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Volumn 50, Issue 7, 2007, Pages 1707-1710

Quinols as novel therapeutic agents. 7. Synthesis of antitumor 4-[1-(arylsulfonyl-1H-indol-2-yl)]-4-hydroxycyclohexa-2,5-dien-1-ones by Sonogashira reactions

Author keywords

[No Author keywords available]

Indexed keywords

2 IODOANILINE; 4 (1 BENZENESULFONYL 6 FLUORO 1H INDOL 2 YL) 4 HYDROXYCYCLOHEXA 2,5 DIEN 1 ONE; 4 ETHYNYL 4 HYDROXYCYCLOHEXA 2,5 DIEN 1 ONE; 4 HYDROXYCYCLOHEXA 2,5 DIEN 1 ONE DERIVATIVE; ALKYNE DERIVATIVE; ANILINE DERIVATIVE; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; IODINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 34147180527     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061163m     Document Type: Article
Times cited : (48)

References (27)
  • 1
    • 33747507687 scopus 로고    scopus 로고
    • Antitumour properties of fluorinated benzothiazole- substituted hydroxycyclohexa-2,5-dienones("quinols")
    • Lion, C. J.; Matthews, C. S.; Bradshaw, T. D.; Wells, G.; Stevens, M. F. G.; Westwell. A. D. Antitumour properties of fluorinated benzothiazole- substituted hydroxycyclohexa-2,5-dienones("quinols"). Bioorg. Med. Chem. Lett. 2006, 16, 5005-5008.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 5005-5008
    • Lion, C.J.1    Matthews, C.S.2    Bradshaw, T.D.3    Wells, G.4    Stevens, M.F.G.5    Westwell, A.D.6
  • 2
    • 0037434507 scopus 로고    scopus 로고
    • 4-Substituted 4-hydroxycyclohexa-2, 5-dien-1-ones with selective activities against colon and renal cancer cell lines
    • Wells, G.; Berry, J. M.; Bradshaw, T. D.; Burger, A. M.; Seaton, A.; Wang, B.; Westwell, A. D.; Stevens, M. F. G. 4-Substituted 4-hydroxycyclohexa-2, 5-dien-1-ones with selective activities against colon and renal cancer cell lines. J. Med. Chem. 2003, 46, 532-541.
    • (2003) J. Med. Chem , vol.46 , pp. 532-541
    • Wells, G.1    Berry, J.M.2    Bradshaw, T.D.3    Burger, A.M.4    Seaton, A.5    Wang, B.6    Westwell, A.D.7    Stevens, M.F.G.8
  • 4
    • 33749318557 scopus 로고    scopus 로고
    • Novel thioredoxin inhibitors paradoxically increase hypoxia-inducible factor-α expression but decrease functional transcriptional activity, DNA binding, and degradation
    • Jones, D. T.; Pugh, C. W.; Wigfield, S.; Stevens, M. F. G.; Harris, A. L. Novel thioredoxin inhibitors paradoxically increase hypoxia-inducible factor-α expression but decrease functional transcriptional activity, DNA binding, and degradation. Clin. Cancer Res. 2006, 12, 5384-5394.
    • (2006) Clin. Cancer Res , vol.12 , pp. 5384-5394
    • Jones, D.T.1    Pugh, C.W.2    Wigfield, S.3    Stevens, M.F.G.4    Harris, A.L.5
  • 5
    • 14844293843 scopus 로고    scopus 로고
    • Cytotoxic and antiangiogenic activity of AW464 (NSC 706704), a novel thioredoxin inhibitor: An in vitro study
    • Mukherjee, A.; Westwell, A. D.; Bradshaw, T. D.; Stevens, M. F. G.; Carmichael, J.; Martin, S. G. Cytotoxic and antiangiogenic activity of AW464 (NSC 706704), a novel thioredoxin inhibitor: An in vitro study. Br. J. Cancer 2005, 92, 350-358.
    • (2005) Br. J. Cancer , vol.92 , pp. 350-358
    • Mukherjee, A.1    Westwell, A.D.2    Bradshaw, T.D.3    Stevens, M.F.G.4    Carmichael, J.5    Martin, S.G.6
  • 6
    • 12344254823 scopus 로고    scopus 로고
    • Quinols as novel therapeutic agents. 2. 4-(1-arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien- 1-ones and related agents as potent and selective antitumor agents
    • Berry, J. M.; Bradshaw, T. D.; Fichtner, I.; Ren, R. ; Schwalbe, C. H.; Wells, G.; Chew, E.-H.; Stevens, M. F. G.; Westwell, A. D. Quinols as novel therapeutic agents. 2. 4-(1-arylsulfonylindol-2-yl)-4-hydroxycyclohexa-2,5-dien- 1-ones and related agents as potent and selective antitumor agents. J. Med. Chem. 2005, 48, 639-644.
    • (2005) J. Med. Chem , vol.48 , pp. 639-644
    • Berry, J.M.1    Bradshaw, T.D.2    Fichtner, I.3    Ren, R.4    Schwalbe, C.H.5    Wells, G.6    Chew, E.-H.7    Stevens, M.F.G.8    Westwell, A.D.9
  • 7
    • 34147163533 scopus 로고    scopus 로고
    • Stevens, M. F. G.; Westwell, A. D.; Poole, T. D.; Wells, G.; Berry, J. M. 4-(1-(Sulfonyl)-1H-indol-2-yl)-4-(hydroxy)-cyclohexa-2,5-dienone compounds and analogs thereof as therapeutic agents. International Publication Number WO 2004/056361 A1, 2004.
    • Stevens, M. F. G.; Westwell, A. D.; Poole, T. D.; Wells, G.; Berry, J. M. 4-(1-(Sulfonyl)-1H-indol-2-yl)-4-(hydroxy)-cyclohexa-2,5-dienone compounds and analogs thereof as therapeutic agents. International Publication Number WO 2004/056361 A1, 2004.
  • 8
    • 0002082317 scopus 로고
    • Indoles, benzofurans, phthalides, and tolanes via copper(I) acetylides
    • Castro, C. E.; Gaughan, E. J.; Owsley, D. C. Indoles, benzofurans, phthalides, and tolanes via copper(I) acetylides. J. Org. Chem. 1966, 31, 4071-4078.
    • (1966) J. Org. Chem , vol.31 , pp. 4071-4078
    • Castro, C.E.1    Gaughan, E.J.2    Owsley, D.C.3
  • 9
    • 0000056092 scopus 로고
    • Thallium in organic synthesis. 68. A convenient synthesis of 2-phenylindoles from anilides
    • Taylor, E. C.; Katz, A. H.; Salgado-Zamora, H.; McKillop, A. Thallium in organic synthesis. 68. A convenient synthesis of 2-phenylindoles from anilides. Tetrahedron Lett. 1985, 26, 5963-5966.
    • (1985) Tetrahedron Lett , vol.26 , pp. 5963-5966
    • Taylor, E.C.1    Katz, A.H.2    Salgado-Zamora, H.3    McKillop, A.4
  • 10
    • 84952131058 scopus 로고
    • Condensed heteroaromatic ring-systems. 13. One-step synthesis of 2-substituted 1-methyl-sulfonylindoles from N-(2-halophenyl)-methanesulfonamides
    • Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.; Yamanaka, H. Condensed heteroaromatic ring-systems. 13. One-step synthesis of 2-substituted 1-methyl-sulfonylindoles from N-(2-halophenyl)-methanesulfonamides. Chem. Pharm. Bull. 1988, 36, 1305-1308.
    • (1988) Chem. Pharm. Bull , vol.36 , pp. 1305-1308
    • Sakamoto, T.1    Kondo, Y.2    Iwashita, S.3    Nagano, T.4    Yamanaka, H.5
  • 11
    • 22944454156 scopus 로고    scopus 로고
    • Synthesis and functionalization of indoles through palladium-catalyzed reactions
    • Cacchi, S.; Fabrizi, G. Synthesis and functionalization of indoles through palladium-catalyzed reactions. Chem. Rev. 2005, 105, 2873-2920.
    • (2005) Chem. Rev , vol.105 , pp. 2873-2920
    • Cacchi, S.1    Fabrizi, G.2
  • 12
    • 9244223861 scopus 로고    scopus 로고
    • Synthesis of five- and six-membered heterocycles through palladium-catalyzed reactions
    • Kirsch, G.; Hesse, S.; Cornel, A. Synthesis of five- and six-membered heterocycles through palladium-catalyzed reactions. Curr. Org. Synth. 2004, 1, 47-63.
    • (2004) Curr. Org. Synth , vol.1 , pp. 47-63
    • Kirsch, G.1    Hesse, S.2    Cornel, A.3
  • 13
    • 0036678797 scopus 로고    scopus 로고
    • The aminopalladation/reductive elimination domino reaction in the construction of functionalized indole rings
    • Battistuzzi, G.; Cacchi, S.; Fabrizi, G. The aminopalladation/reductive elimination domino reaction in the construction of functionalized indole rings. Eur. J. Org. Chem. 2002, 2671-2681.
    • (2002) Eur. J. Org. Chem , pp. 2671-2681
    • Battistuzzi, G.1    Cacchi, S.2    Fabrizi, G.3
  • 14
    • 0037159790 scopus 로고    scopus 로고
    • Nitrogen-containing heterocycles via palladium-catalyzed reaction of alkynes with organic halides or triflates
    • Cacchi, S.; Fabrizi, G.; Parisi, L. M. Nitrogen-containing heterocycles via palladium-catalyzed reaction of alkynes with organic halides or triflates. Heterocycles 2002, 58, 667-682.
    • (2002) Heterocycles , vol.58 , pp. 667-682
    • Cacchi, S.1    Fabrizi, G.2    Parisi, L.M.3
  • 15
    • 33846157379 scopus 로고    scopus 로고
    • Palladium-catalyzed annulation of alkynes
    • Larock, R. C. Palladium-catalyzed annulation of alkynes. Topics in Organometallic Chemistry 2005, 14, 147-182.
    • (2005) Topics in Organometallic Chemistry , vol.14 , pp. 147-182
    • Larock, R.C.1
  • 16
    • 0001075641 scopus 로고    scopus 로고
    • Palladium-catalyzed annulation
    • Larock, R. C. Palladium-catalyzed annulation. J. Organomet. Chem. 1999, 576, 111-124.
    • (1999) J. Organomet. Chem , vol.576 , pp. 111-124
    • Larock, R.C.1
  • 17
    • 0002214383 scopus 로고    scopus 로고
    • Facile solid-phase construction of indole derivatives based on a traceless, activating sulfonyl linker
    • Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.; Maryanoff, B. E. Facile solid-phase construction of indole derivatives based on a traceless, activating sulfonyl linker. Org. Lett. 2000, 2, 89-92.
    • (2000) Org. Lett , vol.2 , pp. 89-92
    • Zhang, H.-C.1    Ye, H.2    Moretto, A.F.3    Brumfield, K.K.4    Maryanoff, B.E.5
  • 18
    • 0035903909 scopus 로고    scopus 로고
    • Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted- benzo[b]furans and 2-substituted-indoles
    • Kabalka, G. W.; Wang, L.; Pagni, R. M. Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted- benzo[b]furans and 2-substituted-indoles. Tetrahedron 2001, 57, 8017-8028.
    • (2001) Tetrahedron , vol.57 , pp. 8017-8028
    • Kabalka, G.W.1    Wang, L.2    Pagni, R.M.3
  • 19
    • 2442455607 scopus 로고    scopus 로고
    • Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)
    • Suzuki, N.; Yasaki, S.; Yasuhara, A.; Sakamoto, T. Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF). Chem. Pharm. Bull. 2003, 51, 1170-1173.
    • (2003) Chem. Pharm. Bull , vol.51 , pp. 1170-1173
    • Suzuki, N.1    Yasaki, S.2    Yasuhara, A.3    Sakamoto, T.4
  • 20
    • 0344835674 scopus 로고    scopus 로고
    • Sonogashira coupling of aryl halides catalyzed by palladium on charcoal
    • Novak, Z.; Szabo, A.; Repasi, J.; Kotschy, A. Sonogashira coupling of aryl halides catalyzed by palladium on charcoal. J. Org. Chem. 2003, 68, 3327-3329.
    • (2003) J. Org. Chem , vol.68 , pp. 3327-3329
    • Novak, Z.1    Szabo, A.2    Repasi, J.3    Kotschy, A.4
  • 22
    • 0026571559 scopus 로고
    • Mixed quinone monoketals via iodobenzene diacetate oxidation
    • Fleck, A. E.; Hobart, J. A.; Morrow, G. W. Mixed quinone monoketals via iodobenzene diacetate oxidation. Synth. Commun. 1992, 22, 179-187.
    • (1992) Synth. Commun , vol.22 , pp. 179-187
    • Fleck, A.E.1    Hobart, J.A.2    Morrow, G.W.3
  • 23
    • 0035354662 scopus 로고    scopus 로고
    • New cyclohexadienone derivatives: Preparation and chiral discrimination in high-pressure Diels-Alder cycloadditions
    • Tran-Huu-Dau, M.-E.; Wartchow, R.; Winterfeldt, E.; Wong, Y. S. New cyclohexadienone derivatives: Preparation and chiral discrimination in high-pressure Diels-Alder cycloadditions. Chem. Eur. J. 2001, 7, 2349-2369.
    • (2001) Chem. Eur. J , vol.7 , pp. 2349-2369
    • Tran-Huu-Dau, M.-E.1    Wartchow, R.2    Winterfeldt, E.3    Wong, Y.S.4
  • 24
    • 14844299308 scopus 로고    scopus 로고
    • A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide
    • Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide. Angew. Chem., Int. Ed. 2005, 44, 1378-1382.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 1378-1382
    • Nicolaou, K.C.1    Estrada, A.A.2    Zak, M.3    Lee, S.H.4    Safina, B.S.5
  • 25
    • 0000616329 scopus 로고
    • Metalation/Srn1 coupling in heterocyclic synthesis-A convenient methodology for ring functionalization
    • Estel, L.; Marsais, F.; Queguiner, G. Metalation/Srn1 coupling in heterocyclic synthesis-A convenient methodology for ring functionalization. J. Org. Chem. 1988, 53, 2740-2744.
    • (1988) J. Org. Chem , vol.53 , pp. 2740-2744
    • Estel, L.1    Marsais, F.2    Queguiner, G.3
  • 26
    • 0343650986 scopus 로고    scopus 로고
    • Synthesis of new melatoninergic ligands including azaindole moiety
    • Mazeas, D.; Guillaumet, G.; Viaud, M.-C. Synthesis of new melatoninergic ligands including azaindole moiety. Heterocycles 1999, 50, 1065-1080.
    • (1999) Heterocycles , vol.50 , pp. 1065-1080
    • Mazeas, D.1    Guillaumet, G.2    Viaud, M.-C.3
  • 27
    • 0028906786 scopus 로고
    • Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen
    • Boyd, M. R.; Paull, 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    Paull, K.D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.