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Volumn 46, Issue 14, 2003, Pages 3072-3082

Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 2 ACYLOXY 6 METHYOXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE DERIVATIVE; 1 METHOXY 2 ACETOXY 6 METHOXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 1,2 DIACETOXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 1,2 DIACYLOXY 6 METHOXY 3,3,14 TRIMETHYL 1,2,3 14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE DERIVATIVE; 2 ACETOXY 6 METHOXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 1,7 DIONE; 2 ACETOXY 6 METHOXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 DI O CARBONYL 1,2 DIHYDROXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 PROPIOXY 6 METHOXY 1,1,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDINE 1,7 DIONE; 3 BROMO 2 NAPHTHOIC ACID; 4 AMINO 2,2 DIMETHYL 2H CHROMENE; 6 DEMETHOXYACRONINE DERIVATIVE; ACRONINE; ANTINEOPLASTIC AGENT; BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE DERIVATIVE; CHROMENE DERIVATIVE; ESTER; GENOMIC DNA; GUANINE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037698962     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030790y     Document Type: Article
Times cited : (58)

References (30)
  • 1
    • 33751062476 scopus 로고
    • Alkaloids of the Australian rutaceae
    • (a) Hughes, G. K.; Lahey, F. N.; Price J. R. Alkaloids of the Australian Rutaceae. Nature 1948, 162, 223-224.
    • (1948) Nature , vol.162 , pp. 223-224
    • Hughes, G.K.1    Lahey, F.N.2    Price, J.R.3
  • 3
    • 0000084155 scopus 로고
    • Alkaloids of Glycosmis pentaphylla (Retz.) correa
    • (c) Govindachari, T. R.; Pai, B. R.; Subramaniam, P. S. Alkaloids of Glycosmis pentaphylla (Retz.) Correa. Tetrahedron 1966, 22, 3245-3252.
    • (1966) Tetrahedron , vol.22 , pp. 3245-3252
    • Govindachari, T.R.1    Pai, B.R.2    Subramaniam, P.S.3
  • 4
    • 0001305174 scopus 로고
    • The crystal and molecular structure of bromodihydroacronycine
    • (d) Gougoutas, J. Z.; Kaski, B. A. The crystal and molecular structure of bromodihydroacronycine. Acta Crystallogr. 1970, B26, 853-859.
    • (1970) Acta Crystallogr. , vol.B26 , pp. 853-859
    • Gougoutas, J.Z.1    Kaski, B.A.2
  • 6
    • 0001139190 scopus 로고
    • Alkaloids of Acronychia baueri. Extraction of the alkaloids and studies of structure-activity relationships
    • (a) Svoboda, G. H. Alkaloids of Acronychia baueri. Extraction of the alkaloids and studies of structure-activity relationships. Lloydia 1966, 29, 206-224.
    • (1966) Lloydia , vol.29 , pp. 206-224
    • Svoboda, G.H.1
  • 7
    • 0013937331 scopus 로고
    • Alkaloids of Acronychia baueri. Isolation of the alkaloids and study of the antitumor and other biological properties of acronycine
    • (b) Svoboda, G. H.; Poore, G. A.; Simpson, P. J.; Boder, G. B. Alkaloids of Acronychia baueri. Isolation of the alkaloids and study of the antitumor and other biological properties of acronycine. J. Pharm. Sci., 1966, 55, 758-768.
    • (1966) J. Pharm. Sci. , vol.55 , pp. 758-768
    • Svoboda, G.H.1    Poore, G.A.2    Simpson, P.J.3    Boder, G.B.4
  • 8
    • 0024496679 scopus 로고
    • Antitumor activity and murine pharmacokinetics of parenteral acronycine
    • (c) Dorr, R. T.; Liddil, J. D.; Von Hoff, D. D.; Soble, M.; Osborne, C. K. Antitumor activity and murine pharmacokinetics of parenteral acronycine. Cancer Res. 1989, 49, 340-344.
    • (1989) Cancer Res. , vol.49 , pp. 340-344
    • Dorr, R.T.1    Liddil, J.D.2    Von Hoff, D.D.3    Soble, M.4    Osborne, C.K.5
  • 9
    • 0020696419 scopus 로고
    • Phase I-II evaluation of acronycine in patients with multiple myeloma
    • Scarffe, J. H.; Beaumont, A. R.; Crowther, D. Phase I-II evaluation of acronycine in patients with multiple myeloma. Cancer Treat. Rep. 1983, 67, 93-94.
    • (1983) Cancer Treat. Rep. , vol.67 , pp. 93-94
    • Scarffe, J.H.1    Beaumont, A.R.2    Crowther, D.3
  • 10
  • 12
  • 13
    • 0032916316 scopus 로고    scopus 로고
    • Chiral dihydroxylation of acronycine: Absolute configuration of natural cis-1,2-dihydroxy-1,2-dihydroacronycine and cytotoxicity of (1R,2R) and (1S,2S)-1,2-diacetoxy1,2-dihydroacronycine
    • (c) Costes, N.; Michel, S., Tillequin, F.; Koch, M.; Pierré, A.; Atassi, Gh. Chiral dihydroxylation of acronycine: absolute configuration of natural cis-1,2-dihydroxy-1,2-dihydroacronycine and cytotoxicity of (1R,2R) and (1S,2S)-1,2-diacetoxy1,2-dihydroacronycine. J. Nat. Prod. 1999, 62, 490-492.
    • (1999) J. Nat. Prod. , vol.62 , pp. 490-492
    • Costes, N.1    Michel, S.2    Tillequin, F.3    Koch, M.4    Pierré, A.5    Atassi, Gh.6
  • 18
    • 0035213896 scopus 로고    scopus 로고
    • Induction of cyclin E and inhibition of DNA synthesis by the novel acronycine derivative S-23906-1 precede the irreversible arrest of tumor cells in S phase leading to apoptosis
    • Léonce, S.; Pérez, V.; Lambel, S.; Peyroulan, D.; Tillequin, F.; Michel, S.; Koch, M.; Pfeiffer, B.; Atassi, Gh.; Hickman, J.; Pierré, A. Induction of cyclin E and inhibition of DNA synthesis by the novel acronycine derivative S-23906-1 precede the irreversible arrest of tumor cells in S phase leading to apoptosis. Mol. Pharmacol. 2001, 60, 1383-1391.
    • (2001) Mol. Pharmacol. , vol.60 , pp. 1383-1391
    • Léonce, S.1    Pérez, V.2    Lambel, S.3    Peyroulan, D.4    Tillequin, F.5    Michel, S.6    Koch, M.7    Pfeiffer, B.8    Atassi, Gh.9    Hickman, J.10    Pierré, A.11
  • 19
    • 0032994276 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of 1-alkoxy- and 1-amino-2-hydroxy-dihydroxy-1,2-dihydroacronycine derivatives
    • Magiatis, P. Mitaku, S.; Skaltsounis, A.-L.; Tillequin, F.; Koch, M.; Pierré, A.; Atassi, Gh. Synthesis and cytotoxic activity of 1-alkoxy- and 1-amino-2-hydroxy-dihydroxy-1,2-dihydroacronycine derivatives. Chem. Pharm. Bull. 1999, 47, 611-614.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 611-614
    • Magiatis, P.1    Mitaku, S.2    Skaltsounis, A.-L.3    Tillequin, F.4    Koch, M.5    Pierré, A.6    Atassi, Gh.7
  • 20
    • 85008586169 scopus 로고
    • New carbazolequinones having dimethylpyran ring system from Murraya euchrestifolia
    • (a) Furukawa, H.; Yogo, M.; Ito, C.; Wu, T.-S.; Kuoh, C.-S. New carbazolequinones having dimethylpyran ring system from Murraya euchrestifolia. Chem. Pharm. Bull. 1985, 33, 1320-1322.
    • (1985) Chem. Pharm. Bull. , vol.33 , pp. 1320-1322
    • Furukawa, H.1    Yogo, M.2    Ito, C.3    Wu, T.-S.4    Kuoh, C.-S.5
  • 21
    • 0026028142 scopus 로고
    • Synthesis of some carbazolequinone alkaloids and their analogues. Facile palladium-assisted intramolecular ring closure of arylamino-1,4-benzoquinones to carbazole-1,4-quinones
    • (b) Yogo, M.; Ito, C.; Furukawa, H. Synthesis of some carbazolequinone alkaloids and their analogues. Facile palladium-assisted intramolecular ring closure of arylamino-1,4-benzoquinones to carbazole-1,4-quinones. Chem. Pharm. Bull. 1991, 39, 328-334.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 328-334
    • Yogo, M.1    Ito, C.2    Furukawa, H.3
  • 22
    • 44049117171 scopus 로고
    • A novel synthesis of 6-demethoxyacronycine
    • (c) Elomri, A.; Michel, S.; Tillequin, F.; Koch, M. A novel synthesis of 6-demethoxyacronycine. Heterocycles 1992, 34, 799-806.
    • (1992) Heterocycles , vol.34 , pp. 799-806
    • Elomri, A.1    Michel, S.2    Tillequin, F.3    Koch, M.4
  • 23
    • 0038237599 scopus 로고
    • A relationship between β-naphthylamine and ethyl β-aminocrotonate
    • Kenner, J.; Ritchie, W. H.; Wain, R. L. A relationship between β-naphthylamine and ethyl β-aminocrotonate. J. Chem. Soc. 1937, 1526-1529.
    • (1937) J. Chem. Soc. , pp. 1526-1529
    • Kenner, J.1    Ritchie, W.H.2    Wain, R.L.3
  • 24
    • 0024997709 scopus 로고
    • Synthesis of des-N-methylacronycine and acronycine
    • (a) Loughhead D. G. Synthesis of des-N-methylacronycine and acronycine. J. Org. Chem. 1990, 55, 2245-2246.
    • (1990) J. Org. Chem. , vol.55 , pp. 2245-2246
    • Loughhead, D.G.1
  • 25
    • 0033405425 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of 11-nitro and 11-amino derivatives of acronycine and 6-demethoxyacronycine
    • (b) Elomri, A.; Michel, S.; Koch, M.; Seguin, E.; Tillequin, F.; Pierré, A.; Atassi, Gh. Synthesis and cytotoxic activity of 11-nitro and 11-amino derivatives of acronycine and 6-demethoxyacronycine. Chem. Pharm. Bull. 1999, 47, 1604-1606.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 1604-1606
    • Elomri, A.1    Michel, S.2    Koch, M.3    Seguin, E.4    Tillequin, F.5    Pierré, A.6    Atassi, Gh.7
  • 26
    • 49549130554 scopus 로고
    • 4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant
    • 4 oxidation of olefins to cis-1,2-glycols using tertiary amine oxides as the oxidant. Tetrahedron Lett. 1976, 23, 1973-1976.
    • (1976) Tetrahedron Lett. , vol.23 , pp. 1973-1976
    • Rheenen, V.V.1    Kelly, R.C.2    Cha, D.Y.3
  • 27
    • 0038237557 scopus 로고    scopus 로고
    • Synthesis of 6-dialkylaminialkylamino pyrano[2,3-c]acridones and benzo[b]pyrano[3,2-h]acridones; soluble acronycine analogues with increased cytotoxic activity
    • Costes, N.; Elomri, A.; Dufat, H.; Michel, S., Seguin, E.; Koch, M.; Tillequin, F.; Pfeiffer, B.; Renard, P.; Léonce, S.; Pierré, A. Synthesis of 6-dialkylaminialkylamino pyrano[2,3-c]acridones and benzo[b]pyrano[3,2-h]acridones; soluble acronycine analogues with increased cytotoxic activity. Oncology Res. 2003, 13, 191-197.
    • (2003) Oncology Res. , vol.13 , pp. 191-197
    • Costes, N.1    Elomri, A.2    Dufat, H.3    Michel, S.4    Seguin, E.5    Koch, M.6    Tillequin, F.7    Pfeiffer, B.8    Renard, P.9    Léonce, S.10    Pierré, A.11
  • 29
    • 0026457778 scopus 로고
    • Effects of a new triazinoaminopiperidine derivative on adriamycin accumulation and retention in cells displaying P-glycoprotein-mediated multidrug resistance
    • (a) Leonce, S.; Pierré, A.; Anstett, M.; Perez, V.; Genton, A.; Bizzari, J. P.; Atassi, Gh. Effects of a new triazinoaminopiperidine derivative on adriamycin accumulation and retention in cells displaying P-glycoprotein-mediated multidrug resistance. Bio-Chem. Pharmacol. 1992, 44, 1707.
    • (1992) Bio-Chem. Pharmacol. , vol.44 , pp. 1707
    • Leonce, S.1    Pierré, A.2    Anstett, M.3    Perez, V.4    Genton, A.5    Bizzari, J.P.6    Atassi, Gh.7


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