3504
P. H. KUMAR ET AL.
the compound 1, which was filtered and dried (3.4 g, 97.1%); mp > 300 ꢀC
(Decomposition); IR (KBr) tmax 3400, 3305, 1570, 1516, 1207, 833, 551, 455,
cmꢁ1
;
1H NMR (200 MHz, DMSO-d6); d 7.14 (2H, d, J ¼ 10 Hz), 7.28 (2H, d,
J ¼ 10 Hz), 7.94 (4 H, brs), 12.78 (2 H, s).
ACKNOWLEDGMENTS
The authors thank Dr. Anil Kush, CEO, Vittal Mallya Scientific Research
Foundation, for his encouragement and Mr. A. C. Karunakara for analytical support.
REFERENCES
1. Zee-Cheng, R.; Cheng, C. C. Antineoplastic agents. Structure-activity relationship study
of bis(substituted aminoalkylamino) anthraquinones. J. Med. Chem. 1978, 21, 291–294;
(b) Xu, P.; Xiao, S.; Liao, Y. Synthesis of antineoplastic agent DHAQ. Sichuan Yixueyuan
Xuebao 1985, 16(2), 105–108; Chem. Abstr. 1986, 104, 129592; (c) Chang, P. Synthesis and
characterization of anticancer anthraquinones: Ametantrone and mitoxantrone. Part A.
Phys. Sci. Eng. 1992, 16(4), 304–310; Chem. Abstr. 1993, 119, 116918.
2. (a) Stilmar, F. B.; Perkins, M. A. The Chemistry of Synthetic Dyes and Pigments;
Reinhold: New York, 1955, p. 337; (b) Krenmueller, F.; Till, H.; Stoll, P. Aminoanthra-
quinones. DE 2340114, 1974; Chem. Abstr. 1974, 80, 133125t; (c) Greenhalgh, C. W.;
Hughes, N. The reaction of leucoquinizarins with alkylenediamines. J. Chem. Soc. C
1968, 1284–1288.
3. (a) Chandregowda, V.; Kush, A. K.; Reddy, G. C. Synthesis and in vitro antitumor activi-
ties of novel 4-anilinoquinazoline derivatives. Eur. J. Med. Chem. 2009, 44, 3053–3062; (b)
Chandregowda, V.; Kush, A. K.; Chandrasekara Reddy, G. Synthesis of benzamide deri-
vatives of anacardic acid and their cytotoxic activity. Eur. J. Med. Chem. 2009, 44,
2711–2719.
4. Hederich, V.; Klemm, K.; Gehrke, G. Anthraquinone dyes for polyester fibers. DE
1180760, 1964; Chem. Abstr. 1965, 62, 6605.
5. Mitsubishi Chemical Industries Co., Ltd., Japan. Manufacture of anthraquinone dyes. JP
56163151, 1981; Chem. Abstr. 1982, 96, 124524.
6. Kurosawa, M.; Imai, H. Anthraquinone dyes for polyesters. JP 45032548, 1970; Chem.
Abstr. 1971, 74, 88662.
7. Yamada, E.; Hamaguchi, K.; Akamatsu, T. 1,8-Dihydroxy-4,5-diaminoanthraquinone
halides. JP 46010080, 1971; Chem. Abstr. 1971, 75, 110985.
8. Takeshita, A.; Sunami, M. Diaminodihydroxyanthraquinone. JP 52107027, 1977; Chem.
Abstr. 1978, 88, 37506.
9. Kimura, Y.; Ban, K.; Kawashima, O. Diaminodihydroxyanthraquinone. JP 53056649,
1978; Chem. Abstr. 1978, 89, 129320.
10. Morley, J. O.; Hutcheson, R. Reduction of hydroxynitroanthraquinones or their alky-
lether or sulfonic acid derivatives to the corresponding amino compounds. DE 2810484,
1978; Chem. Abstr. 1979, 90, 22683.
11. Morley, J. O.; Hutcheson, R. Catalyzed hydrogenation of hydroxynitroanthquinones in
strong acid. J. Chem. Tech. Biotech. 1980, 30(8), 409–414; Chem. Abstr. 1981, 94, 85651.
12. Jablonski, J.; Gogolewski, S.; Norek, A. Manufacture of 1,8-dihydroxy-4,5-
diaminoanthraquinone and=or 1,5-dihydroxy-4,8-diaminoanthraquinone. PL 140698,
1987; Chem. Abstr. 1988, 109, 212379.
13. Dobrovolny, J.; Pokormy, M.; Tichy, J. Method of preparing diaminodihydroxyanthra-
quinone derivatives. CS 240795, 1987; Chem. Abstr. 1989, 110, 38767.