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Volumn 50, Issue 19, 2007, Pages 4561-4571

Synthesis and biological evaluation of imidazoquinoxalinones, imidazole analogues of pyrroloiminoquinone marine natural products

Author keywords

[No Author keywords available]

Indexed keywords

8 [2 (1H INDOL 3' YL)ETHYLAMINO]4,5 DIHYDROIMIDAZO[1,5,4 DE]QUINOXALIN 9 ONE; 8 [2 (4' HYDROXYPHENYL)ETHYLAMINO]4,5 DIHYDROIMIDAZO[1,5,4 DE]QUINOXALIN 9 ONE; AMIDINE; BENZIMIDAZOLE DERIVATIVE; ETHYLENE; ETOPOSIDE; IMIDAZOLE DERIVATIVE; INDOLE; PYRROLOIMINOQUINONE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34648830279     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0700870     Document Type: Article
Times cited : (23)

References (35)
  • 1
    • 0025762137 scopus 로고    scopus 로고
    • Copp, B. R.; Ireland, C. M.; Barrows, L. R. Wakayin: A novel cytotoxic pyrroloiminoquinone alkaloid from the ascidian Clavelina species. J. Org. Chem. 1991, 56 (15), 4596-4597.
    • Copp, B. R.; Ireland, C. M.; Barrows, L. R. Wakayin: A novel cytotoxic pyrroloiminoquinone alkaloid from the ascidian Clavelina species. J. Org. Chem. 1991, 56 (15), 4596-4597.
  • 2
    • 0027260378 scopus 로고    scopus 로고
    • Carney, J. R.; Scheuer, P. J.; Keliy-Borges, M. Makaluvamine G, a cytotoxic pigment from an Indonesian sponge Histodermella sp. Tetrahedron 1993, 49, 8483-8486.
    • Carney, J. R.; Scheuer, P. J.; Keliy-Borges, M. Makaluvamine G, a cytotoxic pigment from an Indonesian sponge Histodermella sp. Tetrahedron 1993, 49, 8483-8486.
  • 3
    • 0027167775 scopus 로고
    • Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya
    • Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. Novel cytotoxic topoisomerase II inhibiting pyrroloiminoquinones from Fijian sponges of the genus Zyzzya. J. Am. Chem. Soc. 1993, 115, 1632-1638.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 1632-1638
    • Radisky, D.C.1    Radisky, E.S.2    Barrows, L.R.3    Copp, B.R.4    Kramer, R.A.5    Ireland, C.M.6
  • 4
    • 0029585977 scopus 로고    scopus 로고
    • Schmidt, E. W.; Harper, M. K.; Faulkner, D. J. Makaluvamines H-M and damirone C from the Pohnpeian sponge Zyzzya fuliginosa. J. Nat. Prod. 1995, 58 (12), 1861-1867.
    • Schmidt, E. W.; Harper, M. K.; Faulkner, D. J. Makaluvamines H-M and damirone C from the Pohnpeian sponge Zyzzya fuliginosa. J. Nat. Prod. 1995, 58 (12), 1861-1867.
  • 5
    • 0029905334 scopus 로고    scopus 로고
    • Epinardins A-D, new pyrroloiminoquinone alkaloids of undetermined deep-water green demosponges from pre-Antarctic Indian Ocean
    • D'Ambrosio, M.; Guerriero, A.; Chiasera, G.; Pietra, F. Epinardins A-D, new pyrroloiminoquinone alkaloids of undetermined deep-water green demosponges from pre-Antarctic Indian Ocean. Tetrahedron 1996, 52 (26), 8899-8906.
    • (1996) Tetrahedron , vol.52 , Issue.26 , pp. 8899-8906
    • D'Ambrosio, M.1    Guerriero, A.2    Chiasera, G.3    Pietra, F.4
  • 7
    • 0031000076 scopus 로고    scopus 로고
    • Venables, D. A.; Concepcion, G. P.; Matsumoto, S. S.; Barrows, L. R.; Ireland, C. M. Makaluvamine N: A new pyrroloiminoquinone from Zyzzya fuliginosa. J. Nat. Prod. 1997, 60 (4), 408-410.
    • Venables, D. A.; Concepcion, G. P.; Matsumoto, S. S.; Barrows, L. R.; Ireland, C. M. Makaluvamine N: A new pyrroloiminoquinone from Zyzzya fuliginosa. J. Nat. Prod. 1997, 60 (4), 408-410.
  • 9
    • 0034752653 scopus 로고    scopus 로고
    • Casapullo, A.; Cutignano, A.; Bruno, I.; Bifulco, G.; Debitus, C.; GomezPaloma, L.; Riccio, R. Makaluvamine P, a new cytotoxic pyrroloiminoquinone from Zyzzya cf. fuliginosa. J. Nat. Prod. 2001, 64 (10), 1354-1356.
    • Casapullo, A.; Cutignano, A.; Bruno, I.; Bifulco, G.; Debitus, C.; GomezPaloma, L.; Riccio, R. Makaluvamine P, a new cytotoxic pyrroloiminoquinone from Zyzzya cf. fuliginosa. J. Nat. Prod. 2001, 64 (10), 1354-1356.
  • 11
    • 0025313288 scopus 로고
    • Synthesis and physical studies of azamitosene and iminoazamitosene reductive alkylating agents. Iminoquinone hydrolytic stability, syn/anti isomerization, and electrochemistry
    • Islam, I.; Skibo, E. B. Synthesis and physical studies of azamitosene and iminoazamitosene reductive alkylating agents. Iminoquinone hydrolytic stability, syn/anti isomerization, and electrochemistry. J. Org. Chem. 1990, 55, 3195-3205.
    • (1990) J. Org. Chem , vol.55 , pp. 3195-3205
    • Islam, I.1    Skibo, E.B.2
  • 12
    • 0029013409 scopus 로고
    • Pyrrolo[1 ,2-a] benzimidazole-based quinones and iminoquinones. The role of the 3-substituent on cytotoxicity
    • Schulz, W. G.; Islam, E.; Skibo, E. B. Pyrrolo[1 ,2-a] benzimidazole-based quinones and iminoquinones. The role of the 3-substituent on cytotoxicity. J. Med. Chem. 1995, 38, 109-118.
    • (1995) J. Med. Chem , vol.38 , pp. 109-118
    • Schulz, W.G.1    Islam, E.2    Skibo, E.B.3
  • 13
    • 1542530183 scopus 로고    scopus 로고
    • The organic chemistry of the pyrroio[1,2-a]benzimidazole anti-tumor agents. An example of rational drug design
    • Skibo, E. B.; Islam, I.; Schulz, W. G.; Zhou, R.; Bess, L.; Boruah, R. The organic chemistry of the pyrroio[1,2-a]benzimidazole anti-tumor agents. An example of rational drug design. Synlett 1996, 297-309.
    • (1996) Synlett , pp. 297-309
    • Skibo, E.B.1    Islam, I.2    Schulz, W.G.3    Zhou, R.4    Bess, L.5    Boruah, R.6
  • 14
    • 0030968873 scopus 로고    scopus 로고
    • Studies of pyrroio[1,2-a]benzimidazole quinone DT-diaphorase substrate activity, topoisomerase II inhibition activity, and DNA reductive aikylation
    • Skibo, E. S.; Gordon, S.; Bess, L.; Boruah, R.; Heileman, J. Studies of pyrroio[1,2-a]benzimidazole quinone DT-diaphorase substrate activity, topoisomerase II inhibition activity, and DNA reductive aikylation. J. Med. Chem. 1997, 40, 1327-1339.
    • (1997) J. Med. Chem , vol.40 , pp. 1327-1339
    • Skibo, E.S.1    Gordon, S.2    Bess, L.3    Boruah, R.4    Heileman, J.5
  • 15
    • 10444221780 scopus 로고    scopus 로고
    • LaBarbera, D. V.; Skibo, E. B. Synthesis of imidazo[1,5,4-de]- quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products. Bioorg. Med. Chem. 2004, 13 (2), 387-395.
    • LaBarbera, D. V.; Skibo, E. B. Synthesis of imidazo[1,5,4-de]- quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products. Bioorg. Med. Chem. 2004, 13 (2), 387-395.
  • 16
    • 0024312538 scopus 로고
    • Display and analysis of differential activity of drugs against human tumor cell lines: Development of mean graph and COMPARE algorithm
    • Pauil, D. K.; Shoemaker, R. H.; Hodes, L.; Monks, A.; Scudiero, D. A.; Rubinstein, L.; Plowman, J.; Boyd, M. R. Display and analysis of differential activity of drugs against human tumor cell lines: Development of mean graph and COMPARE algorithm. J. Natl. Cancer Inst. 1989, 81, 1088-1092.
    • (1989) J. Natl. Cancer Inst , vol.81 , pp. 1088-1092
    • Pauil, D.K.1    Shoemaker, R.H.2    Hodes, L.3    Monks, A.4    Scudiero, D.A.5    Rubinstein, L.6    Plowman, J.7    Boyd, M.R.8
  • 17
    • 0028137119 scopus 로고
    • Synthetic studies of the pyrroloquinoline nucleus of the makaluvamine alkaloids. Synthesis of the topoisomerase II inhibitor makaluvamine D
    • White, J. D.; Yager, K. M.; Yakura, T. Synthetic studies of the pyrroloquinoline nucleus of the makaluvamine alkaloids. Synthesis of the topoisomerase II inhibitor makaluvamine D. J. Am. Chem. Soc. 1994, 116, 1831-1838.
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 1831-1838
    • White, J.D.1    Yager, K.M.2    Yakura, T.3
  • 18
    • 37049127681 scopus 로고
    • Preparation of nitroquinols and their methyl ethers and benzenesulfonyl derivatives
    • Kampouris, E. M. Preparation of nitroquinols and their methyl ethers and benzenesulfonyl derivatives. J. Chem. Soc. C 1967, (13), 1235-1238.
    • (1967) J. Chem. Soc. C , vol.13 , pp. 1235-1238
    • Kampouris, E.M.1
  • 19
    • 37049167943 scopus 로고
    • The formation of 2-substituted benzimidazoles
    • Phillips, M. A. The formation of 2-substituted benzimidazoles. J. Chem. Soc. 1928, 2393-2399.
    • (1928) J. Chem. Soc , pp. 2393-2399
    • Phillips, M.A.1
  • 20
    • 33845455052 scopus 로고
    • Oxidations with potassium nitrosodisulfonate (Fremy's radical). The Teuber reaction
    • Zimmer, H.; Lankin, D. C.; Horgan, S. W. Oxidations with potassium nitrosodisulfonate (Fremy's radical). The Teuber reaction. Chem. Rev. 1971, 71, 229-246.
    • (1971) Chem. Rev , vol.71 , pp. 229-246
    • Zimmer, H.1    Lankin, D.C.2    Horgan, S.W.3
  • 21
    • 0000719887 scopus 로고
    • Status of the NCI Preclinical Antitumor Drug Discovery Screen
    • 3rd ed, DeVita, V. T, Hellman, S, Rosenberg, S. A, Eds, J. B. Lippincott: Phildelphia, PA
    • Boyd, M. R. Status of the NCI Preclinical Antitumor Drug Discovery Screen. In Principles and Practices of Oncology (PPO updates), 3rd ed.; DeVita, V. T., Hellman, S., Rosenberg, S. A., Eds.; J. B. Lippincott: Phildelphia, PA, 1989; Vol. 3, pp 1-12.
    • (1989) Principles and Practices of Oncology (PPO updates) , vol.3 , pp. 1-12
    • Boyd, M.R.1
  • 22
    • 0028906786 scopus 로고
    • Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen
    • Boyd, M. R.; Pauli, K. D. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen. Drug Dev. Res. 1995, 34, 91-109.
    • (1995) Drug Dev. Res , vol.34 , pp. 91-109
    • Boyd, M.R.1    Pauli, K.D.2
  • 23
    • 0035950137 scopus 로고    scopus 로고
    • Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: Structure-activity relationships for cytotoxicity and antitumor activity
    • Xing, C.; Skibo, E. B.; Dorr, R. T. Aziridinyl quinone antitumor agents based on indoles and cyclopent[b]indoles: Structure-activity relationships for cytotoxicity and antitumor activity. J. Med. Chem. 2001, 44, 3545-3562.
    • (2001) J. Med. Chem , vol.44 , pp. 3545-3562
    • Xing, C.1    Skibo, E.B.2    Dorr, R.T.3
  • 24
    • 0034597120 scopus 로고    scopus 로고
    • Synthesis and antiproliferative evaluation of 7-aminosubstituted pyrroloiminoquinone derivatives
    • Beneteau, V.; Pierre, A.; Pfeiffer, B.; Renard, P.; Besson, T. Synthesis and antiproliferative evaluation of 7-aminosubstituted pyrroloiminoquinone derivatives. Bioorg. Med. Chem. Lett. 2000, 10 (19), 2231-2234.
    • (2000) Bioorg. Med. Chem. Lett , vol.10 , Issue.19 , pp. 2231-2234
    • Beneteau, V.1    Pierre, A.2    Pfeiffer, B.3    Renard, P.4    Besson, T.5
  • 27
    • 5144226212 scopus 로고    scopus 로고
    • Mining our ABCs: Pharmacogenomic approach for evaluating transporter function in cancer drug resistance
    • Ross, D. D.; Doyle, L. A. Mining our ABCs: Pharmacogenomic approach for evaluating transporter function in cancer drug resistance. Cancer Cell 2004, 6 (2), 105-107.
    • (2004) Cancer Cell , vol.6 , Issue.2 , pp. 105-107
    • Ross, D.D.1    Doyle, L.A.2
  • 28
    • 1542616703 scopus 로고    scopus 로고
    • Proteins of the Bcl-2 family in apoptosis signalling: From mechanistic insights to therapeutic opportunities
    • Chan, S.-L.; Yu, V. C. Proteins of the Bcl-2 family in apoptosis signalling: from mechanistic insights to therapeutic opportunities. Clin. Exp. Pharmacol. Physiol. 2004, 31 (3), 119-128.
    • (2004) Clin. Exp. Pharmacol. Physiol , vol.31 , Issue.3 , pp. 119-128
    • Chan, S.-L.1    Yu, V.C.2
  • 32
    • 0000393418 scopus 로고    scopus 로고
    • Relevance of Tumor Models in Anticancer Drug Development
    • Krager Verlag: Germany
    • Hollingshead, M. G.; Plowman, J.; Alley, M.; Mayo, J.; Sausville, E. Relevance of Tumor Models in Anticancer Drug Development. In Contrib. Oncol.; Krager Verlag: Germany, 1999; pp 109-120.
    • (1999) Contrib. Oncol , pp. 109-120
    • Hollingshead, M.G.1    Plowman, J.2    Alley, M.3    Mayo, J.4    Sausville, E.5


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