메뉴 건너뛰기




Volumn 45, Issue 1, 1997, Pages 125-133

Synthesis and biological evaluation of novel cyclic enediyne compounds related to dynemicin A as antitumor agents

Author keywords

antitumor activity; bicyclo 7,3,1 tridee 4 ene 2,6 diyne; cyclic enediyne; cytotoxicity; DNA cleavage

Indexed keywords

ANTINEOPLASTIC AGENT; DYNEMICIN A; DYNEMICIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031030379     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.125     Document Type: Article
Times cited : (14)

References (57)
  • 1
    • 0026045597 scopus 로고
    • For reviews, see: a) Nicolaou K. C., Dai W.-M., Angew. Chem. Int. Ed. Engl., 30, 1387-1416 (1991); b) Nicolaou K. C., Smith A. L., Yue E. W., Proc. Natl. Acad. Sci. U.S.A., 90, 5881-5888 (1993); c) Grissom J. W., Gunawardena G. U., Klingberg D., Huang D., Tetrahedron, 52, 6453-6518 (1996); d) Skrydstrup T., Ulibarri G., Audrain H., Grierson D. S., "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed. by Lukacs G., Springer-Verlag, Berlin, 1993, pp. 213-291.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1387-1416
    • Nicolaou, K.C.1    Dai, W.-M.2
  • 2
    • 0027319406 scopus 로고
    • For reviews, see: a) Nicolaou K. C., Dai W.-M., Angew. Chem. Int. Ed. Engl., 30, 1387-1416 (1991); b) Nicolaou K. C., Smith A. L., Yue E. W., Proc. Natl. Acad. Sci. U.S.A., 90, 5881-5888 (1993); c) Grissom J. W., Gunawardena G. U., Klingberg D., Huang D., Tetrahedron, 52, 6453-6518 (1996); d) Skrydstrup T., Ulibarri G., Audrain H., Grierson D. S., "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed. by Lukacs G., Springer-Verlag, Berlin, 1993, pp. 213-291.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 5881-5888
    • Nicolaou, K.C.1    Smith, A.L.2    Yue, E.W.3
  • 3
    • 0030005845 scopus 로고    scopus 로고
    • For reviews, see: a) Nicolaou K. C., Dai W.-M., Angew. Chem. Int. Ed. Engl., 30, 1387-1416 (1991); b) Nicolaou K. C., Smith A. L., Yue E. W., Proc. Natl. Acad. Sci. U.S.A., 90, 5881-5888 (1993); c) Grissom J. W., Gunawardena G. U., Klingberg D., Huang D., Tetrahedron, 52, 6453-6518 (1996); d) Skrydstrup T., Ulibarri G., Audrain H., Grierson D. S., "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed. by Lukacs G., Springer-Verlag, Berlin, 1993, pp. 213-291.
    • (1996) Tetrahedron , vol.52 , pp. 6453-6518
    • Grissom, J.W.1    Gunawardena, G.U.2    Klingberg, D.3    Huang, D.4
  • 4
    • 0026045597 scopus 로고
    • ed. by Lukacs G., Springer-Verlag, Berlin
    • For reviews, see: a) Nicolaou K. C., Dai W.-M., Angew. Chem. Int. Ed. Engl., 30, 1387-1416 (1991); b) Nicolaou K. C., Smith A. L., Yue E. W., Proc. Natl. Acad. Sci. U.S.A., 90, 5881-5888 (1993); c) Grissom J. W., Gunawardena G. U., Klingberg D., Huang D., Tetrahedron, 52, 6453-6518 (1996); d) Skrydstrup T., Ulibarri G., Audrain H., Grierson D. S., "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products," ed. by Lukacs G., Springer-Verlag, Berlin, 1993, pp. 213-291.
    • (1993) Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products , pp. 213-291
    • Skrydstrup, T.1    Ulibarri, G.2    Audrain, H.3    Grierson, D.S.4
  • 11
    • 0026350496 scopus 로고
    • Konishi M., Ohkuma H., Matsumoto K., Kamei T., Miyaki T., Oki T., Kawaguchi H., VanDuyne G. D., Clardy J., J. Antibiot., 42, 1449-1452 (1989); Kamei H., Nishiyama Y., Takahashi A., Obi Y., Oki T., ibid., 44, 1306-1311 (1991); Konishi M., Ohkuma H., Tsuno T., Oki T., VanDuyne G. D., Clardy J., J. Am. Chem. Soc., 112, 3715-3716 (1990).
    • (1991) J. Antibiot. , vol.44 , pp. 1306-1311
    • Kamei, H.1    Nishiyama, Y.2    Takahashi, A.3    Obi, Y.4    Oki, T.5
  • 12
    • 0025100205 scopus 로고
    • Konishi M., Ohkuma H., Matsumoto K., Kamei T., Miyaki T., Oki T., Kawaguchi H., VanDuyne G. D., Clardy J., J. Antibiot., 42, 1449-1452 (1989); Kamei H., Nishiyama Y., Takahashi A., Obi Y., Oki T., ibid., 44, 1306-1311 (1991); Konishi M., Ohkuma H., Tsuno T., Oki T., VanDuyne G. D., Clardy J., J. Am. Chem. Soc., 112, 3715-3716 (1990).
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 3715-3716
    • Konishi, M.1    Ohkuma, H.2    Tsuno, T.3    Oki, T.4    Vanduyne, G.D.5    Clardy, J.6
  • 17
    • 0025264829 scopus 로고
    • For recent studies on the action mechanism, see: Semmelhack M. F., Gallagher J., Cohen D., Tetrahedron Lett., 31, 1521-1522 (1990); Sugiura Y., Shiraki T., Konishi M., Oki T., Proc. Natl. Acad. Sci. U.S.A., 87, 3831-3835 (1990); Snyder J. P., Tipsword G. E., J. Am. Chem. Soc., 112, 4040-4042 (1990); Kusakabe T., Maekawa K., Ichikawa A., Uesugi M., Sugiura Y., Biochem., 32, 11669-11675 (1993).
    • (1990) Tetrahedron Lett. , vol.31 , pp. 1521-1522
    • Semmelhack, M.F.1    Gallagher, J.2    Cohen, D.3
  • 18
    • 0025368037 scopus 로고
    • For recent studies on the action mechanism, see: Semmelhack M. F., Gallagher J., Cohen D., Tetrahedron Lett., 31, 1521-1522 (1990); Sugiura Y., Shiraki T., Konishi M., Oki T., Proc. Natl. Acad. Sci. U.S.A., 87, 3831-3835 (1990); Snyder J. P., Tipsword G. E., J. Am. Chem. Soc., 112, 4040-4042 (1990); Kusakabe T., Maekawa K., Ichikawa A., Uesugi M., Sugiura Y., Biochem., 32, 11669-11675 (1993).
    • (1990) Proc. Natl. Acad. Sci. U.S.A. , vol.87 , pp. 3831-3835
    • Sugiura, Y.1    Shiraki, T.2    Konishi, M.3    Oki, T.4
  • 19
    • 0000892836 scopus 로고
    • For recent studies on the action mechanism, see: Semmelhack M. F., Gallagher J., Cohen D., Tetrahedron Lett., 31, 1521-1522 (1990); Sugiura Y., Shiraki T., Konishi M., Oki T., Proc. Natl. Acad. Sci. U.S.A., 87, 3831-3835 (1990); Snyder J. P., Tipsword G. E., J. Am. Chem. Soc., 112, 4040-4042 (1990); Kusakabe T., Maekawa K., Ichikawa A., Uesugi M., Sugiura Y., Biochem., 32, 11669-11675 (1993).
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4040-4042
    • Snyder, J.P.1    Tipsword, G.E.2
  • 20
    • 0027442672 scopus 로고
    • For recent studies on the action mechanism, see: Semmelhack M. F., Gallagher J., Cohen D., Tetrahedron Lett., 31, 1521-1522 (1990); Sugiura Y., Shiraki T., Konishi M., Oki T., Proc. Natl. Acad. Sci. U.S.A., 87, 3831-3835 (1990); Snyder J. P., Tipsword G. E., J. Am. Chem. Soc., 112, 4040-4042 (1990); Kusakabe T., Maekawa K., Ichikawa A., Uesugi M., Sugiura Y., Biochem., 32, 11669-11675 (1993).
    • (1993) Biochem. , vol.32 , pp. 11669-11675
    • Kusakabe, T.1    Maekawa, K.2    Ichikawa, A.3    Uesugi, M.4    Sugiura, Y.5
  • 21
    • 33947088453 scopus 로고
    • Jones R. R., Bergman R. G., J. Am. Chem. Soc., 94, 660-661 (1972); Lockhart T. P., Gomita P. B., Bergman R. G., ibid., 103, 4091-4096 (1981); Darby N., Kim C. U., Salaun J. A., Shelton K. W., Takada S., Masamune S., J. Chem. Soc., Chem. Commun., 1971, 1516-1517.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 660-661
    • Jones, R.R.1    Bergman, R.G.2
  • 22
    • 33845557570 scopus 로고
    • Jones R. R., Bergman R. G., J. Am. Chem. Soc., 94, 660-661 (1972); Lockhart T. P., Gomita P. B., Bergman R. G., ibid., 103, 4091-4096 (1981); Darby N., Kim C. U., Salaun J. A., Shelton K. W., Takada S., Masamune S., J. Chem. Soc., Chem. Commun., 1971, 1516-1517.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 4091-4096
    • Lockhart, T.P.1    Gomita, P.B.2    Bergman, R.G.3
  • 28
    • 85049949910 scopus 로고    scopus 로고
    • For review, see: Maier M. E., Synlett. 1995, 13-26.
    • Synlett. , vol.1995 , pp. 13-26
    • Maier, M.E.1
  • 36
    • 0027520529 scopus 로고    scopus 로고
    • Wender P. A., Zercher C. K., Beckham S., Haubold E., J. Org. Chem., 58, 5867-5869 (1993); Wender P. A., Zercher C. K., J. Am. Chem. Soc., 113, 2311-2313 (1991); Wender P. A., Beckham S., O'Leary J. G., Synthesis, 1994, 1278-1282.
    • (1993) J. Org. Chem. , vol.58 , pp. 5867-5869
    • Wender, P.A.1    Zercher, C.K.2    Beckham, S.3    Haubold, E.4
  • 37
    • 0025851885 scopus 로고
    • Wender P. A., Zercher C. K., Beckham S., Haubold E., J. Org. Chem., 58, 5867-5869 (1993); Wender P. A., Zercher C. K., J. Am. Chem. Soc., 113, 2311-2313 (1991); Wender P. A., Beckham S., O'Leary J. G., Synthesis, 1994, 1278-1282.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2311-2313
    • Wender, P.A.1    Zercher, C.K.2
  • 38
    • 0027520529 scopus 로고    scopus 로고
    • Wender P. A., Zercher C. K., Beckham S., Haubold E., J. Org. Chem., 58, 5867-5869 (1993); Wender P. A., Zercher C. K., J. Am. Chem. Soc., 113, 2311-2313 (1991); Wender P. A., Beckham S., O'Leary J. G., Synthesis, 1994, 1278-1282.
    • Synthesis , vol.1994 , pp. 1278-1282
    • Wender, P.A.1    Beckham, S.2    O'Leary, J.G.3
  • 51
    • 0040988663 scopus 로고
    • Narang S. A., Bhanot O. S., Goodchild J., Wightman R. J., Dheer S. K., J. Am. Chem. Soc., 94, 6183-6189 (1972); Isobe M., Kitamura M., Goto T., ibid., 104, 4997-4999 (1982); Isobe M., Ichikawa Y., Goto T., Tetrahedron Lett., 26, 5199-5202 (1985).
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4997-4999
    • Isobe, M.1    Kitamura, M.2    Goto, T.3
  • 52
    • 0021851643 scopus 로고
    • Narang S. A., Bhanot O. S., Goodchild J., Wightman R. J., Dheer S. K., J. Am. Chem. Soc., 94, 6183-6189 (1972); Isobe M., Kitamura M., Goto T., ibid., 104, 4997-4999 (1982); Isobe M., Ichikawa Y., Goto T., Tetrahedron Lett., 26, 5199-5202 (1985).
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5199-5202
    • Isobe, M.1    Ichikawa, Y.2    Goto, T.3
  • 54
    • 0342502260 scopus 로고    scopus 로고
    • For similar enediynes containing an anthraquinone unit as an intercalating moiety, see ref. 1a
    • For similar enediynes containing an anthraquinone unit as an intercalating moiety, see ref. 1a.
  • 56
    • 0343807528 scopus 로고    scopus 로고
    • For the DNA cleavage studies of the other analogs of dynemicin A, see refs. 17 and 18
    • For the DNA cleavage studies of the other analogs of dynemicin A, see refs. 17 and 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.