharmacology and Toxicology, College of Pharmacy, University of Arizona, Tucson, AZ, 1993.
Doi, A. M.; Irwin, R. D.; Bucher, J. R. J. Toxicology & Environmental Health, Part B, 2005, 8, 109-126.
Palumbo, M., Palu, G., Gia, O., Ferrazzi, E., Gastaldi, S., Antonello, C., Meloni, G. A. Anticancer Drug Des. , 1, 337-46. Tanious, F. A., Jenkins, T. C., Neidle, S., Wilson, W. D. Biochemistry 1992, 31, 11632-11640.
Keppler, M. D., Read, M. A., Perry, P. J., Trent, J. O., Jenkins, T. C., Reszka, A. P., Neidle, S., Fox, K. R. Eur. J. Biochem. 1999, 263, 817-25.
Ashnagar, A., Bruce, J. M., Dutton, P. L., Prince, R. C. Biochim. Biophys. Acta 1984, 801, 351-359.
Tarasiuk, J., Liwo, A., Wojtkowiak, S., Dzieduszycka, M., Tempczyk, A., Garnier-Suillerot, A., Martelli, S., Borowski, E. Anticancer Drug Des. 1991, 6, 399-416.
Pawlowska, J., Tarasiuk, J., Wolf, C. R., Paine, M. J., Borowski, E. Oncol. Res. 2003, 13, 245-52.
Gothoskar, S. V., Benjamin, T., Roller, P. P., Weisburger, E. K. Cancer Detect. Prev. 1979, 2, 485-494.
Duﬀel, M. W. Chem. Biol. Interact. 1994, 92, 3-14.
Klaassen, C. D., Liu, L., Dunn, R. T. Chem. Biol. Interact. 1998, 109, 299-313.
Lueoend, R. M.; McKie, J. H.; Douglas, K. T.; Dascombe, M. J.; Vale, J. J. Enz. Inhibition, 1998, 13 (5), 327-345; CA 1998, 129, 213388.
Sheu, S.-Y.; Chiang, H.-C. Anticancer Research 1997, 17 (5A), 3293-3297; CA 1998, 128, 162541.
Weimer, P. J.; Odom, J. M.; Cooling, F. B., U.S. Pat 1995, 22, 5385842, A 19950131; CA 1995, 122, 321744.
Resources, USA. U.S. Pat 1996, 7, 5500368, A 19960319; CA 1996, 124, 297885.
Tatnall, R. E. Eur. Pat. Appl. 1994, 11, 591000, 19940406; CA 1994, 120, 263849.
Anderson, A. G.; Cooling, F. B., PCT Int. Appl. 1991, 93, 9115954, 19911031; CA 1992, 116, 148128.
Tanaka, T.; Metori, K.; M., Satoshi; M., Hitoshi; S., T. Yakugaku Zasshi 1990, 110 (9), 688-92; CA 1991, 114,
Sankaranarayanan, A.; Raman, G.; Busch, C.; Schultz, T.; Z., Pavel I.; Hoyer, J.; Kohler, R.; Wulﬀ, H. Molecular Pharmacology 2009, 75 (2), 281-295.
Jin, G.; Lu, Desheng; Y., Shiyin; W., Christina C. N.; Liu, J. X.; Carson, D. A.; Cottam, H. B. Bioorg. & Med. Chem. Lett. 2009, 19 (3), 606-609.
Dikov, A.; Dimitrova, M.; Krieg, R.; Halbhuber, K.-J. Cellular & Mol. Biology 2004, 50, OL553-OL558; CA 2005, , 128816.
Dikov, A.; Dimitrova, M.; Krieg, R.; Halbhuber, K.-J. Cellular & Mol. Biology 2004, 50, OL565-OL568; CA 2005, , 128817.
Lee, L.-T.; Yeh, J.-B. U.S. Pat. Appl. Publ. 2003, 9, 2003149092, 20030807; CA 2003, 139, 164633.
Qu, X.; Shangguan, G. Faming Zhuanli Shenqing Gongkai Shuomingshu 2006, 12, 1715284, 20060104; CA 2006, , 103843.
Sondhi, S. M.; Sharma, V. K.; Singhal, N; Verma, R. P.; Shukla, R.; Raghubir, R.; Dubey, M. P. Phosphorus, Sulfur and Silicon and the Related Elements 2000, 156, 21-33.
Sal’nikova, S. I.; Il’ina, T. V.; Zhuravlev, N. S.; Verdyan, A. I. Khimiko-Farmatsevticheskii Zhurnal 1990, 24 (5), 7; CA 1990, 113, 204406.
Singh, I. Pal; Saxena, A. K.; Shanker, K. Indian J. Chem., Sec. B: Org. Chem. Including Med. Chem. 1986, 25 B(8), 838-43; CA 1987, 107, 175921.
Drogovoz, S. M.; Slyshkov, V. V.; Ranhel Sanches, E.; Bezuglyi, P. A.; Shtefan, L. M.; Brigida, N. V. Farmat- sevtichnii Zhurnal (Kiev) 1992, 4, 43-7; CA 1993, 118, 101629.
Drogovoz, S. M.; Slyshkov, V. V.; Ranhel S., E.; Bezuglyi, P. A.; Shtefan, L. M.; Brigida, N. V. Farmatsevtichnii Zhurnal (Kiev) 1992, 4, 43-7; CA 1993, 118, 101629.
Teijeira, M.; Santana, L.; Uriarte, E.; Jorge, M. L.; Seoane, R. Farmaco 1996, 51 (6), 447-450; CA 1996, 125,
Berghot, M. A.; Hanna, M. A.; Girges, M. M. Pharmazie 1992, 47 (5), 340-3; CA 1992, 117, 150945.
Park, Sung Hui. Repub. Korean Kongkae Taeho Kongbo Pat. 2006, 2006043923, 20060516; CA 2006, 146, 360617.
Javed, T.; Shattat, G. F. J. Heterocyclic Chem. 2005, 42 (2), 217-220.
Park, S. H. Repub. Korean Kongkae Taeho Kongbo Pat. 2006, KR 2006043923, 20060516; CA 2006, 146, 360617.
Patel, K. C.; Patel, S. K.; Patel, B. V.; Desai, K. R. J. Indian Chem. Soc. 1997, 74 (6), 518-519; CA 1997, 127,
Patel, K. C.; Patel, S. K.; Patel, B. V.; Desai, K. R. J. Indian Chem. Soc. 1997, 74 (6), 518-519; CA 1997, 127,
Saiga, T.; Yada, T.; Shimizu, T.; Honda, K. Jpn. Kokai Tokkyo Koho 1988, 6, 63068553, 0328; CA 1988, 109,
Li, H. Y.; Lei L. C. Synth. Comm. 2001, 31 (1), 155-158.
Kraska, J.; Truszkowska, I. Politechnika Lodzka, Pol. Pat 1978, 3, PL 98871, 19781030; CA 1979, 91, 194618.
Ueno, R.; Ito, S.; Minami, K.; Kitayama, M. U.S. Pat. 1998, 51, 5786523, A 19980728; CA 1998, 129, 148831.
Desai, R. D.; Dalal, S. K.; Parikh, A. R. J. Institution Chem. (India) 1990, 62 (1), 16-18; CA 1991, 114, 25800.
Kalopissis, G.; Bugaut, A. U.S. Pat. 1980, 9, 4226784, 19801007; CA 1981, 94, 52695.
Vacek, O.; Marval, E. Pat. 1959, CS 90136, 19590515; CA 1961, 55, 40427.
Kim, H.-Y.; Yang, S.-G.; Shin, J.-H.; Lee, J.-Y. U.S. Pat. Appl. Publ. 2009, 35, US 2009256473, A1 20091015; CA
Yang, S.-G.; Kim, H.-Y.; Lee, J.-Y.; Lee, J.-H. U.S. Pat. Appl. Publ. 2010, 45, 2010039029, A1 20100218; CA , 152, 299630.
Kim, H.-Y.; Yang, S.-G.; Shin, J.-H.; Lee, C.-H.; Ko, H.-J. Eur. Pat. Appl. 2008, 32, 1925618, A1 20080528; CA , 148, 596244.
Kim, K.-K.; Jang, H.-Y.; Hong, S.-K.; Yeo, S.-J.; Jeon, S.-Y. PCT Int. Appl. 2007, 115, 2007058503, A1 20070524,
Yu, C. P.; Tai, C.L. Faming Zhuanli Shenqing Gongkai Shuomingshu 2006, 19, 1758459, A 20060412; CA 2006, , 220748.
Je, J. T.; Lee, S. H.; Ryu, G. U.; Lee, S. J.; Song, B. G. Repub. Korean Kongkae Taeho Kongbo Pat. 2010, 32, KR 2010021351, A 20100224; CA 2010, 255141.
Kawakami, S.; Suzuki, T.; Ohsawa, N.; Shitagaki, S.; Seo, S. PCT Int. Appl. 2009, 231, 2009131199, A1 20091029; CA 2009, 151, 517741.
Kawakami, S.; Ohsawa, N.; Seo, S. Eur. Pat. Appl. 2009, 60, EP 2009-4367, 20090326; CA 2009, 151, 499858.
Buesing, A.; Heil, H.; Stoessel, P. PCT Int. Appl. 2009, 85, 2009-EP1938, 0317; CA 2009, 151, 461009.
Buesing, A.; Stoessel, P.; Heil, H. Ger. Oﬀen. 2009, 55, 102008018670, A1 20091015, CA 2009, 151, 460848.
Kawakami, S.; Suzuki, T.; Ohsawa, N.; Shitagaki, S.; Seo, S. Eur. Pat. Appl. 2009, 84, EP 2107096, A2 20091007; CA 2009, 151, 436591.
Lee, D. H.; Kim, Y. H.; Ham, Y. H.; Kim, G. G.; Lee, J. C.; Kim, S. S. Repub. Korean Kongkae Taeho Kongbo , 84, KR 2009079133, A 20090721; CA 2009, 151, 275915.
Jang, H. Y.; Kim, G. G.; Kim, J. E.; Park, T. Y.; Lee, J. C.; Jung, D. S. Repub. Korean Kongkae Taeho Kongbo , 49, KR 2009052774, A 20090526; CA 2009, 151, 56618.
Ushikubo, T. U.S. Pat. Appl. Publ. 2009, 58, 2009085479, A1 20090402, CA 2009, 150, 385530.
Ushikubo, T.; Seo, S. Eur. Pat. Appl. 2009, 221, EP 2031036, A1 20090304; CA 2009, 150, 294220.
Kim, H. Y.; Yang, S. G.; Shin, J. H.; Lee, C. H.; Ko, H. J. Repub. Korea Pat. 2008, 19, KR 852118, B1 20080813, CA 2008, 149, 365867.
Egawa, M.; Kawakami, S.; Osaka, H.; Suzuki, T.; Nomura, R. U.S. Pat. Appl. Publ. 2008, 122, 2008103315, A1 ; CA 2008, 148, 526318.
Kim, J.-E.; Lee, J.-C.; Jang, H.-Y.; Park, T.-Y.; Hong, S.-K.; Jang, J.-G.; Park, J.-K.; Nam, H.; Kim, K.-K.; Kim, Y.-H. PCT Int. Appl. 2008, 36, 2008013399, 20080131, CA 2008, 148, 225191.
Yeo, S.-J.; Kim, K.-K.; Jang, H.-Y. PCT Int. Appl. 2007, 75, 081179, A1 0719; CA 2007, 147, 176707.
Kim, K.-K.; Jang, H.-Y.; Hong, S.-K.; Yeo, S.-J.; Jeon, S.-Y. PCT Int. Appl. 2007, 115, 058503, 0524, CA 2007, , 530902.
Kawamura, M.; Hosokawa, C. PCT Int. Appl. 2006, 73, 067931, A1 0629; CA 2006, 145, 103730.
Yu, C.-P.; Ko, C.-W. U.S. Pat. Appl. Publ. 2005, 14, 260442, A1 1124, CA 2005, 143, 469214.
Yu, C.; Ke, C. Faming Zhuanli Shenqing Gongkai Shuomingshu Pat. 2005, 15, 1583691, A 0223; CA 2005, 143,
Kawamura, M.; Yamamoto, H.; Hosokawa, C. PCT Int. Appl. 2005, 95, 097756, A1, 1020; CA 2005, 143, 405909.
Diaz, M. C.; Illescas, B. M.; Seoane, C.; Martin, N. J. Org. Chem. 2004, 69 (13), 4492-4499.
Kim, J.-E.; Son, S.-H.; Bae, J.-S.; Lee, Y.-G.; Kim, K.-K.; Lee, J.-C.; Jang, J.-G.; Im, S.-G. PCT Int. Appl. 2003, , 2003095445, A1 20031120; CA 2003, 139, 388293.
Jin, M.; Yang, Q. X.; Lu, R.; Pan, L. Y.; Qi, W. Y.; Zhao, Y. Y. Materials Chem. & Physics 2003, 82 (1), 246-252.
Langhals, H.; Saulich, S. Ger. Oﬀen. 2003, 36, DE 10212358, A1 20031002; CA 2003, 139, 278003.
Langhals, H.; Saulich, S. Chem. Eur. J. 2002, 8 (24), 5630-5643.
Hayata, H.; Kinoshita, A.; Shibata, T.; Suzuki, T. Jpn. Kokai Tokkyo Koho 1997, 17 JP 09068819, A 19970311; CA 1997, 126, 310439.
Mehdipour-Ataei, S.; Bahri-Laleh, N. Polymers for Advanced Technologies 2008, 19 (4), 291-298.
Mehdipour-Ataei, S.; Arabi, H.; Bahri-Laleh, N. Eur. Polymer J. 2006, 42 (10), 2343-2351.
Lee, S. B.; Yang, J. S.; Park, D. K. Polymer (Korea) 2001, 25 (4), 496-502; CA 2001, 135, 289146.
Dreyfus, T.; Marechal, E. Bull. Soc. Chim. de France 1975, 5-6, Pt. 2, 1196-200; CA 1975, 83, 195198.
Vorobeva, S. L.; Berzina, T. S. J. Chem. Soc., Perkin Trans. 2: Physical Org. Chem. (1972-1999) 1992, 7, 1133-6; CA 1992, 117, 170928.
Murer, P.; Lewandowski, K.; Svec, F.; Frechet, J. M. Chem. Commun. 1998, 23, 2559-2560.
Umeda, T.; Tsujii, M.; Watanabe, A. Jpn. Kokai Tokkyo Koho 2000, 9, JP 028823, A 0128; CA 2000, 132, 123420.