메뉴 건너뛰기




Volumn 49, Issue 6, 2006, Pages 1910-1915

Synthesis and biological activity of 7-phenyl-6,9-dihydro-3H-pyrrolo[3,2-f] quinolin-9-ones: A new class of antimitotic agents devoid of aromatase activity

Author keywords

[No Author keywords available]

Indexed keywords

2 CARBOXYMETHYL 4 METHOXY 4 PHENYL 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (3' AMINO)PHENYL 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (3' BROMOPHENYL) 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (3' CYANOPHENYL) 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (3' METHOXYPHENYL) 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (3' METHYLPHENYL) 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (3' NITROPHENYL) 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 (4' CYANOPHENYL) 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 PHENYL 3 (DIETHYLAMINOETHYL) 6,9 DIHYDROPYRROLO[3,2 F]QUINOLIN 9 ONE; 7 PHENYL 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; 7 THIENYL 6,9 DIHYDRO 3H PYRROLO[3,2 F]QUINOLIN 9 ONE; AROMATASE; QUINOLINE DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG; VINBLASTINE; VINCA ALKALOID; VINCRISTINE;

EID: 33645380372     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0510676     Document Type: Article
Times cited : (61)

References (44)
  • 3
    • 0032568390 scopus 로고    scopus 로고
    • Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2′,3′,4′-substituted-1,2,3,4-tetrahydro-2-phenyl-4- quinolones as a new class of antimitotic antitumor agents
    • Xia, Y.; Yang, Z. Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S. C.; Hamel, E.; Hackl, T.; Lee, K. H. Antitumor Agents. 181. Synthesis and Biological Evaluation of 6,7,2′,3′,4′-Substituted-1,2,3,4-tetrahydro-2- phenyl-4-quinolones as a New Class of Antimitotic Antitumor Agents. J. Med. Chem. 1998, 41, 1155-62.
    • (1998) J. Med. Chem. , vol.41 , pp. 1155-1162
    • Xia, Y.1    Yang, Z.Y.2    Xia, P.3    Bastow, K.F.4    Tachibana, Y.5    Kuo, S.C.6    Hamel, E.7    Hackl, T.8    Lee, K.H.9
  • 4
    • 0028295948 scopus 로고
    • Antitumor agents. 150. 2′,3′,4′,5′,5,6,7- substituted 2-phenyl-4-quinolones and related compounds: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization
    • Li, L.; Wang, H. K.; Kuo, S. C.; Wu, T. S.; Lednicer, D.; Lin, C. M.; Hamel, E.; Lee, K. H. Antitumor Agents. 150. 2′,3′,4′, 5′,5,6,7-Substituted 2-Phenyl-4-quinolones and Related Compounds: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1994, 37, 1126-35.
    • (1994) J. Med. Chem. , vol.37 , pp. 1126-1135
    • Li, L.1    Wang, H.K.2    Kuo, S.C.3    Wu, T.S.4    Lednicer, D.5    Lin, C.M.6    Hamel, E.7    Lee, K.H.8
  • 5
    • 0028036429 scopus 로고
    • Antitumor agents. 155. Synthesis and biological evaluation of 3′,6,7-substituted 2-phenyl-4-quinolones as antimicrotubule agents
    • Li, L.; Wang, H. K.; Kuo, S. C.; Wu, T. S.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K. H. Antitumor Agents. 155. Synthesis and Biological Evaluation of 3′,6,7-Substituted 2-phenyl-4-quinolones as Antimicrotubule Agents. J. Med. Chem. 1994, 37, 3400-07.
    • (1994) J. Med. Chem. , vol.37 , pp. 3400-3407
    • Li, L.1    Wang, H.K.2    Kuo, S.C.3    Wu, T.S.4    Mauger, A.5    Lin, C.M.6    Hamel, E.7    Lee, K.H.8
  • 6
    • 0027246046 scopus 로고
    • Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4′-substituted phenyl)-4-quinolones and related compounds: Identification as antimitotic agents interacting with tubulin
    • Kuo, S. C.; Lee, H. Z.; Juang, J. P.; Lin, Y. T.; Wu, T. S.; Chang, J. J.; Lednicer, D.; Paull, K. D.; Lin, C. M.; Hamel, E.; Lee, K. H. Synthesis and Cytotoxicity of 1,6,7,8-Substituted 2-(4′-Substituted phenyl)-4-quinolones and Related Compounds: Identification as Antimitotic Agents Interacting with Tubulin. J. Med. Chem. 1993, 36, 1146-56.
    • (1993) J. Med. Chem. , vol.36 , pp. 1146-1156
    • Kuo, S.C.1    Lee, H.Z.2    Juang, J.P.3    Lin, Y.T.4    Wu, T.S.5    Chang, J.J.6    Lednicer, D.7    Paull, K.D.8    Lin, C.M.9    Hamel, E.10    Lee, K.H.11
  • 7
    • 0342302387 scopus 로고
    • New synthesis of 2-aryl-4-quinolones
    • Kasahara, A.; Izumi, A. New Synthesis of 2-Aryl-4-Quinolones. Chem. Ind. (London) 1981, 4, 121.
    • (1981) Chem. Ind. (London) , vol.4 , pp. 121
    • Kasahara, A.1    Izumi, A.2
  • 8
    • 0030048231 scopus 로고    scopus 로고
    • Antitumor 2,3-dihydro-2-(aryl)-4(1H)-quinazolinone derivatives. Interactions with tubulin
    • Hamel, E.; Lin, C. M.; Plowman, J.; Wang, H. K.; Lee, K. H.; Paull, K. D. Antitumor 2,3-Dihydro-2-(aryl)-4(1H)-quinazolinone Derivatives. Interactions with Tubulin. Biochem. Pharmacol. 1996, 51, 53-9.
    • (1996) Biochem. Pharmacol. , vol.51 , pp. 53-59
    • Hamel, E.1    Lin, C.M.2    Plowman, J.3    Wang, H.K.4    Lee, K.H.5    Paull, K.D.6
  • 9
    • 0025836773 scopus 로고
    • Investigation of the mechanism of the interaction of tubulin with derivatives of 2-styrylquinazolin-4(3H)-one
    • Lin, C. M.; Kang, G. J.; Roach, M. C.; Jiang, J. B.; Hesson, D. P.; Luduena, R. F.; Hamel, E. Investigation of the Mechanism of the Interaction of Tubulin with Derivatives of 2-Styrylquinazolin-4(3H)-one. Mol. Pharmacol. 1991, 40, 827-32.
    • (1991) Mol. Pharmacol. , vol.40 , pp. 827-832
    • Lin, C.M.1    Kang, G.J.2    Roach, M.C.3    Jiang, J.B.4    Hesson, D.P.5    Luduena, R.F.6    Hamel, E.7
  • 10
    • 0025302762 scopus 로고
    • Synthesis and biological evaluation of 2-styryl-quinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization
    • Jiang, J. B.; Hesson, D. P.; Dusak, B. A.; Dexter, D. L.; Kang, G. J.; Hamel, E. Synthesis and Biological Evaluation of 2-Styryl-quinazolin-4(3H)-ones, a New Class of Antimitotic Anticancer Agents Which Inhibit Tubulin Polymerization. J. Med. Chem. 1990, 33, 1721-28.
    • (1990) J. Med. Chem. , vol.33 , pp. 1721-1728
    • Jiang, J.B.1    Hesson, D.P.2    Dusak, B.A.3    Dexter, D.L.4    Kang, G.J.5    Hamel, E.6
  • 11
    • 0015329105 scopus 로고
    • Antitumor effects of the antispermatogenic agent, 2,3-dihydro-2-(1- naphthyl)-4(1H)-quinazolinone
    • Neil, G. L.; Li, L. H.; Buskirk, H. H.; Moxley, T. E. Antitumor effects of the antispermatogenic agent, 2,3-dihydro-2-(1-naphthyl)-4(1H)-quinazolinone. Cancer Chemother. 1972, 56, 163-73.
    • (1972) Cancer Chemother. , vol.56 , pp. 163-173
    • Neil, G.L.1    Li, L.H.2    Buskirk, H.H.3    Moxley, T.E.4
  • 12
    • 0000091591 scopus 로고
    • Substituted 2,3-dihydro-4-(1H)-quinazolinones. A new class of inhibitors of cell multiplication
    • Yale, H. J.; Kalkstein, M. Substituted 2,3-Dihydro-4-(1H)-quinazolinones. A New Class of Inhibitors of Cell Multiplication. J. Med. Chem. 1967, 10, 334-36.
    • (1967) J. Med. Chem. , vol.10 , pp. 334-336
    • Yale, H.J.1    Kalkstein, M.2
  • 13
    • 0033533865 scopus 로고    scopus 로고
    • Antitumor agents. 196. Substituted 2-thienyl-1,8-naphthyridin-4-ones: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization
    • Zhang, S. X.; Bastow, K. F.; Tachibana, Y.; Kuo, S. C.; Hamel, E.; Mauger, A.; Narayanan, V. L.; Lee, K. H. Antitumor Agents. 196. Substituted 2-Thienyl-1,8-naphthyridin-4-ones: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1999, 42, 4081-87.
    • (1999) J. Med. Chem. , vol.42 , pp. 4081-4087
    • Zhang, S.X.1    Bastow, K.F.2    Tachibana, Y.3    Kuo, S.C.4    Hamel, E.5    Mauger, A.6    Narayanan, V.L.7    Lee, K.H.8
  • 14
    • 0030738726 scopus 로고    scopus 로고
    • Antitumor agents. 174. 2′,3′,4′,5,6,7-substituted 2-phenyl-1,8-naphthyridin-4-ones: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization
    • Chen, K.; Kuo, S. C.; Hsieh, M. C.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K. H. Antitumor Agents. 174. 2′,3′,4′,5,6,7-Substituted 2-Phenyl-1,8-naphthyridin-4-ones: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1997, 40, 2266-75.
    • (1997) J. Med. Chem. , vol.40 , pp. 2266-2275
    • Chen, K.1    Kuo, S.C.2    Hsieh, M.C.3    Mauger, A.4    Lin, C.M.5    Hamel, E.6    Lee, K.H.7
  • 15
    • 0030823308 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of substituted 2-aryl-1,8- naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization
    • Chen, K.; Kuo, S. C.; Hsieh, M. C.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K. H. Synthesis and Biological Evaluation of Substituted 2-Aryl-1,8-naphthyridin-4(1H)-ones as Antitumor Agents That Inhibit Tubulin Polymerization. J. Med. Chem. 1997, 40, 3049-56.
    • (1997) J. Med. Chem. , vol.40 , pp. 3049-3056
    • Chen, K.1    Kuo, S.C.2    Hsieh, M.C.3    Mauger, A.4    Lin, C.M.5    Hamel, E.6    Lee, K.H.7
  • 16
    • 0034719321 scopus 로고    scopus 로고
    • Antitumor agents. 199. Three-dimensional quantitative structure-activity relationship study of the colchicine binding site ligands using comparative molecular field analysis
    • Zhang, S. X.; Feng, J.; Kuo, S. C.; Brossi, A.; Hamel, E.; Tropsha, A.; Lee, K. H. Antitumor Agents. 199. Three-Dimensional Quantitative Structure-Activity Relationship Study of the Colchicine Binding Site Ligands Using Comparative Molecular Field Analysis. J. Med. Chem. 2000, 43, 167-76.
    • (2000) J. Med. Chem. , vol.43 , pp. 167-176
    • Zhang, S.X.1    Feng, J.2    Kuo, S.C.3    Brossi, A.4    Hamel, E.5    Tropsha, A.6    Lee, K.H.7
  • 17
  • 18
    • 18844443185 scopus 로고    scopus 로고
    • Aromatase inhibitors in the treatment of breast cancer
    • Brueggemeier, R. W.; Hackett, J. C.; Diaz-Cruz, E. S. Aromatase Inhibitors in the Treatment of Breast Cancer. Endocr. Rev. 2005, 26 (3), 331-45.
    • (2005) Endocr. Rev. , vol.26 , Issue.3 , pp. 331-345
    • Brueggemeier, R.W.1    Hackett, J.C.2    Diaz-Cruz, E.S.3
  • 21
    • 0033141561 scopus 로고    scopus 로고
    • Inhibition of aromatase activity by flavonoids
    • Jeong, H.-J.; Shin, Y. G. Inhibition of aromatase activity by flavonoids. Arch. Pharm. Res. 1999, 22, 309-12.
    • (1999) Arch. Pharm. Res. , vol.22 , pp. 309-312
    • Jeong, H.-J.1    Shin, Y.G.2
  • 22
    • 0037154405 scopus 로고    scopus 로고
    • Flavonoid-potent and versatile biologically active compounds interacting with cytochromes P450
    • Hodek, P.; Trefil, P.; Stiborova, M. Flavonoid-potent and versatile biologically active compounds interacting with cytochromes P450. Chem. Biol. Interact. 2002, 139, 1-21.
    • (2002) Chem. Biol. Interact. , vol.139 , pp. 1-21
    • Hodek, P.1    Trefil, P.2    Stiborova, M.3
  • 23
    • 8444243681 scopus 로고    scopus 로고
    • Inductiction and inhibition of aromatase (Cyp19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells
    • Sanderson, J. T.; Hordijk, J.; Denison, M. S.; Springsteel, M. F.; Nantz, M. H.; Van den Berg, M. Inductiction and Inhibition of Aromatase (Cyp19) Activity by Natural and Synthetic Flavonoid Compounds in H295R Human Adrenocortical Carcinoma Cells. Toxicol. Sci. 2004, 82, 70-9.
    • (2004) Toxicol. Sci. , vol.82 , pp. 70-79
    • Sanderson, J.T.1    Hordijk, J.2    Denison, M.S.3    Springsteel, M.F.4    Nantz, M.H.5    Van Den Berg, M.6
  • 24
    • 0020448021 scopus 로고
    • Studies on ketene and its derivatives. CX. Synthesis of 1,3-dimethoxyfluoren-9-ones
    • Nakano, J.; Katagiri, N.; Kato, T. Studies on Ketene and Its Derivatives. CX. Synthesis of 1,3-Dimethoxyfluoren-9-ones. Chem. Pharm. Bull. 1982, 30, 1, 2590-4.
    • (1982) Chem. Pharm. Bull. , vol.30 , Issue.1 , pp. 2590-2594
    • Nakano, J.1    Katagiri, N.2    Kato, T.3
  • 26
    • 33645401223 scopus 로고
    • Ber. 1891, 24, 2990.
    • (1891) Ber. , vol.24 , pp. 2990
  • 29
    • 0037048763 scopus 로고    scopus 로고
    • Antiproliferative activities of citrus flavonoids against six human cancer cell lines
    • Manthey, J. A.; Guthrie, N. Antiproliferative Activities of Citrus Flavonoids against Six Human Cancer Cell Lines. J. Agric. Food Chem. 2002, 50, 5837-43.
    • (2002) J. Agric. Food Chem. , vol.50 , pp. 5837-5843
    • Manthey, J.A.1    Guthrie, N.2
  • 30
    • 0036238085 scopus 로고    scopus 로고
    • Nonsteroidal aromatase inhibitors: Recent advances
    • Recanatini, M.; Cavalli, A.; Valenti, P. Nonsteroidal Aromatase Inhibitors: Recent Advances. Med. Res. Rev. 2002, 22, 3, 282-304.
    • (2002) Med. Res. Rev. , vol.22 , Issue.3 , pp. 282-304
    • Recanatini, M.1    Cavalli, A.2    Valenti, P.3
  • 31
    • 0030076102 scopus 로고    scopus 로고
    • Comparative molecular field analysis of non-steroidal aromatase inhibitors related to fadrozole
    • Recanatini, M. Comparative Molecular Field Analysis of Non-Steroidal Aromatase Inhibitors Related To Fadrozole. J. Comput.-Aided Mol. Des. 1996, 10, 74-82.
    • (1996) J. Comput.-Aided Mol. Des. , vol.10 , pp. 74-82
    • Recanatini, M.1
  • 36
    • 3042740981 scopus 로고    scopus 로고
    • BPR0L075, a novel synthetic indole compound with antimitotic activity in human cancer cells, exerts effective antitumoral activity in vivo
    • Kuo, C. C.; Hsieh, H. P.; Pan, W. Y.; Chen, C. P.; Liou, J. P.; Lee, S. J.; Chang, Y. L.; Chen, L. T.; Chen, C. T.; Chang, J. Y. BPR0L075, a Novel Synthetic Indole Compound with Antimitotic Activity in Human Cancer Cells, Exerts Effective Antitumoral Activity in Vivo. Cancer Res. 2004, 64, 4621-8.
    • (2004) Cancer Res. , vol.64 , pp. 4621-4628
    • Kuo, C.C.1    Hsieh, H.P.2    Pan, W.Y.3    Chen, C.P.4    Liou, J.P.5    Lee, S.J.6    Chang, Y.L.7    Chen, L.T.8    Chen, C.T.9    Chang, J.Y.10
  • 37
    • 1642495631 scopus 로고    scopus 로고
    • Salvinal, a novel microtubule inhibitor isolated from salvia miltiorrhizae bunge (danshen), with antimitotic activity in multidrug-sensitive and -resistant human tumor cells
    • Chang, J. Y.; Chang, C. Y.; Kuo, C. C.; Chen, L. T.; Wein, Y. S.; Kuo, Y. H. Salvinal, a Novel Microtubule Inhibitor Isolated from Salvia miltiorrhizae Bunge (Danshen), with Antimitotic Activity in Multidrug-Sensitive and -Resistant Human Tumor Cells. Mol. Pharmacol. 2004, 65, 77-84.
    • (2004) Mol. Pharmacol. , vol.65 , pp. 77-84
    • Chang, J.Y.1    Chang, C.Y.2    Kuo, C.C.3    Chen, L.T.4    Wein, Y.S.5    Kuo, Y.H.6
  • 38
    • 0036257468 scopus 로고    scopus 로고
    • Antitumor activity of Z-ajoene. A natural compound purified from garlic: Antimitotic and microtubule-interaction properties
    • Li, M.; Ciu, J.-R.; Ye, Y.; Min, J.-M.; Zhang, L.-H.; Wang, K.; Gares, M.; Cros, J.; Wright, M.; Leung-Tack, J. Antitumor Activity of Z-ajoene. a Natural Compound Purified from Garlic: Antimitotic and Microtubule-Interaction Properties. Carcinogenesis 2002, 23, 4, 573-9.
    • (2002) Carcinogenesis , vol.23 , Issue.4 , pp. 573-579
    • Li, M.1    Ciu, J.-R.2    Ye, Y.3    Min, J.-M.4    Zhang, L.-H.5    Wang, K.6    Gares, M.7    Cros, J.8    Wright, M.9    Leung-Tack, J.10
  • 39
    • 4644316617 scopus 로고    scopus 로고
    • The tubulin-binding agent combretastatin A-4-phosphate arrests endothelial cells in mitosis and induces mitotic cell death
    • Kanthou, C.; Greco, O.; Stratford, A.; Cook, I.; Knight, R.; Benzakour, O.; Tozer, G. The Tubulin-Binding Agent Combretastatin A-4-Phosphate Arrests Endothelial Cells in Mitosis and Induces Mitotic Cell Death. Am. J. Pathol. 2004, 165, 4, 1401-11.
    • (2004) Am. J. Pathol. , vol.165 , Issue.4 , pp. 1401-1411
    • Kanthou, C.1    Greco, O.2    Stratford, A.3    Cook, I.4    Knight, R.5    Benzakour, O.6    Tozer, G.7
  • 40
    • 2342476494 scopus 로고    scopus 로고
    • Bisphenol A and its methylated congeners inhibit growth and interfere with microtubules in human fibroblast in vitro
    • Lehmann, L.; Metzler, M. Bisphenol A and Its Methylated Congeners Inhibit Growth and Interfere with Microtubules in Human Fibroblast in Vitro. Chem.-Biol. Internet. 2004, 147, 273-285.
    • (2004) Chem.-Biol. Internet. , vol.147 , pp. 273-285
    • Lehmann, L.1    Metzler, M.2
  • 41
    • 0002453760 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 1,1-dichloro-2,3- diarylcyclopropanes as antitubulin and anti-breast cancer agents
    • Jonnalagadda, S. S.; ter Haar, E.; Hamel, E.; Lin, C. M.; Magarian, R. A.; Day, B. W. Synthesis and Biological Evaluation of 1,1-Dichloro-2,3- diarylcyclopropanes as Antitubulin and Anti-breast Cancer Agents. Bioorg., Med. Chem. 1997, 5, 715-22.
    • (1997) Bioorg., Med. Chem. , vol.5 , pp. 715-722
    • Jonnalagadda, S.S.1    Ter Haar, E.2    Hamel, E.3    Lin, C.M.4    Magarian, R.A.5    Day, B.W.6
  • 43
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. A Rapid and Sensitive Method for the Quantitation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding. Anal. Biochem. 1976, 72, 248-54.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.