메뉴 건너뛰기




Volumn 30, Issue 10, 1987, Pages 1918-1928

Streptonigrin and Lavendamycin Partial Structures. Probes for the Minimum, Potent Pharmacophore of Streptonigrin, Lavendamycin, and Synthetic Quinoline-5,8-diones

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 3 (7 AMINO 5,8 DIOXO 2 QUINOLYL)BENZOIC ACID; 6 (7 AMINO 5,8 DIOXO 2 QUINOLYL)PICOLINIC ACID; LAVENDAMYCIN; RUFOCROMOMYCIN; STREPTONIGRIN METHYL ESTER; UNCLASSIFIED DRUG;

EID: 0000302152     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00393a040     Document Type: Article
Times cited : (133)

References (68)
  • 1
    • 0345966760 scopus 로고
    • Identical with bruneomycin (Actinomyces albus var. bruneomycini). Kudrina, E. S.; Olkhovatova, O. L.; Murav'eva, L. I.; Gauze, G. F. Antibiotiki (Moscow) 1966,11, 400. Brazhnikova, M. G.; Ponomarenko, V. I.; Kovsharova, I. N.; Kruglyak, E. B.; Proshlyakova, V. V. Antibiotiki (Moscow) 1968,13, 99. Identical with rufochromomycin (Streptomyces rufochromogenus). Chem. Abstr. 1961, 55, 25158.
    • Streptonigrin isolation: Rao, K. V.; Cullen, W. P. Antibiot. Annu. 1959, 950. Identical with bruneomycin (Actinomyces albus var. bruneomycini). Kudrina, E. S.; Olkhovatova, O. L.; Murav'eva, L. I.; Gauze, G. F. Antibiotiki (Moscow) 1966,11, 400. Brazhnikova, M. G.; Ponomarenko, V. I.; Kovsharova, I. N.; Kruglyak, E. B.; Proshlyakova, V. V. Antibiotiki (Moscow) 1968,13, 99. Identical with rufochromomycin (Streptomyces rufochromogenus). Chem. Abstr. 1961, 55, 25158.
    • (1959) Antibiot. Annu. , pp. 950
    • Rao, K.V.1    Cullen, W.P.2
  • 2
    • 0345966760 scopus 로고
    • Identical with bruneomycin (Actinomyces albus var. bruneomycini). Kudrina, E. S.; Olkhovatova, O. L.; Murav'eva, L. I.; Gauze, G. F. Antibiotiki (Moscow) 1966,11, 400. Brazhnikova, M. G.; Ponomarenko, V. I.; Kovsharova, I. N.; Kruglyak, E. B.; Proshlyakova, V. V. Antibiotiki (Moscow) 1968,13, 99. Identical with rufochromomycin (Streptomyces rufochromogenus). Chem. Abstr. 1961, 55, 25158.
    • Streptonigrin isolation: Rao, K. V.; Cullen, W. P. Antibiot. Annu. 1959, 950. Identical with bruneomycin (Actinomyces albus var. bruneomycini). Kudrina, E. S.; Olkhovatova, O. L.; Murav'eva, L. I.; Gauze, G. F. Antibiotiki (Moscow) 1966,11, 400. Brazhnikova, M. G.; Ponomarenko, V. I.; Kovsharova, I. N.; Kruglyak, E. B.; Proshlyakova, V. V. Antibiotiki (Moscow) 1968,13, 99. Identical with rufochromomycin (Streptomyces rufochromogenus). Chem. Abstr. 1961, 55, 25158.
    • (1959) Antibiot. Annu. , pp. 950
    • Cullen, W.P.1
  • 4
    • 0016688859 scopus 로고
    • Streptonigrin single-crystal X-ray structure determination
    • Streptonigrin single-crystal X-ray structure determination: Chiu, Y.-Y.H.; Lipscomb, W. N. J. Am. Chem. Soc. 1975, 97, 2525.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 2525
    • Chiu, Y.-Y.H.1
  • 5
    • 0343751868 scopus 로고
    • Streptonigrin atropisomers
    • Streptonigrin atropisomers: Dholakia, S.; Gillard, R. D. Tetrahedron 1981, 37, 2929.
    • (1981) Tetrahedron , vol.37 , pp. 2929
    • Dholakia, S.1    Gillard, R.2
  • 6
    • 0020053088 scopus 로고
    • Streptonigrin total syntheses: Kende, A. S.; Lorah, D. P.; Boatman, R. J. J. Am. Chem. Soc. 1981, 103, 1271. Boger, D. L.; Panek, J. S. J. Am. Chem. Soc. 1985,107, 5746; J. Org. Chem. 1983, 48, 621.
    • Streptonigrin total syntheses: Weinreb, S. M.; Basha, F. Z.; Hibino, S.; Khatri, N. A.; Kim, D.; Pye, W. E.; Wu, T.-T. J. Am. Chem. Soc. 1982,104, 536. Kende, A. S.; Lorah, D. P.; Boatman, R. J. J. Am. Chem. Soc. 1981, 103, 1271. Boger, D. L.; Panek, J. S. J. Am. Chem. Soc. 1985,107, 5746; J. Org. Chem. 1983, 48, 621.
    • (1982) Am. Chem. Soc. , vol.104 , pp. 536
    • Weinreb, S.M.1    Basha, F.Z.2
  • 9
    • 85022641967 scopus 로고
    • In Bioorganic Chemistry; Van Tamelen, E. E.
    • Lown, J. W. In Bioorganic Chemistry; Van Tamelen, E. E., Ed.; Academic: New York, 1977; pp 95-121.
    • (1977) Academic: New York , pp. 95-121
    • Lown, J.W.1
  • 10
    • 85022725616 scopus 로고
    • Metal Ions in Biological Systems
    • Hajdu, J. Metal Ions in Biological Systems; Marcel Dekker: New York, 1985; Vol. 19, Chapter 3.
    • (1985) Marcel Dekker: New York , vol.19 , pp. 3
    • Hajdu, J.1
  • 11
    • 85022691665 scopus 로고
    • Bhuyan, B. K. In Antibiotics I. Mechanism of Action; Gottlieb, I. D., Shaw, P. D., Eds.; Springer-Verlag: New York, 1967; pp 173-180.
    • (1967) Springer-Verlag: New York , pp. 173-180
    • Bhuyan, B.K.1
  • 22
    • 0017652875 scopus 로고
    • Forcier, R. J.; McIntyre, O. R.; Nissen, N. I.; Pajak, T. F.; Glidewell, O.; Holland, J. F. Med. Pediatr. Oncol. 1978, 4, 351.
    • Nissen, N. L.; Pajak, T.; Glidewell, O.; Blom, H.; Flaherty, M.; Hayes, D.; McIntyre, R.; Holland, J. F. Cancer Treat. Rep. 1977, 61, 1097. Forcier, R. J.; McIntyre, O. R.; Nissen, N. I.; Pajak, T. F.; Glidewell, O.; Holland, J. F. Med. Pediatr. Oncol. 1978, 4, 351.
    • (1977) Cancer Treat. Rep. , vol.61 , pp. 1097
    • Nissen, N.L.1    Pajak, T.2    Glidewell, O.3
  • 25
    • 0019974608 scopus 로고
    • Lavendamycin isolation and antimicrobial and antitumor testing
    • Lavendamycin isolation and antimicrobial and antitumor testing: Balitz, D. M.; Bush, J. A.; Bradner, W. T.; Doyle, T. W.; O'Herron, F. A.; Nettleton, D. E. J. Antibiot. 1982, 35, 259.
    • (1982) J. Antibiot. , vol.35 , pp. 259
    • Balitz, D.M.1    Bush, J.A.2    Bradner, W.3
  • 26
    • 0019813081 scopus 로고
    • Lavendamycin structure determination
    • Lavendamycin structure determination: Doyle, T. W.; Balitz, D. M.; Grulich, R. E.; Nettleton, D. E.; Gould, S. J.; Tann, C.-h.; Moews, A. E. Tetrahedron Lett. 1981, 22, 4595.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 4595
    • Doyle, T.W.1    Balitz, D.M.2    Grulich, R.E.3
  • 27
    • 0023142678 scopus 로고
    • Lavendamycin biosynthesis
    • Lavendamycin biosynthesis: Erickson, W. R.; Gould, S. J. J. Am. Chem. Soc. 1985, 107, 5831. Erickson, W. R.; Gould, S. J. J. Am. Chem. Soc. 1987, 109, 620.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 620
    • Erickson, W.R.1    Gould, S.2
  • 28
    • 0021338389 scopus 로고
    • Lavendamycin total syntheses: Hibino, S.; Okazaki, M.; Ichikawa, M.; Sato, K.; Ishizu, T. Heterocycles 1985, 23, 261. Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5790. Rao, A. V. R.; Chavan, S. P.; Sivadasan, L. Tetrahedron 1986, 42, 5065.
    • Lavendamycin total syntheses: Kende, A. S.; Ebetino, F. H. Tetrahedron Lett. 1984, 25, 923. Hibino, S.; Okazaki, M.; Ichikawa, M.; Sato, K.; Ishizu, T. Heterocycles 1985, 23, 261. Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5790. Rao, A. V. R.; Chavan, S. P.; Sivadasan, L. Tetrahedron 1986, 42, 5065.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 923
    • Kende, A.S.1    Ebetino, F.H.2
  • 29
    • 0018741206 scopus 로고
    • Bachur, N. R.; Gordon, S. L.; Gee, V. Cancer Res. 1978, 38, 1745. Bachur, N. R.; Gordon, S. L.; Gee, V.; Kon, H. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 954.
    • (1979) Proc. Natl. Acad. Sci. , vol.76 , pp. 954
    • Bachur, N.R.1    Gordon, S.L.2
  • 30
    • 0017238917 scopus 로고
    • No evidence was found for streptonigrin-DNA interaction in the presence or absence of Cu(II).
    • Cone, R.; Hasan, S. K.; Lown, J. W.; Morgan, A. R. Can. J. Biochem. 1976, 54, 219. No evidence was found for streptonigrin-DNA interaction in the presence or absence of Cu(II).
    • (1976) Can. J. Biochem. , vol.54 , pp. 219
    • Cone, R.1    Hasan, S.K.2    Lown, J.W.3    Morgan, A.R.4
  • 42
    • 0013936369 scopus 로고
    • Streptonigrin methyl ester
    • Streptonigrin methyl ester: Kremer, W. B.; Laszlo, J. Biochem. Pharmacol. 1966, 15, 1111. See also ref 7-13.
    • (1966) Biochem. Pharmacol. , vol.15 , pp. 1111
    • Kremer, W.B.1    Laszlo, J.2
  • 43
    • 0022412203 scopus 로고
    • Streptonigrin hydrazide, streptonigrin amide(s), streptonigrin methyl ester
    • Streptonigrin hydrazide, streptonigrin amide(s), streptonigrin methyl ester: Inouye, Y.; Oleada, H.; Roy, S. K.; Miyasaka, T.; Hibino, S.; Tanaka, N.; Nakamura, S. J. Antibiot. 1985, 38, 1429.
    • (1985) J. Antibiot. , vol.38 , pp. 1429
    • Inouye, Y.1    Oleada, H.2    Roy, S.K.3    Miyasaka, T.4
  • 47
    • 0017172379 scopus 로고
    • Angew. Chem., Int. Ed. Engl. 1967, 6, 82.
    • Streptonigrin AB ring system: Liao, T. K.; Nyberg, W. H.; Cheng, C. C. J. Heterocycl. Chem. 1976, 13, 1063. Angew. Chem., Int. Ed. Engl. 1967, 6, 82.
    • (1976) J. Heterocycl. Chem. , vol.13 , pp. 1063
    • Liao, T.K.1    Nyberg, W.H.2    Cheng, C.C.3
  • 48
    • 2142775176 scopus 로고
    • Streptonigrin and lavendamycin AB and ABC ring systems
    • Streptonigrin and lavendamycin AB and ABC ring systems: Boger, D. L.; Yasuda, M. Heterocycles 1986, 24, 1067.
    • (1986) Heterocycles , vol.24 , pp. 1067
    • Boger, D.L.1    Yasuda, M.2
  • 50
    • 0000306108 scopus 로고
    • Lavendamycin AB, ABC, and CDE γ-carboline ring systems: Boger, D. L.; Panek, J. S. Tetrahedron Lett. 1984, 25, 3175.
    • Lavendamycin AB, ABC, and CDE γ-carboline ring systems: Boger, D. L.; Duff, S. R.; Panek, J. S.; Yasuda, M. J. Org. Chem. 1985, 50, 5782. Boger, D. L.; Panek, J. S. Tetrahedron Lett. 1984, 25, 3175.
    • (1985) J. Org. Chem. , vol.50 , pp. 5782
    • Boger, D.L.1    Duff, S.R.2    Panek, J.S.3    Yasuda, M.4
  • 51
    • 0021019048 scopus 로고
    • Renault, J.; Giorgi-Renault, S.; Mailliet, P.; Baron, M.; Paoletti, C.; Cros, S. Eur. J. Med. Chem.—Chim. Ther. 1981, 16, 24; 1981, 16, 545; 1983, 18, 134.
    • Renault, J.; Giorgi-Renault, S.; Baron, M.; Mailliet, P.; Paoletti, C.; Cros, S.; Viosin, E. J. Med. Chem. 1983, 26, 1715. Renault, J.; Giorgi-Renault, S.; Mailliet, P.; Baron, M.; Paoletti, C.; Cros, S. Eur. J. Med. Chem.—Chim. Ther. 1981, 16, 24; 1981, 16, 545; 1983, 18, 134.
    • (1983) J. Med. Chem. , vol.26 , pp. 1715
    • Renault, J.1    Giorgi-Renault, S.2    Baron, M.3
  • 52
    • 0020679301 scopus 로고
    • references cited therein. Albert, A. Selective Toxicity, 4th ed.; Chapman and Hall: London, England, 1973.
    • Hodnett, E. M.; Wongwiechintana, C.; Dunn, W. J., Ill; Marrs, P. J. Med. Chem. 1983, 26, 570 and references cited therein. Albert, A. Selective Toxicity, 4th ed.; Chapman and Hall: London, England, 1973.
    • (1983) J. Med. Chem. , vol.26 , pp. 570
    • Hodnett, E.M.1    Wongwiechintana, C.2    Dunn, W.J.3
  • 57
    • 0003151465 scopus 로고
    • Cheng, C. C.; Van, S. J. Org. React. (N.Y.) 1982, 28, 37.
    • (1982) Org. React. , vol.28 , pp. 37
    • Cheng, C.C.1
  • 60
    • 0021338389 scopus 로고
    • Kende, A. S.; Ebetino, F. H.; Battista, R.; Lorah, D. P.; Lodge, E. Heterocycles 1984, 21, 91.
    • Kende, A. S.; Ebetino, F. H. Tetrahedron Lett. 1984, 25, 923. Kende, A. S.; Ebetino, F. H.; Battista, R.; Lorah, D. P.; Lodge, E. Heterocycles 1984, 21, 91.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 923
    • Kende, A.S.1    Ebetino, F.H.2
  • 63
    • 0000433217 scopus 로고
    • Meyers, A. L; Durandetta, J. L.; Marava, R. J. Org. Chem. 1975, 40, 2025.
    • Corey, E. J.; Chaykovsky, M. J. J. Am. Chem. Soc. 1965, 87, 1345. Meyers, A. L; Durandetta, J. L.; Marava, R. J. Org. Chem. 1975, 40, 2025.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 1345
    • Corey, E.J.1    Chaykovsky, M.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.