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Volumn 83, Issue , 2014, Pages 389-397

Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: Syntheses, structures and biological evaluation

Author keywords

Alkynes; Antitumor agents; Boron neutron capture therapy; Carboranes; Drug research

Indexed keywords

ALPHA CARBORANYL DEOXYRIBOSIDE; ANTINEOPLASTIC AGENT; BETA CARBORANYL DEOXYRIBOSIDE; DEOXYRIBOSE; UNCLASSIFIED DRUG; BORON DERIVATIVE; NUCLEOSIDE; WATER; 2 (HYDROXYMETHYL) 5 (2 PHENYL DICARBA CLOSO DODECABORAN 1 YL)TETRAHYDRO FURAN 3 OL; 2 (HYDROXYMETHYL) 5 (DICARBA CLOSO DODECABORAN 1 YL)TETRAHYDROFURAN 3 OL; 2 (HYDROXYMETHYL) 5 [2 (2 PHENYL DICARBA CLOSODODECABORAN 1 YL) DICARBA CLOSO DODECABORON 1 YL] TETRAHYDROFURAN 3 OL; 2 (TOLUOYLOXYMETHYL) 3 TOLUOYLOXY 5 (2 PHENYLDICARBA CLOSO DODECABORAN 1 YL)TETRAHYDROFURAN; 2 (TOLUOYLOXYMETHYL) 3 TOLUOYLOXY 5 (DICARBACLOSO DODECABORAN 1 YL)TETRA HYDROFURAN; 2 (TOLUOYLOXYMETHYL) 3 TOLUOYLOXY 5 [2 (2 PHENYLDICARBA CLOSO DODECABO RAN 1 YL) DICARBA CLOSO DODECABORAN 1 YL]TETRAHYDROFURAN; 5 PHENYLETHYNYL 2 (TOLUOYLOXYMETHYL) 3 TOLUOYLOXYTETRAHYDROFURAN; 5 [(4 PHENYLETHYNYL)PHENYLETHYNYL] 2 (TOLUOYLOXYMETHYL) 3 TOLUOYLOXYTETRA HYDROFURAN; 7 [2 [(HYDROXYMETHYL) 3 HYDROXY TETRAHYDROFURAN 5 YL]] 7,8 DICARBA NIDO UNDECARBONATE; CARBORANE DERIVATIVE;

EID: 84903609015     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.005     Document Type: Article
Times cited : (11)

References (35)
  • 1
    • 12444279265 scopus 로고
    • Origin of cancer cells
    • O. Warburg Origin of cancer cells Science 123 1956 309 314
    • (1956) Science , vol.123 , pp. 309-314
    • Warburg, O.1
  • 2
    • 33749478922 scopus 로고    scopus 로고
    • Cancer's molecular sweet tooth and the warburg effect
    • DOI 10.1158/0008-5472.CAN-06-1501
    • J.-W. Kim, and C.V. Dang Cancer's molecular sweet tooth and the Warburg effect Cancer Res. 66 2006 8927 8930 (Pubitemid 44521105)
    • (2006) Cancer Research , vol.66 , Issue.18 , pp. 8927-8930
    • Kim, J.-W.1    Dang, C.V.2
  • 3
    • 0000857737 scopus 로고
    • Potential application of the boron cluster compounds
    • J. Plešek Potential application of the boron cluster compounds Chem. Rev. 92 1992 269 278
    • (1992) Chem. Rev. , vol.92 , pp. 269-278
    • Plešek, J.1
  • 4
    • 65349140600 scopus 로고    scopus 로고
    • Polyhedral boranes for medical applications: Current status and perspectives
    • I.B. Sivaev, and V.V. Bregadze Polyhedral boranes for medical applications: current status and perspectives Eur. J. Org. Chem. 2009 1433 1450
    • (2009) Eur. J. Org. Chem. , pp. 1433-1450
    • Sivaev, I.B.1    Bregadze, V.V.2
  • 7
    • 0000229150 scopus 로고    scopus 로고
    • Applications of Radiolabeled Boron Clusters to the Diagnosis and Treatment of Cancer
    • M.F. Hawthorne, and A. Maderna Applications of radiolabeled boron clusters to the diagnosis and treatment of cancer Chem. Rev. 99 1999 3421 3434 (Pubitemid 129589124)
    • (1999) Chemical Reviews , vol.99 , Issue.12 , pp. 3421-3434
    • Hawthorne, M.F.1    Maderna, A.2
  • 8
    • 20344394447 scopus 로고    scopus 로고
    • Boron neutron capture therapy of cancer: Current status and future prospects
    • DOI 10.1158/1078-0432.CCR-05-0035
    • R.F. Barth, J.A. Coderre, M.G. Vincente, and T.E. Blue Boron neutron capture therapy of cancer: current status and future prospects Clin. Cancer Res. 11 2005 3987 4002 (Pubitemid 40791562)
    • (2005) Clinical Cancer Research , vol.11 , Issue.11 , pp. 3987-4002
    • Barth, R.F.1    Coderre, J.A.2    Vicente, M.G.H.3    Blue, T.E.4
  • 12
    • 80755152419 scopus 로고    scopus 로고
    • Carbaboranes as pharmacophores: Properties, synthesis, and application strategies
    • M. Scholz, and E. Hey-Hawkins Carbaboranes as pharmacophores: properties, synthesis, and application strategies Chem. Rev. 111 2011 7035 7062
    • (2011) Chem. Rev. , vol.111 , pp. 7035-7062
    • Scholz, M.1    Hey-Hawkins, E.2
  • 13
    • 0026661314 scopus 로고
    • Synthesis and invitro evaluation of boronated uridine and glucose derivatives for boron neutron-capture therapy
    • W. Tjarks, A.K.M. Anisuzzaman, L. Liu, A.H. Soloway, R.F. Barth, D.J. Perkins, and D.M. Adams Synthesis and invitro evaluation of boronated uridine and glucose derivatives for boron neutron-capture therapy J. Med. Chem. 35 1992 1628 1633
    • (1992) J. Med. Chem. , vol.35 , pp. 1628-1633
    • Tjarks, W.1    Anisuzzaman, A.K.M.2    Liu, L.3    Soloway, A.H.4    Barth, R.F.5    Perkins, D.J.6    Adams, D.M.7
  • 15
    • 0031876367 scopus 로고    scopus 로고
    • Ortho-carboranyl glycosides of glucose, mannose, maltose and lactose for cancer treatment by boron neutron-capture therapy
    • DOI 10.1002/(SICI)1521-3765(19980710)4:7<1179::AID-CHEM1179>3.0. CO;2-F
    • L.F. Tietze, and U. Bothe Ortho-carboranyl glycosides of glucose, mannose, maltose and lactose for cancer treatment by boron neutron-capture therapy Chem. Eur. J. 4 1998 1179 1183 (Pubitemid 28370057)
    • (1998) Chemistry - A European Journal , vol.4 , Issue.7 , pp. 1179-1183
    • Tietze, L.F.1    Bothe, U.2
  • 16
    • 0033521104 scopus 로고    scopus 로고
    • Synthesis of carboranyl derivatives of alkynyl glycosides as potential BNCT agents
    • G.B. Giovenzana, L. Lay, D. Monti, G. Palmisano, and L. Panza Synthesis of carboranyl derivatives of alkynyl glycosides as potential BNCT agents Tetrahedron 55 1999 14123 14136
    • (1999) Tetrahedron , vol.55 , pp. 14123-14136
    • Giovenzana, G.B.1    Lay, L.2    Monti, D.3    Palmisano, G.4    Panza, L.5
  • 17
  • 18
    • 12344269806 scopus 로고    scopus 로고
    • Synthesis of mono- and bisglucuronylated carboranes
    • DOI 10.1016/j.tetasy.2004.11.059, PII S0957416604009073
    • S. Ronchi, D. Prosperi, C. Thimon, C. Morin, and L. Panza Synthesis of mono- and bisglucuronylated carboranes Tetrahedron Asym. 16 2005 39 44 (Pubitemid 40127073)
    • (2005) Tetrahedron Asymmetry , vol.16 , Issue.1 , pp. 39-44
    • Ronchi, S.1    Prosperi, D.2    Thimon, C.3    Morin, C.4    Panza, L.5
  • 19
    • 84855206162 scopus 로고    scopus 로고
    • Synthesis of complex glycosylated carboranes for BNCT
    • F. Campo, M. Mossotti, and L. Panya Synthesis of complex glycosylated carboranes for BNCT Synlett 2012 120 122
    • (2012) Synlett , pp. 120-122
    • Campo, F.1    Mossotti, M.2    Panya, L.3
  • 21
    • 77952626256 scopus 로고    scopus 로고
    • Bis-carbaborane-bridged bis-glycophosphonates as boron-rich delivery agents for BNCT
    • S. Stadlbauer, P. Lönnecke, P. Welzel, and E. Hey-Hawkins Bis-carbaborane-bridged bis-glycophosphonates as boron-rich delivery agents for BNCT Eur. J. Org. Chem. 2010 3129 3139
    • (2010) Eur. J. Org. Chem. , pp. 3129-3139
    • Stadlbauer, S.1    Lönnecke, P.2    Welzel, P.3    Hey-Hawkins, E.4
  • 22
    • 70350632652 scopus 로고    scopus 로고
    • Synthesis of conjugates of polyhedral boron compounds with carbohydrates
    • For a review, see
    • For a review, see A.V. Orlova, and L.O. Kononov Synthesis of conjugates of polyhedral boron compounds with carbohydrates Russ. Chem. Rev. 78 2009 629 642
    • (2009) Russ. Chem. Rev. , vol.78 , pp. 629-642
    • Orlova, A.V.1    Kononov, L.O.2
  • 23
    • 0037451465 scopus 로고    scopus 로고
    • Novel carboranyl C-glycosides for the treatment of cancer by boron neutron capture therapy
    • L.F. Tietze, U. Griesbach, I. Schuberth, U. Bothe, A. Marra, and A. Dondoni Novel carboranyl C-glycosides for the treatment of cancer by boron neutron capture therapy Chem. Eur. J. 9 2003 1296 1302
    • (2003) Chem. Eur. J. , vol.9 , pp. 1296-1302
    • Tietze, L.F.1    Griesbach, U.2    Schuberth, I.3    Bothe, U.4    Marra, A.5    Dondoni, A.6
  • 24
    • 3242694439 scopus 로고    scopus 로고
    • Synthesis and cycloaddition reactions of [2-deoxy-3,5-bis[O-(p-toluoyl)]- alpha-D-ribofuranosyl]ethyne
    • H. Wamhoff, and H. Warnecke Synthesis and cycloaddition reactions of [2-deoxy-3,5-bis[O-(p-toluoyl)]-alpha-D-ribofuranosyl]ethyne ARKIVOC 2001 95 100
    • (2001) ARKIVOC , pp. 95-100
    • Wamhoff, H.1    Warnecke, H.2
  • 25
    • 33744758315 scopus 로고    scopus 로고
    • Synthesis of C-aryldeoxyribosides by [2 + 2 + 2]-cyclotrimerization catalyzed by Rh, Ni, Co, and Ru complexes
    • DOI 10.1021/ol060454m
    • P. Novák, R. Pohl, M. Hocek, and M. Kotora Synthesis of C-aryldeoxyribosides by [2+2+2]-cyclotrimerization catalyzed by Rh, Ni, Co, and Ru complexes Org. Lett. 8 2006 2051 2054 (Pubitemid 43823608)
    • (2006) Organic Letters , vol.8 , Issue.10 , pp. 2051-2054
    • Novak, P.1    Pohl, R.2    Kotora, M.3    Hocek, M.4
  • 26
    • 42749089143 scopus 로고    scopus 로고
    • Co- and homocyclotrimerization reactions of protected 1-alkynyl-2-deoxyribofuranose. Synthesis of C-nucleosides, C-di- and C-trisaccharide analogues
    • P. Novák, S. Číhalová, M. Otmar, M. Hocek, and M. Kotora Co- and homocyclotrimerization reactions of protected 1-alkynyl-2-deoxyribofuranose. Synthesis of C-nucleosides, C-di- and C-trisaccharide analogues Tetrahedron 64 2008 5200 5207
    • (2008) Tetrahedron , vol.64 , pp. 5200-5207
    • Novák, P.1    Číhalová, S.2    Otmar, M.3    Hocek, M.4    Kotora, M.5
  • 27
    • 56249108704 scopus 로고    scopus 로고
    • Extension of the library of biologically active gamma-alkylidene butenolides
    • P. Novák, M. Pour, M. Špulák, I. Votruba, and M. Kotora Extension of the library of biologically active gamma-alkylidene butenolides Synthesis 2008 3465 3472
    • (2008) Synthesis , pp. 3465-3472
    • Novák, P.1    Pour, M.2    Špulák, M.3    Votruba, I.4    Kotora, M.5
  • 28
    • 71049146778 scopus 로고    scopus 로고
    • Sonogashira reactions of alpha- and beta-1-ethynyl-2-deoxyribosides: Synthesis of acetylene-extended C-nucleosides
    • T. Bobula, M. Hocek, and M. Kotora Sonogashira reactions of alpha- and beta-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides Tetrahedron 66 2010 530 536
    • (2010) Tetrahedron , vol.66 , pp. 530-536
    • Bobula, T.1    Hocek, M.2    Kotora, M.3
  • 30
    • 0000210402 scopus 로고
    • Carboranes. I. The preparation and chemistry of 1-isopropenylcarborane and its derivatives (a new family of stable clovoboranes)
    • M.M. Fein, J. Bobinski, N. Mayes, N. Schwartz, and M.S. Cohen Carboranes. I. The preparation and chemistry of 1-isopropenylcarborane and its derivatives (a new family of stable clovoboranes) Inorg. Chem. 2 1963 1111 1115
    • (1963) Inorg. Chem. , vol.2 , pp. 1111-1115
    • Fein, M.M.1    Bobinski, J.2    Mayes, N.3    Schwartz, N.4    Cohen, M.S.5
  • 32
    • 3242739063 scopus 로고    scopus 로고
    • Polyborane reactions in ionic liquids: New efficient routes to functionalized decaborane and o-carborane clusters
    • DOI 10.1021/ja048018n
    • U. Kusari, Y. Li, M.G. Bradley, and L.G. Sneddon Polyborane reactions in ionic liquids: new efficient routes to functionalized decaborane and o-carborane clusters J. Am. Chem. Soc. 126 2004 8662 8663 (Pubitemid 38955725)
    • (2004) Journal of the American Chemical Society , vol.126 , Issue.28 , pp. 8662-8663
    • Kusari, U.1    Li, Y.2    Bradley, M.G.3    Sneddon, L.G.4
  • 33
    • 0035966680 scopus 로고    scopus 로고
    • Facile and mild deboronation of o-carboranes using cesium fluoride
    • DOI 10.1021/ic000768k
    • J. Yoo, J. Hwang, and Y. Do Facile and mild deboronation of o-carboranes using cesium fluoride Inorg. Chem. 40 2001 568 570 (Pubitemid 33064954)
    • (2001) Inorganic Chemistry , vol.40 , Issue.3 , pp. 568-570
    • Yoo, J.1    Hwang, J.-W.2    Do, Y.3
  • 34
    • 33644541767 scopus 로고    scopus 로고
    • Ruthenium-catalyzed homo and cross metathesis reactions of alkenylpolyboranes: New routes to functional o-carborane and decaborane derivatives
    • X. Wei, P.J. Carroll, and L.G. Sneddon Ruthenium-catalyzed homo and cross metathesis reactions of alkenylpolyboranes: new routes to functional o-carborane and decaborane derivatives Organometallics 25 2006 609 621
    • (2006) Organometallics , vol.25 , pp. 609-621
    • Wei, X.1    Carroll, P.J.2    Sneddon, L.G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.