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Volumn 18, Issue 1, 2013, Pages 97-113

Synthesis and promising in Vitro antiproliferative activity of sulfones of a 5-nitrothiazole series

Author keywords

5 nitrothiazole; Activity cellular specificity; HepG2 cell line; In vitro antiproliferative; Microwave irradiation; Sulfones

Indexed keywords

5 NITROTHIAZOLE; 5-NITROTHIAZOLE; SULFONE; THIAZOLE DERIVATIVE;

EID: 84872837732     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18010097     Document Type: Article
Times cited : (13)

References (52)
  • 1
    • 80054850810 scopus 로고    scopus 로고
    • Macrocyclic proteasome inhibitors
    • Krahn, D.; Ottmann, C.; Kaiser, M. Macrocyclic proteasome inhibitors. Curr. Med. Chem. 2011, 18, 5052-5060.
    • (2011) Curr. Med. Chem. , vol.18 , pp. 5052-5060
    • Krahn, D.1    Ottmann, C.2    Kaiser, M.3
  • 3
    • 80054895057 scopus 로고    scopus 로고
    • Substituted phenyl-4-(2-oxoimidazolin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-Activity relationships
    • Fortin, S.; Wei, L.; Moreau, E.; Lacroix, J.; Côté, M.F.; Petitclerc, E.; Kotra, L.P.; Gaudreault, R.C. Substituted phenyl-4-(2- oxoimidazolin-1-yl)benzenesulfonamides as antimitotics. Antiproliferative, antiangiogenic and antitumoral activity, and quantitative structure-Activity relationships. Eur. J. Med. Chem. 2011, 46, 5327-5342.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 5327-5342
    • Fortin, S.1    Wei, L.2    Moreau, E.3    Lacroix, J.4    Côté, M.F.5    Petitclerc, E.6    Kotra, L.P.7    Gaudreault, R.C.8
  • 4
    • 78649444057 scopus 로고    scopus 로고
    • Design synthesis, and biological evaluation of novel n-carboline arylsulfonamides as anticancer agents
    • Chen, J.; Liu, T.; Wu, R.; Lou, J.; Cao, J.; Dong, X.; Yang, B.; He, Q.; Hu, Y. Design, synthesis, and biological evaluation of novel N-carboline arylsulfonamides as anticancer agents. Bioorg. Med. Chem. 2010, 18, 8478-8484.
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 8478-8484
    • Chen, J.1    Liu, T.2    Wu, R.3    Lou, J.4    Cao, J.5    Dong, X.6    Yang, B.7    He, Q.8    Hu, Y.9
  • 5
    • 79953702230 scopus 로고    scopus 로고
    • Antiproliferative effects of cox-2 inhibitor celecoxib on human breast cancer cell lines
    • Bocca, C.; Bozzo, F.; Bassignana, A.; Miglietta, A. Antiproliferative effects of COX-2 inhibitor celecoxib on human breast cancer cell lines. Mol. Cell. Biochem. 2011, 350, 59-70.
    • (2011) Mol. Cell. Biochem. , vol.350 , pp. 59-70
    • Bocca, C.1    Bozzo, F.2    Bassignana, A.3    Miglietta, A.4
  • 6
    • 80955151670 scopus 로고    scopus 로고
    • New imidazo [2,1-b]thiazoles derivatives: Synthesis, in vitro anticancer evaluation, and in silico studies
    • Park, J.H.; El-Gamal, M.I.; Lee, Y.S.; Oh, C.H. New imidazo[2,1-b] thiazoles derivatives: Synthesis, in vitro anticancer evaluation, and in silico studies. Eur. J. Med. Chem. 2011, 46, 5769-5777.
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 5769-5777
    • Park, J.H.1    El-Gamal, M.I.2    Lee, Y.S.3    Oh, C.H.4
  • 8
    • 0003497661 scopus 로고
    • 1st ed.; John Wiley and Sons: New York, NY, USA, and references therein.
    • Metzger, J.V. Thiazole and Its Derivatives, 1st ed.; John Wiley and Sons: New York, NY, USA, 1979, and references therein.
    • (1979) Thiazole Its Derivatives
    • Metzger, J.V.1
  • 10
    • 84872852744 scopus 로고
    • Cephalosporin derivatives and their pharmaceutical preparation
    • 058 250 filed 17 February , issued 25 August 1982
    • Angehrn, P.; Reiner, R. Cephalosporin derivatives and their pharmaceutical preparation. Eur. Patent 0,058,250, filed 17 February 1981, issued 25 August 1982
    • (1981) Eur. Patent 0
    • Angehrn, P.1    Reiner, R.2
  • 11
    • 84872838951 scopus 로고
    • Chem. Abstr. 1983, 98, 22269.
    • (1983) Chem. Abstr. , vol.98 , pp. 22269
  • 12
    • 0346101456 scopus 로고    scopus 로고
    • In vitro activities of the novel cephalosporin lb 11058 against multidrug-resistant staphylococci and streptococci
    • Sader, H.S.; Johnson, D.M.; Jones, R.N. In vitro activities of the novel cephalosporin LB 11058 against multidrug-resistant Staphylococci and Streptococci. Antimicrob. Agents Chemother. 2004, 48, 53-62.
    • (2004) Antimicrob. Agents Chemother. , vol.48 , pp. 53-62
    • Sader, H.S.1    Johnson, D.M.2    Jones, R.N.3
  • 13
    • 56049101851 scopus 로고    scopus 로고
    • Effects of febuxostat versus allopurinol and placebo in reducing serum urate in subjects with hyperuricemia and gout: A 28-week, phase iii, randomized, double-blind, parallel-group trial
    • Schumacher, H.R., Jr.; Becker, M.A.; Wortmann, R.L.; MacDonald, P.A.; Hunt, B.; Streit, J.; Lademacher, C.; Joseph-Ridge, N. Effects of febuxostat versus allopurinol and placebo in reducing serum urate in subjects with hyperuricemia and gout: A 28-week, phase III, randomized, double-blind, parallel-group trial. Arthritis Care Res. 2008, 59, 1540-1548.
    • (2008) Arthritis Care Res. , vol.59 , pp. 1540-1548
    • Schumacher Jr., H.R.1    Becker, M.A.2    Wortmann, R.L.3    MacDonald, P.A.4    Hunt, B.5    Streit, J.6    Lademacher, C.7    Joseph-Ridge, N.8
  • 15
    • 2942590820 scopus 로고    scopus 로고
    • Nitazoxanide: A new broad spectrum antiparasitic agent
    • White, A.C. Jr. Nitazoxanide: A new broad spectrum antiparasitic agent. Expert Rev. Anti-Infect. Ther. 2004, 2, 43-50.
    • (2004) Expert Rev. Anti-Infect. Ther. , vol.2 , pp. 43-50
    • White Jr., A.C.1
  • 19
    • 33644787638 scopus 로고    scopus 로고
    • Rapid syntheses of nitroheterocycles that bear a diethyl methylenemalonate group ß to a nitro group
    • Crozet, M.D.; Perfetti, P.; Kaafarani, M.; Crozet, M.P.; Vanelle, P. Rapid syntheses of nitroheterocycles that bear a diethyl methylenemalonate group ß to a nitro group. Lett. Org. Chem. 2004, 1, 326-330.
    • (2004) Lett. Org. Chem. , vol.1 , pp. 326-330
    • Crozet, M.D.1    Perfetti, P.2    Kaafarani, M.3    Crozet, M.P.4    Vanelle, P.5
  • 21
    • 50949121863 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity evaluation of some benzimidazole-47-diones as bioreductive anticancer agents
    • Gellis, A.; Kovacic, H.; Boufatah, N.; Vanelle, P. Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents. Eur. J. Med. Chem. 2008, 43, 1858-1864.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 1858-1864
    • Gellis, A.1    Kovacic, H.2    Boufatah, N.3    Vanelle, P.4
  • 23
    • 73949154689 scopus 로고    scopus 로고
    • Tdae-Assisted synthesis of new imidazo [2,1-b]thiazole derivatives as anti-infectious agents
    • Juspin, T.; Laget, M.; Terme, T.; Azas, N.; Vanelle, P. TDAE-Assisted synthesis of new imidazo[2,1-b]thiazole derivatives as anti-infectious agents. Eur. J. Med. Chem. 2010, 45, 840-845.
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 840-845
    • Juspin, T.1    Laget, M.2    Terme, T.3    Azas, N.4    Vanelle, P.5
  • 26
    • 0012720479 scopus 로고
    • Réactions srn1 en série hétérocycliques: Iv: Réactivité des sels du diméthyl-2,2 nitro-5 dioxanne-1,3
    • Crozet, M.P.; Archaimbault, G.; Vanelle, P.; Nouguier, R. Réactions SRN1 en série hétérocycliques: IV: Réactivité des sels du diméthyl-2,2 nitro-5 dioxanne-1,3. Tetrahedron Lett. 1985, 26, 5133-5134.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 5133-5134
    • Crozet, M.P.1    Archaimbault, G.2    Vanelle, P.3    Nouguier, R.4
  • 27
    • 81255179528 scopus 로고    scopus 로고
    • Long distance-srn1 in nitroimidazole series favored by temperature
    • Zink, L.; Crozet, M.D.; Terme, T.; Vanelle, P. Long distance-SRN1 in nitroimidazole series favored by temperature. Tetrahedron Lett. 2011, 52, 6991-6996.
    • (2011) Tetrahedron Lett. , vol.52 , pp. 6991-6996
    • Zink, L.1    Crozet, M.D.2    Terme, T.3    Vanelle, P.4
  • 28
    • 70449560855 scopus 로고    scopus 로고
    • Efficient microwave-Assisted palladium-catalyzed suzuki-miyaura cross-coupling reactions in 5-nitroimidazole series
    • Crozet, M.D.; Zink, L.; Remusat, V.; Curti, C.; Vanelle, P. Efficient microwave-Assisted palladium-catalyzed Suzuki-Miyaura cross-coupling reactions in 5-nitroimidazole series. Synthesis 2009, 3150-3156.
    • (2009) Synthesis , pp. 3150-3156
    • Crozet, M.D.1    Zink, L.2    Remusat, V.3    Curti, C.4    Vanelle, P.5
  • 29
    • 77952840496 scopus 로고    scopus 로고
    • Regioselective suzuki-miyaura reaction: Application to the microwave-promoted synthesis of 4,7-diarylquinazolines
    • Kabri, Y.; Verhaeghe, P.; Gellis, A.; Vanelle, P. Regioselective Suzuki-Miyaura reaction: Application to the microwave-promoted synthesis of 4,7-diarylquinazolines. Molecules 2010, 15, 2949-2961.
    • (2010) Molecules , vol.15 , pp. 2949-2961
    • Kabri, Y.1    Verhaeghe, P.2    Gellis, A.3    Vanelle, P.4
  • 30
    • 33747800721 scopus 로고    scopus 로고
    • An efficient microwave-Assisted suzuki cross-coupling reaction of imidazo [1,2-A]pyridines in aqueous medium
    • Crozet, M.D.; Castera-Ducros, C.; Vanelle, P. An efficient microwave-Assisted Suzuki cross-coupling reaction of imidazo[1,2-A]pyridines in aqueous medium. Tetrahedron Lett. 2006, 47, 7061-7065.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 7061-7065
    • Crozet, M.D.1    Castera-Ducros, C.2    Vanelle, P.3
  • 31
    • 70449334566 scopus 로고    scopus 로고
    • An efficient aqueous microwave-Assisted suzuki-miyaura cross-coupling reaction in the thiazole series
    • Cohen, A.; Crozet, M.D.; Rathelot, P.; Vanelle, P. An efficient aqueous microwave-Assisted Suzuki-Miyaura cross-coupling reaction in the thiazole series. Green Chem. 2009, 11, 1736-1742.
    • (2009) Green Chem. , vol.11 , pp. 1736-1742
    • Cohen, A.1    Crozet, M.D.2    Rathelot, P.3    Vanelle, P.4
  • 32
    • 0001655146 scopus 로고
    • The polymerization of 2-methyl-4-chloromethylthiazole
    • Hooper, F.E.; Johnson, T.B. The polymerization of 2-methyl-4- chloromethylthiazole. J. Am. Chem. Soc. 1934, 56, 470-471.
    • (1934) J. Am. Chem. Soc. , vol.56 , pp. 470-471
    • Hooper, F.E.1    Johnson, T.B.2
  • 36
    • 34447097175 scopus 로고    scopus 로고
    • Microwave-Assisted synthesis in water as solvent
    • Dallinger, D.; Kappe, C.O. Microwave-Assisted synthesis in water as solvent. Chem. Rev. 2007, 107, 2563-2591.
    • (2007) Chem. Rev. , vol.107 , pp. 2563-2591
    • Dallinger, D.1    Kappe, C.O.2
  • 37
    • 37549015931 scopus 로고    scopus 로고
    • Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry
    • Herrero, M.A.; Kremsner, J.M.; Kappe, C.O. Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry. J. Org. Chem. 2008, 73, 36-47.
    • (2008) J. Org. Chem. , vol.73 , pp. 36-47
    • Herrero, M.A.1    Kremsner, J.M.2    Kappe, C.O.3
  • 38
    • 47749088679 scopus 로고    scopus 로고
    • Aqueous microwave chemistry: A clean and green synthetic tool for rapid drug discovery
    • Polshettiwar, V.; Varma, R.S. Aqueous microwave chemistry: A clean and green synthetic tool for rapid drug discovery. Chem. Soc. Rev. 2008, 37, 1546-1557.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1546-1557
    • Polshettiwar, V.1    Varma, R.S.2
  • 39
    • 0004252595 scopus 로고    scopus 로고
    • 1st ed.; Blackie Academic and Professional: London, UK
    • Grieco, P.A. Organic Synthesis in Water, 1st ed.; Blackie Academic and Professional: London, UK, 1998.
    • (1998) Organic Synthesis in Water
    • Grieco, P.A.1
  • 43
    • 33646568471 scopus 로고    scopus 로고
    • Rapid microwave-promoted synthesis of new sulfonylmethylbenzothiazoles in water
    • Gellis, A.; Boufatah, N.; Vanelle, P. Rapid microwave-promoted synthesis of new sulfonylmethylbenzothiazoles in water. Green Chem. 2006, 8, 483-487.
    • (2006) Green Chem. , vol.8 , pp. 483-487
    • Gellis, A.1    Boufatah, N.2    Vanelle, P.3
  • 44
    • 33845397686 scopus 로고    scopus 로고
    • Microwave-Assisted solvent-free synthesis of substituted 2-quinolones
    • Jia, C.-S.; Dong, Y.-W.; Tu, S.-J.; Wang, G.-W. Microwave-Assisted solvent-free synthesis of substituted 2-quinolones. Tetrahedron 2007, 63, 892-897.
    • (2007) Tetrahedron , vol.63 , pp. 892-897
    • Jia, C.-S.1    Dong, Y.-W.2    Tu, S.-J.3    Wang, G.-W.4
  • 45
    • 68349088939 scopus 로고    scopus 로고
    • Synthesis of original 2-substituted 4-Arylquinazolines (iii) by microwave-irradiated suzuki-miyaura cross-coupling reactions
    • Kabri, Y.; Gellis, A.; Vanelle, P. Synthesis of original 2-substituted 4-Arylquinazolines (III) by microwave-irradiated Suzuki-Miyaura cross-coupling reactions. Eur. J. Org. Chem. 2009, 24, 4059-4066.
    • (2009) Eur. J. Org. Chem. , vol.24 , pp. 4059-4066
    • Kabri, Y.1    Gellis, A.2    Vanelle, P.3
  • 46
    • 34249285483 scopus 로고    scopus 로고
    • Rapid synthesis of sulfone derivatives as potential anti-infectious agents
    • Curti, C.; Laget, M.; Ortiz Carle, A.; Gellis, A.; Vanelle, P. Rapid synthesis of sulfone derivatives as potential anti-infectious agents. Eur. J. Med. Chem. 2007, 42, 880-884.
    • (2007) Eur. J. Med. Chem. , vol.42 , pp. 880-884
    • Curti, C.1    Laget, M.2    Ortiz Carle, A.3    Gellis, A.4    Vanelle, P.5
  • 47
    • 0242426997 scopus 로고
    • Methyl p-tolyl sulfone
    • Field, L.; Clark, R.D. Methyl p-tolyl sulfone. Org. Synth. 1958, 38, 62-65.
    • (1958) Org. Synth. , vol.38 , pp. 62-65
    • Field, L.1    Clark, R.D.2
  • 48
    • 3543068272 scopus 로고    scopus 로고
    • Chloromethyl sulfones from sulfonyl chlorides via a one-pot procedure
    • Antane, S.; Bernotas, R.; Li, Y.; McDevitt, R.; Yan, Y. Chloromethyl sulfones from sulfonyl chlorides via a one-pot procedure. Synth. Commun. 2004, 34, 2443-2449.
    • (2004) Synth. Commun. , vol.34 , pp. 2443-2449
    • Antane, S.1    Bernotas, R.2    Li, Y.3    McDevitt, R.4    Yan, Y.5
  • 49
    • 0000196929 scopus 로고
    • Copper-catalyzed additions of sulfonyl iodides to simple and cyclic alkenes
    • Liu, L.K.; Chi, Y.; Jen, K. Copper-catalyzed additions of sulfonyl iodides to simple and cyclic alkenes. J. Org. Chem. 1980, 45, 406-410.
    • (1980) J. Org. Chem. , vol.45 , pp. 406-410
    • Liu, L.K.1    Chi, Y.2    Jen, K.3
  • 50
    • 2542635138 scopus 로고    scopus 로고
    • Rapid side-chain chlorination of heterocyclic compounds using focused microwave irradiation
    • Kidwai, M.; Kohli, S.; Kumar, P. Rapid side-chain chlorination of heterocyclic compounds using focused microwave irradiation. J. Chem. Res. 1998, 586-587.
    • (1998) J. Chem. Res. , pp. 586-587
    • Kidwai, M.1    Kohli, S.2    Kumar, P.3
  • 51
    • 0021061819 scopus 로고
    • Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays
    • Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 52
    • 0036301269 scopus 로고    scopus 로고
    • Cytochrome p450 expression in human hepatocytes and hepatoma cell lines: Molecular mechanisms that determine lower expression in cultured cells
    • Rodriguez-Antona, C.; Donato, M.T.; Boobis, A.; Edwards, R.J.; Watts, P.S.; Castell, J.V.; Gómez-Lechón, M.J. Cytochrome P450 expression in human hepatocytes and hepatoma cell lines: Molecular mechanisms that determine lower expression in cultured cells. Xenobiotica 2002, 32, 505-520.
    • (2002) Xenobiotica , vol.32 , pp. 505-520
    • Rodriguez-Antona, C.1    Donato, M.T.2    Boobis, A.3    Edwards, R.J.4    Watts, P.S.5    Castell, J.V.6    Gómez-Lechón, M.J.7


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