Literature cited
I. Baxter and B. A. Davis, Quart. Rev., 239 (1971).
Yu. S. Tsizin, Khim. Geterotsikl. Soedin., 593 (1978).
R. H. Thomson, Naturally Occurring Quinones, London (1971).
J. S. Webb, D. B. Cosulich, et al., J. Am. Chem. Soc.,84, 3185 (1962).
E. F. Gale, E. Cundliffe, P. E. Reynolds, et. al., Molecular Foundations of the Action of Antibiotics [Russian translation], Moscow (1975), p. 276.
H. W. Moore, Science,197, 572 (1977).
T. Kametani and K. Takahashi, Heterocycles,13, 411 (1979).
F. Nakatsubo, A. J. Cocuzza, F. J. Keely, et al., J. Am. Chem. Soc.,99, 4835 (1977).
F. Nakatsubo, T. Fukuyama, A. J. Cocuzza, et al., J. Am. Chem. Soc.,99, 8115 (1977).
T. Fukuyama, F. Nakatsubo, A. J. Cocuzza, et al., Tetrahedron Lett., 4295 (1977).
K. Nakano, Heterocycles,13, 373 (1979).
T. S. Safonova, Zh. Vses. Khim. Ova. imeni D. I. Mendeleev,18, 657 (1973).
K. V. Rao, K. Biemann, and R. B. Woodward, J. Am. Chem. Soc.,85, 2532 (1963).
E. F. Gale, E. Cundliffe, P. E. Reynolds, et al., Molecular Foundations of the Action of Antibiotics [Russian translation], Moscow (1975).
J. Haidu and E. S. Armstrong, J. Am. Chem. Soc.,103, 232 (1981).
F. Z. Basha et al., J. Am. Chem. Soc.,102, 3962 (1980).
T. K. Liao, W. H. Nyberg, and C. C. Cheng, J. Heterocycl. Chem.,13, 1063 (1976).
T. Kametani, A. Kozuka, and T. Terui, J. Pharm. Soc. Jpn.,93, 408 (1973).
A. S. Kende, Heterocycles,6, 1485 (1977).
A. S. Kende and P. C. Nagely, Tetrahedron Lett., 4775 (1978).
K. V. Rao, Cancer Chemother. Rep., Part 2,4, 11 (1974).
K. V. Rao, J. Heterocycl. Chem.,14, 653 (1977).
H. Mishima, H. Fukumi, and H. Kurihara, Heterocycles,6, 1652 (1977).
H. Fukumi, H. Kurihara, and H. Mishima, Chem. Pharm. Bull.,29, 2175 (1978).
H. Fukumi et al., Tetrahedron Lett., 3825 (1977).
A. Kubo et al., Tetrahedron Lett., 3207 (1980).
T. Arai and T. Katsuhiro, Tetrahedron Lett., 2355 (1979).
J. Sygurch, F. Brisse, and S. Hanessian, Tetrahedron Lett., 4021 (1974).
S. Danishefsky et al., Tetrahedron Lett., 4819 (1980).
S. Omura et al., Chem. Pharm. Bull.,21, 931 (1973).
G. P. Arsenault, Tetrahedron Lett., 4033 (1965).
D. W. Cameron, K. R. Deutscher, and G. I. Feutrill, Tetrahedron Lett., 5089 (1980).
A. J. Birch et al., J. Chem. Soc., Perkin Trans. I, 807 (1979).
A. J. Birch and T. J. Simpson, J. Chem. Soc., Perkin Trans. I, 816 (1979).
R. E. Effenberger and T. J. Simpson, J. Chem. Soc., Perkin Trans. I, 823 (1979).
R. A. Nicolaus, Melanins, Paris (1968).
S. P. Lyakh and E. L. Ruban, Microbial Melanins [in Russian], Moscow (1972).
Y. Omote and T. Komatsu, J. Chem. Soc., Chem. Commun., 792 (1974).
L. Slechta, C. G. Chidester, and F. Reusser, J. Antibiot.,33, 919 (1980).
H. Hoeksema and W. C. Krueger, J. Antibiot.,29, 704 (1976).
H. Tanaka et al., J. Antibiot.,28, 868 (1975).
S. Omura, T. Tanaka, J. Okada, et al., J. Chem. Soc., Chem. Commun., 320 (1976).
Y. Iwai et al., J. Antibiot.,31, 959 (1978).
N. Tsuji, M. Kobayashi, Y. Terui, et al., Tetrahedron,32, 2207 (1976).
M. Kasai et al., J. Antibiot.,32, 442 (1979).
G. A. Ellestad et al., J. Am. Chem. Soc.,90, 1325 (1968).
T. T. Li and R. H. Ellison, J. Am. Chem. Soc.,100, 6263 (1978).
A. Ichihara et al., Tetrahedron Lett., 4469 (1980).
G. A. Kraus and B. Roth, J. Org. Chem.,43, 4923 (1978).
R. G. Werner et al., J. Antibiot.,32, 1104 (1979).
H. Tanaka, Tetrahedron Lett., 4359 (1980).
R. G. F. Giles and G. H. P. Roos, J. Chem. Soc., Perkin Trans. I, 1632 (1976).
N. K. Kapoor, R. B. Gupta, and R. N. Khanna, Tetrahedron Lett., 5083 (1980).
J. K. McLeod, B. R. Worth, and R. J. Wells, Aust. J. Chem.,31, 1553 (1978).
R. D. Allan, R. L. Corell, and R. J. Wells, Tetrahedron Lett., 4669 (1969).
R. D. Allan, R. W. Dunlop, M. J. Kendall, et al., Tetrahedron Lett., 3 (1973).
J. K. McLeod, B. R. North, and R. J. Wells, Aust. J. Chem.,31, 1545 (1978).
H. Kakisawa, T. Hayashi, J. Okazaki, et al., Tetrahedron Lett., 3231 (1968).
H. Kakisawa, T. Hayashi, and T. Yamazaki, Tetrahedron Lett., 301 (1969).
R. H. Thomson, Naturally Occurring Quinones, London (1971).
J. W. Cornforth, J. D. Bullock, and D. Bright, J. Chem. Soc., C, 2786 (1971).
D. Tresselt, K. Echardt, and W. Ihn, Tetrahedron,34, 399, 2693 (1978).
H. Brockman and A. Zeeck, Chem. Ber.,103, 1709 (1970).
J. W. Cornforth, J. D. Bullock, and D. Bright, J. Chem. Soc., C, 2786 (1971).
T. Kato, N. Katagiri, J. Nakano, et al., J. Chem. Soc., Chem. Commun., 645 (1977).
D. H. Barton et al., J. Chem. Soc., Perkin Trans. II, 499 (1976).
V. Pasupathy et al., Chem. Ber.,108, 3675 (1975).
H. Hoeksema, C. Chidester, S. A. Mizsak, et al., J. Antibiot.,31, 1067 (1978).
H. Hoeksema et al., J. Antibiot.,32, 773 (1979).
Y. Iwai et al., J. Antibiot.,33, 1114 (1980).
P. Sensi, M. T. Timbal, and G. Maffii, Experientia,16, 412 (1960).
H. Iio, H. Nagaoka, and Y. Kishi, J. Am. Chem. Soc.,102, 7963 (1980).
H. Nagaoka et al., J. Am. Chem. Soc.,102, 7965 (1980).
M. DeRosa, A. Gambacorts, and L. Minale, J. Chem. Soc., Chem. Commun., 392 (1975).
A. C. Neish, in: The Biochemistry of Phenolic Compounds [Russian translation], Moscow (1968), p. 234.
F. Schönhofer, Hoppe-Seyler's Z. Physiol. Chem.,274, 1 (1942).
E. S. Josephson et al., J. Pharmacol. Exp. Ther.,103, 7 (1951).
N. L. Drake and Y. T. Pratt, J. Am. Chem. Soc.,73, 544 (1951).
F. J. Bullock et al., J. Med. Chem.,13, 97 (1970).
F. J. Bullock and J. F. Tweede, J. Med. Chem., 261 (1970).
D. C. Warhurst, in: Chemotherapeutic Agents in the Study of Parasites, London (1973), pp. 4–8.
P. Nickel and E. Fink, Justus Liebigs Ann. Chem.,749, 367 (1976).
C. W. Schellhammer et al., Naturwissenschaften,46, 82 (1956).
P. Nickel and W. Steuding, Arch. Pharm. (Weinheim),312, 971 (1979).
C. W. Schellhammer and S. Petersen, Justus Liebigs Ann. Chem.,624, 108 (1959).
C. W. Schellhammer, West German Patent No. 1115253; Chem. Abstr.,56, 4740d (1962).
C. W. Schellhammer, S. Petersen, and G. Domagk, West German Patent No. 1102161; Chem. Abstr.,57, 836a (1962).
C. W. Schellhammer, West German Patent No. 1108699; Chem. Abstr.,56, 8730f (1962).
T. H. Porter and K. Fokers, Angew. Chem., Int. Ed.,13, 559 (1974).
R. A. Heacock, Adv. Heterocycl. Chem.,5, 205 (1965).
A. Hoffer, in: Enzymes in Mental Health, Toronto (1966), p. 43.
V. O. Osinskaya, in: Adrenaline and Noradrenaline [in Russian], Moscow (1964), p. 118.
J. Axelrod, in: Enzymes in Mental Health, Toronto (1966), p. 152.
W. C. Vander and J. C. Johnson, Biochem. Pharmacol.,19, 2001 (1970).
Z. L. Hegedus and M. D. Altschule, Arch. Int. Pharmacodyn.,186, 48 (1970).
Kirk-Othmer Encyclopedia of Chemical Technology, 3rd edn., Vol. 4, New York (1978), P. 13.
K. Fujima, H. Kato, and H. Uda, Japanese Patent No. 52-85739; Ref. Zh. Khim., No. 50151P (1979).
J. S. Driscoll, Cancer Chemother. Rep., Part 2,4, l (1974).
I. D. Entwistle, P. J. Williams, and B. R. J. Devlin, West German Patent No. 2107053; Chem. Abstr.,76, 3854m (1972).
C. W. Schellhammer, S. Petersen, and G. Domagk, West German Patent No. 1102161; Chem. Abstr.,57, 836a (1962).
H. Kano, M. Ogata, and H. Yukinaga, Angew. Chem., Int. Ed.,13, 212 (1974).
M. V. Rubtsov and A. G. Baichikov, Syntheses of Medicinal Preparations [in Russian], Moscow (1970).
R. F. Silver and H. L. Holmes, Can J. Chem.,46, 1859 (1968).
Y. C. Martin, T. M. Bustadt, and K. R. Lynn, J. Med. Chem.,16, 1089 (1973).
M. Negwer, Organisch-chemische Arzneimittel und ihre Synonyma, Vol. 1, Berlin (1978), No. 2816, p. 505.
Ibid., No. 3118, p. 566.
Ibid., Vol. 2, No. 5377, p. 1001.
Ibid. Vol. 1, No. 1286-01, p. 233.
Ibid., Vol. 1, No. 1795, p. 325.
Author information
Authors and Affiliations
Additional information
Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 16, No. 6, pp. 667–678, June, 1982.
Rights and permissions
About this article
Cite this article
Tsizin, Y.S., Chernyak, S.A. Biologically active heterocyclic quinones (review). Pharm Chem J 16, 435–445 (1982). https://doi.org/10.1007/BF00759748
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00759748