메뉴 건너뛰기




Volumn 46, Issue 12, 2011, Pages 6046-6056

Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs

Author keywords

Anticancer activity; Melanoma; Quinolin 4 one analogs; Selenophene; Structure activity relationships (SAR)

Indexed keywords

2 (2 FLUOROPHENYL) 6,7 METHYLENEDIOXYQUINOLIN 4 ONE; 2 (3 FLUOROPHENYL) 5 HYDROXY 6 METHOXYQUINOLIN 4 ONE; 2 (5 METHYLFURAN 2 YL) 6,7 METHYLENEDIOXYQUINOLIN 4 ONE; 2 (5 METHYLSELENOPHEN 2 YL) 6,7 METHYLENEDIOXYQUINOLIN 4 ONE; 2 (5 METHYLTHIOPHEN 2 YL) 6,7 METHYLENEDIOXYQUINOLIN 4 ONE; 2 (FURAN 2 YL) 6,7 METHYLENEDIOXYQUINOLIN 4 ON; 2 (FURAN 3 YL) 6,7 METHYLENEDIOXYQUINOLIN 4 ON; 5 HYDROXY 2 (5 METHYLSELENOPHEN 2 YL) 6 METHOXYQUINOLIN 4 ONE; 5 HYDROXY 6 METHOXY 2 (SELENOPHEN 3 YL)QUINOLIN 4 ONE; 5,6 DIMETHOXY 2 (5 METHYLSELENOPHEN 2 YL)QUINOLIN 4 ONE; 5,6 DIMETHOXY 2 (SELENOPHEN 2 YL)QUINOLIN 4 ONE; 5,6 DIMETHOXY 2 (SELENOPHEN 3 YL)QUINOLIN 4 ON; 6 DIMETHOXY 2 (SELENOPHEN 2 YL)QUINOLIN 4 ONE; 6 METHOXY 2 (5 METHYLSELENOPHEN 2 YL)QUINOLIN 4 ONE; 6 METHOXY 2 (SELENOPHEN 3 YL)QUINOLIN 4 ONE; 6,7 METHYLENEDIOXY 2 (5 METHYLSELENOPHEN 2YL)QUINOLIN 4 ONE; 6,7 METHYLENEDIOXY 2 (SELENOPHEN 2 YL)QUINOLIN 4 ONE; 6,7 METHYLENEDIOXY 2 (SELENOPHEN 3 YL)QUINOLIN 4 ONE; 6,7 METHYLENEDIOXY 2 (THIOPHEN 2 YL)QUINOLIN 4 ONE; 6,7 METHYLENEDIOXY 2 (THIOPHEN 3 YL)QUINOLIN 4 ONE; ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; COLCHICINE; DIDEMNIN B; PACLITAXEL; S TRITYLCYSTEINE; UNCLASSIFIED DRUG; VINBLASTINE; VINCRISTINE;

EID: 80955151714     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.017     Document Type: Article
Times cited : (34)

References (30)
  • 1
    • 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
    • DOI 10.1021/jm00061a005
    • S.C. Kuo, H.Z. Lee, J.P. Juang, Y.T. Lin, T.S. Wu, J.J. Chang, D. Lednicer, K.D. Pad, C.M. Lin, E. Hamel, and K.H. Lee 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. 36 1993 1146 1156 (Pubitemid 23159288)
    • (1993) Journal of Medicinal Chemistry , vol.36 , Issue.9 , 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
  • 2
    • 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
    • L. Li, H.K. Wang, S.C. Kuo, T.S. Wu, D. Lednicer, C.M. Lin, E. Hamel, and K.H. Lee 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. 37 1994 1126 1135 (Pubitemid 24145373)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.8 , 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
  • 3
    • 0028036429 scopus 로고
    • Antitumor agents 155. Synthesis and biological evaluation of 3',6,7- substituted 2-phenyl-4-quinolones as antimicrotubule agents
    • DOI 10.1021/jm00046a025
    • L. Li, H.K. Wang, S.C. Kuo, T.S. Wu, A. Mauger, C.M. Lin, E. Hamel, and K.H. Lee Antitumor agents. 155. Synthesis and biological evaluation of 3′,6,7-substituted 2-phenyl-4-quinolones as antimicrotubule agents J. Med. Chem. 37 1994 3400 3407 (Pubitemid 24325054)
    • (1994) Journal of Medicinal Chemistry , vol.37 , Issue.20 , 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
  • 5
    • 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
    • DOI 10.1021/jm9707479
    • Y. Xia, Z.Y. Yang, P. Xia, K.F. Bastow, Y. Tachibana, S.C. Kuo, E. Hamel, T. Hackl, and K.H. Lee 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. 41 1998 1155 1162 (Pubitemid 28207391)
    • (1998) Journal of Medicinal Chemistry , vol.41 , Issue.7 , 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
  • 6
    • 9644266706 scopus 로고    scopus 로고
    • Synthesis and biological relationships of 3,6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents
    • DOI 10.1016/j.bmc.2004.09.041, PII S0968089604007382
    • Y.Y. Lai, L.J. Huang, K.H. Lee, Z. Xiao, K.F. Bastow, T. Yamori, and S.C. Kuo Synthesis and biological relationships of 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents Bioorg. Med. Chem. 13 2005 265 275 (Pubitemid 39575710)
    • (2005) Bioorganic and Medicinal Chemistry , vol.13 , Issue.1 , pp. 265-275
    • Lai, Y.-Y.1    Huang, L.-J.2    Lee, K.-H.3    Xiao, Z.4    Bastow, K.F.5    Yamori, T.6    Kuo, S.-C.7
  • 7
    • 68549110382 scopus 로고    scopus 로고
    • Design and synthesis of 2-(3-benzo[b]thienyl)-6,7-methylenedioxyquinolin- 4-one analogs as potent antitumor agents that inhibit tubulin assembly
    • Y.H. Chang, M.H. Hsu, S.H. Wang, L.J. Huang, K. Qian, S.L. Morris-Natschke, E. Hamel, S.C. Kuo, and K.H. Lee Design and synthesis of 2-(3-benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one analogs as potent antitumor agents that inhibit tubulin assembly J. Med. Chem. 52 2009 4883 4891
    • (2009) J. Med. Chem. , vol.52 , pp. 4883-4891
    • Chang, Y.H.1    Hsu, M.H.2    Wang, S.H.3    Huang, L.J.4    Qian, K.5    Morris-Natschke, S.L.6    Hamel, E.7    Kuo, S.C.8    Lee, K.H.9
  • 8
    • 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
    • DOI 10.1021/jm960858s
    • K. Chen, S.C. Kuo, M.C. Hsieh, A. Mauger, C.M. Lin, E. Hamel, and K.H. Lee 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. 40 1997 2266 2275 (Pubitemid 27284365)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.14 , 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
  • 9
    • 0030823308 scopus 로고    scopus 로고
    • Antitumor agents. 178. Synthesis and biological evaluation of substituted 2-aryl-1,8-naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization
    • DOI 10.1021/jm970146h
    • K. Chen, S.C. Kuo, M.C. Hsieh, A. Mauger, C.M. Lin, E. Hamel, and K.H. Lee Antitumor agents. 178. Synthesis and biological evaluation of substituted 2-Aryl-1,8-naphthyridin-4(1H)-ones as antitumor agents that inhibit tubulin polymerization J. Med. Chem. 40 1997 3049 3056 (Pubitemid 27391535)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.19 , 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
  • 10
    • 0033533865 scopus 로고    scopus 로고
    • Antitumor agents. 196. Substituted 2-thienyl-1,8-naphthyridin-4-ones: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization
    • DOI 10.1021/jm990208z
    • S.X. Zhang, K.F. Bastow, Y. Tachibana, S.C. Kuo, E. Hamel, A. Mauger, V.L. Narayanan, and K.H. Lee Antitumor agents. 196. Substituted 2-thienyl-1,8-naphthyridin-4-ones: their synthesis, cytotoxicity, and inhibition of tubulin polymerization J. Med. Chem. 42 1999 4081 4087 (Pubitemid 29483025)
    • (1999) Journal of Medicinal Chemistry , vol.42 , Issue.20 , 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
  • 12
    • 0034676319 scopus 로고    scopus 로고
    • 6-alkylamino- and 2,3-dihydro-3-methoxy-2-phenyl-4-quinazolinones and related compounds: Their synthesis, cytotoxicity, and inhibition of tubulin polymerization
    • DOI 10.1021/jm000151c
    • M.J. Hour, L.J. Huang, S.C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, and K.H. Lee 6-Alkylamino- and 2,3-dihydro-3'-methoxy-2-phenyl-4- quinazolinones and related compounds: their synthesis, cytotoxicity, and inhibition of tubulin polymerization J. Med. Chem. 43 2000 4479 4487 (Pubitemid 32046872)
    • (2000) Journal of Medicinal Chemistry , vol.43 , Issue.23 , pp. 4479-4487
    • Hour, M.-J.1    Huang, L.-J.2    Kuo, S.-C.3    Xia, Y.4    Bastow, K.5    Nakanishi, Y.6    Hamel, E.7    Lee, K.-H.8
  • 14
    • 78649500865 scopus 로고    scopus 로고
    • Design, synthesis, and preclinical evaluation of new 5,6-(or 6,7-)disubstituted-2-(fluorophenyl)quinolin-4-one derivatives as potent antitumor agents
    • L.C. Chou, M.T. Tsai, M.H. Hsu, S.H. Wang, T.D. Way, C.H. Huang, H.Y. Lin, K. Qian, Y. Dong, K.H. Lee, L.J. Huang, and S.C. Kuo Design, synthesis, and preclinical evaluation of new 5,6-(or 6,7-)disubstituted-2-(fluorophenyl) quinolin-4-one derivatives as potent antitumor agents J. Med. Chem. 53 2010 8047 8058
    • (2010) J. Med. Chem. , vol.53 , pp. 8047-8058
    • Chou, L.C.1    Tsai, M.T.2    Hsu, M.H.3    Wang, S.H.4    Way, T.D.5    Huang, C.H.6    Lin, H.Y.7    Qian, K.8    Dong, Y.9    Lee, K.H.10    Huang, L.J.11    Kuo, S.C.12
  • 16
    • 84981759540 scopus 로고
    • Synthese von α- und γ-oxychinolinen
    • R. Camps Synthese von α- und γ-oxychinolinen Chem. Ber. 32 1899 3228 3234
    • (1899) Chem. Ber. , vol.32 , pp. 3228-3234
    • Camps, R.1
  • 17
    • 80955125113 scopus 로고    scopus 로고
    • Camps quinolinol synthesis
    • J.J. Li, E.J. Corey, John Wiley & Sons, Inc. Hoboken, New Jersey
    • D.A. Pflum Camps quinolinol synthesis J.J. Li, E.J. Corey, Name Reactions in Heterocyclic Chemistry 2005 John Wiley & Sons, Inc. Hoboken, New Jersey 386 389
    • (2005) Name Reactions in Heterocyclic Chemistry , pp. 386-389
    • Pflum, D.A.1
  • 18
    • 35348846488 scopus 로고    scopus 로고
    • Sequential Cu-catalyzed amidation-base-mediated camps cyclization: A two-step synthesis of 2-aryl-4-quinolones from o-halophenones
    • DOI 10.1021/jo701384n
    • C.P. Jones, K.W. Anderson, and S.L. Buchwald Sequential Cu-catalyzed amidation-base-mediated camps cyclization: a two-step synthesis of 2-aryl-4-quinolones from o-halophenones J. Org. Chem. 72 2007 7968 7973 (Pubitemid 47582583)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.21 , pp. 7968-7973
    • Jones, C.P.1    Anderson, K.W.2    Buchwald, S.L.3
  • 19
    • 48849087952 scopus 로고    scopus 로고
    • A mild, one-pot synthesis of 4-quinolones via sequential Pd-catalyzed amidation and base-promoted cyclization
    • J. Huang, Y. Chen, A.O. King, M. Dilmeghani, R.D. Larsen, and M.M. Faul A mild, one-pot synthesis of 4-quinolones via sequential Pd-catalyzed amidation and base-promoted cyclization Org. Lett. 10 2008 2609 2612
    • (2008) Org. Lett. , vol.10 , pp. 2609-2612
    • Huang, J.1    Chen, Y.2    King, A.O.3    Dilmeghani, M.4    Larsen, R.D.5    Faul, M.M.6
  • 20
    • 33747780496 scopus 로고    scopus 로고
    • Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2-aminoacetophenones
    • DOI 10.1016/j.tetlet.2006.07.117, PII S0040403906015255
    • D. Ding, X. Li, X. Wang, Y. Du, and J. Shen Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2′-aminoacetophenones Tetrahedron Lett. 47 2006 6997 6999 (Pubitemid 44278966)
    • (2006) Tetrahedron Letters , vol.47 , Issue.39 , pp. 6997-6999
    • Ding, D.1    Li, X.2    Wang, X.3    Du, Y.4    Shen, J.5
  • 22
    • 0035525733 scopus 로고    scopus 로고
    • Cellular stress response and apoptosis in cancer therapy
    • I. Herr, and K.M. Debatin Cellular stress response and apoptosis in cancer therapy Blood 98 2001 2603 2614
    • (2001) Blood , vol.98 , pp. 2603-2614
    • Herr, I.1    Debatin, K.M.2
  • 23
    • 33947438568 scopus 로고
    • Metalation of thiophene by n-butyllithium
    • H. Gilman, and A. David Shirley Metalation of thiophene by n-butyllithium J. Am. Chem. Soc. 71 1949 1870 1871
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 1870-1871
    • Gilman, H.1    David Shirley, A.2
  • 24
    • 0001173379 scopus 로고
    • Oxidation of 2,4-alkadienoic esters with selenium dioxide: A new synthesis of furans and selenophenes
    • S. Tsuboi, S. Mimura, S.I. Ono, K. Watanabe, and A. Takeda Oxidation of 2,4-alkadienoic esters with selenium dioxide: a new synthesis of furans and selenophenes Bull. Chem. Soc. Jpn. 60 1987 1807 1812
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 1807-1812
    • Tsuboi, S.1    Mimura, S.2    Ono, S.I.3    Watanabe, K.4    Takeda, A.5
  • 26
    • 0029787938 scopus 로고    scopus 로고
    • Substituent effects on the lifetimes and reactivities of arylnitrenium ions studied by laser flash photolysis and photothermal beam deflection
    • DOI 10.1021/ja961518z
    • R.J. Robbins, D.M. Laman, and D.E. Falvey Substituent effects on the lifetimes and reactivities of arylnitrenium ions studied by laser flash photolysis and photothermal beam deflection J. Am. Chem. Soc. 118 1996 8127 8135 (Pubitemid 26305173)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.34 , pp. 8127-8135
    • Robbins, R.J.1    Laman, D.M.2    Falvey, D.E.3
  • 27
    • 19644369596 scopus 로고    scopus 로고
    • Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones
    • DOI 10.1248/cpb.53.547
    • H. Kagawa, A. Shigematsu, S. Ohta, and Y. Harigaya Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones Chem. Pharm. Bull. 53 2005 547 554 (Pubitemid 40740625)
    • (2005) Chemical and Pharmaceutical Bulletin , vol.53 , Issue.5 , pp. 547-554
    • Kagawa, H.1    Shigematsu, A.2    Ohta, S.3    Harigaya, Y.4
  • 28
    • 27644599576 scopus 로고    scopus 로고
    • 1-(3,4-Dimethoxyphenyl)-3,5-dodecenedione (I6) induces G1 arrest and apoptosis in human promyelocytic leukemia HL-60 cells
    • M.H. Hsu, S.C. Kuo, C.J. Chen, J.G. Chung, Y.Y. Lai, and L.J. Huang 1-(3,4-Dimethoxyphenyl)-3,5-dodecenedione (I6) induces G1 arrest and apoptosis in human promyelocytic leukemia HL-60 cells Leuk. Res. 29 2005 1399 1406
    • (2005) Leuk. Res. , vol.29 , pp. 1399-1406
    • Hsu, M.H.1    Kuo, S.C.2    Chen, C.J.3    Chung, J.G.4    Lai, Y.Y.5    Huang, L.J.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.