메뉴 건너뛰기




Volumn , Issue , 2005, Pages 453-491

From natural to rationally designed artificial enediynes: Towards new anticancer antibiotics activable at will

Author keywords

[No Author keywords available]

Indexed keywords


EID: 34548325048     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter
Times cited : (3)

References (132)
  • 1
    • 0026045597 scopus 로고
    • Chemistry and biology of the enediyne anticancer antibiotics
    • Nicolaou, K. C. Chemistry and biology of the enediyne anticancer antibiotics. Angew. Chem., Int. Ed. Engl. 1991, 32, 1387-1416.
    • (1991) Angew. Chem., Int. Ed. Engl , vol.32 , pp. 1387-1416
    • Nicolaou, K.C.1
  • 2
    • 0030003961 scopus 로고    scopus 로고
    • The enediyne antibiotics
    • Smith, A.L.; Nicolaou, K.C. The enediyne antibiotics. J. Med. Chem. 1996, 39, 2103-2117.
    • (1996) J. Med. Chem , vol.39 , pp. 2103-2117
    • Smith, A.L.1    Nicolaou, K.C.2
  • 3
    • 0021960376 scopus 로고
    • The structure of neocarzinostatin chromophore possessing a novel bicyclo-[7,3,0]dodecadiyne system
    • Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. The structure of neocarzinostatin chromophore possessing a novel bicyclo-[7,3,0]dodecadiyne system. Tetrahedron Lett. 1985, 26, 331-340.
    • (1985) Tetrahedron Lett , vol.26 , pp. 331-340
    • Edo, K.1    Mizugaki, M.2    Koide, Y.3    Seto, H.4    Furihata, K.5    Otake, N.6    Ishida, N.7
  • 4
    • 0033673757 scopus 로고    scopus 로고
    • Understanding and exploiting nature's chemical arsenal: The past, present and future of calicheamicin research
    • Thorson, J.S.; Sievers, E.L.; Ahlert, J.; Shepard, E.; Whitwam, R.E.; Onwueme, K.C.; Ruppen, M. Understanding and exploiting nature's chemical arsenal: the past, present and future of calicheamicin research. Curr. Pharm. Design 2000, 6, 1841-1879.
    • (2000) Curr. Pharm. Design , vol.6 , pp. 1841-1879
    • Thorson, J.S.1    Sievers, E.L.2    Ahlert, J.3    Shepard, E.4    Whitwam, R.E.5    Onwueme, K.C.6    Ruppen, M.7
  • 6
    • 1642278107 scopus 로고    scopus 로고
    • Convergent approach to the maduropeptin chromophore: Aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam
    • Kato, N.; Shimamura, S.; Khan, S.; Takeda, F.; Kikai, Y.; Hirama, M. Convergent approach to the maduropeptin chromophore: aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam. Tetrahedron 2004, 60, 3161-3172.
    • (2004) Tetrahedron , vol.60 , pp. 3161-3172
    • Kato, N.1    Shimamura, S.2    Khan, S.3    Takeda, F.4    Kikai, Y.5    Hirama, M.6
  • 7
    • 0038392581 scopus 로고    scopus 로고
    • Non-caspase-mediated apoptosis contributes to the potent cytotoxicity of the enediyne antibiotic lidamycin toward human tumor cells
    • Wang, Z.; He, Q.Y.; Liang, Y.Y.; Wang, D.S.; Li, Y.Y.; Li, D.D. Non-caspase-mediated apoptosis contributes to the potent cytotoxicity of the enediyne antibiotic lidamycin toward human tumor cells. Biochem. Pharmacol. 2003, 65, 1767-1775.
    • (2003) Biochem. Pharmacol , vol.65 , pp. 1767-1775
    • Wang, Z.1    He, Q.Y.2    Liang, Y.Y.3    Wang, D.S.4    Li, Y.Y.5    Li, D.D.6
  • 8
    • 0036570339 scopus 로고    scopus 로고
    • Evidence for facile atropisomerism and simple (non-nucleophilic) biradical-forming cycloaromatization within kedarcidin chromophore aglycon
    • Myers, A.G.; Hurd, A.R.; Hogan, P.C. Evidence for facile atropisomerism and simple (non-nucleophilic) biradical-forming cycloaromatization within kedarcidin chromophore aglycon. J. Am. Chem. Soc. 2002, 124, 4583-4585.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 4583-4585
    • Myers, A.G.1    Hurd, A.R.2    Hogan, P.C.3
  • 9
    • 1642576273 scopus 로고    scopus 로고
    • Stereochemical control of small molecule binding to bulged DNA: Comparison of structures of spiro-cyclic enantiomer-bulged DNA complexes
    • Hwang, G.S.; Jones, G.B.; Goldberg, I.H. Stereochemical control of small molecule binding to bulged DNA: Comparison of structures of spiro-cyclic enantiomer-bulged DNA complexes. Biochemistry 2004, 43, 641-650
    • (2004) Biochemistry , vol.43 , pp. 641-650
    • Hwang, G.S.1    Jones, G.B.2    Goldberg, I.H.3
  • 10
    • 0037093875 scopus 로고    scopus 로고
    • Development of an enantio-selective synthetic route to neocarzinostatin chromophore and its use for multiple radioisotopic incorporation
    • Myers, A.G.; Glatthar, R.; Hammond, M.; Harrington, P.M.; Kuo, E.Y.; Liang, J.; Schaus, S.E.; Wu, Y.S.; Xiang, J.N. Development of an enantio-selective synthetic route to neocarzinostatin chromophore and its use for multiple radioisotopic incorporation. J. Am. Chem. Soc. 2002, 124, 5380-5401.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 5380-5401
    • Myers, A.G.1    Glatthar, R.2    Hammond, M.3    Harrington, P.M.4    Kuo, E.Y.5    Liang, J.6    Schaus, S.E.7    Wu, Y.S.8    Xiang, J.N.9
  • 12
    • 0037436944 scopus 로고    scopus 로고
    • Asymmetric synthesis of the cyclopentanones related to NCS and N1999A2 antitumor antibiotics
    • Bertus, P.; Zhang, J.H.; Sir, G.; Weibel, J.M.; Pale, P. Asymmetric synthesis of the cyclopentanones related to NCS and N1999A2 antitumor antibiotics. Tetrahedron Lett. 2003, 44, 3391-3395.
    • (2003) Tetrahedron Lett , vol.44 , pp. 3391-3395
    • Bertus, P.1    Zhang, J.H.2    Sir, G.3    Weibel, J.M.4    Pale, P.5
  • 13
    • 0001163468 scopus 로고
    • Calicheamicins: Discovery, structure, chemistry, and interaction with DNA
    • Lee, M.D.; Ellestad, G.A.; Borders, D.B. Calicheamicins: discovery, structure, chemistry, and interaction with DNA. Acc. Chem. Res. 1991, 24, 235-243.
    • (1991) Acc. Chem. Res , vol.24 , pp. 235-243
    • Lee, M.D.1    Ellestad, G.A.2    Borders, D.B.3
  • 14
    • 0039272886 scopus 로고    scopus 로고
    • Synthesis of the namenamicin A-C disaccharide: Towards the total synthesis of namenamicin
    • Weinstein, D.S.; Nicolaou, K.C. Synthesis of the namenamicin A-C disaccharide: towards the total synthesis of namenamicin. J. Chem. Soc., Perkin Trans. 1 1999, 545-547.
    • (1999) J. Chem. Soc., Perkin Trans , vol.1 , pp. 545-547
    • Weinstein, D.S.1    Nicolaou, K.C.2
  • 15
    • 0037467004 scopus 로고    scopus 로고
    • Shishijimicins A-C, novel enediyne antitumor antibiotics from the Ascidian Didemnum proliferum
    • Oku, N.; Matsunaga, S.; Fusetani, N. Shishijimicins A-C, novel enediyne antitumor antibiotics from the Ascidian Didemnum proliferum. J. Am. Chem. Soc. 2003, 125, 2044-2045.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 2044-2045
    • Oku, N.1    Matsunaga, S.2    Fusetani, N.3
  • 16
    • 0034090491 scopus 로고    scopus 로고
    • The synthesis of a sulfone containing analogue of the esperamicin-A(1) aglycone: A hetero Diels-Alder approach
    • Prabhakaran, J.; Lhermitte, H.; Das, J.; Sasi-Kumar, T.K.; Grierson, D.S. The synthesis of a sulfone containing analogue of the esperamicin-A(1) aglycone: A hetero Diels-Alder approach. Synlett 2000, 658-662.
    • (2000) Synlett , pp. 658-662
    • Prabhakaran, J.1    Lhermitte, H.2    Das, J.3    Sasi-Kumar, T.K.4    Grierson, D.S.5
  • 18
    • 0030848359 scopus 로고    scopus 로고
    • A convergent synthetic route to (+)-dynemicin A and analogs of wide structural variability
    • Myers, A.G.; Tom, N.J.; Fraley, M.E.; Cohen, S.B.; Madar, D.J. A convergent synthetic route to (+)-dynemicin A and analogs of wide structural variability. J. Am. Chem. Soc. 1997, 119, 6072-6094.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 6072-6094
    • Myers, A.G.1    Tom, N.J.2    Fraley, M.E.3    Cohen, S.B.4    Madar, D.J.5
  • 21
    • 0029886833 scopus 로고    scopus 로고
    • Oxygen dependence of the cytotoxicity of the enediyne anti-tumour antibiotic esperamicin A(1)
    • Batchelder, R.M.; Wilson, W.R.; Hay, M.P.; Denny, W.A. Oxygen dependence of the cytotoxicity of the enediyne anti-tumour antibiotic esperamicin A(1). Br. J. Cancer 1996, 74, S52-S56.
    • (1996) Br. J. Cancer , vol.74 , pp. S52-S56
    • Batchelder, R.M.1    Wilson, W.R.2    Hay, M.P.3    Denny, W.A.4
  • 23
    • 0034617818 scopus 로고    scopus 로고
    • Synthetic studies on calicheamicin g1 - synthesis of (-)-calicheamicinone and models representing the four sugars and the aromatic system
    • Clive, D.L.J.; Tao, Y.; Bo, Y.X.; Hu, Y.Z.; Selvakumar, N.; Sun, S.Y.; Daigneault, W.S.; Wu, Y.J. Synthetic studies on calicheamicin g1 - synthesis of (-)-calicheamicinone and models representing the four sugars and the aromatic system. Chem. Commun. 2000, 1341-1350.
    • (2000) Chem. Commun , pp. 1341-1350
    • Clive, D.L.J.1    Tao, Y.2    Bo, Y.X.3    Hu, Y.Z.4    Selvakumar, N.5    Sun, S.Y.6    Daigneault, W.S.7    Wu, Y.J.8
  • 24
    • 0032522273 scopus 로고    scopus 로고
    • Synthesis of the enediyne aglycon (+/-)-calicheamicinone
    • Churcher, I.; Hallet, D.; Magnus, P. Synthesis of the enediyne aglycon (+/-)-calicheamicinone. J. Am. Chem. Soc. 1998, 120, 3518-3519.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 3518-3519
    • Churcher, I.1    Hallet, D.2    Magnus, P.3
  • 25
    • 0034000656 scopus 로고    scopus 로고
    • The gene calC encodes for a non-heme iron metalloprotein responsible for calicheamicin self-resistance in Micromonospora
    • Whitwam, R.E.; Ahlert, J.; Holman, T.R.; Ruppen, M.; Thorson, J.S. The gene calC encodes for a non-heme iron metalloprotein responsible for calicheamicin self-resistance in Micromonospora. J. Am. Chem. Soc. 2000, 122, 1556-1557.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 1556-1557
    • Whitwam, R.E.1    Ahlert, J.2    Holman, T.R.3    Ruppen, M.4    Thorson, J.S.5
  • 29
    • 33845557570 scopus 로고
    • Evidence for the reactive spin state of 1,4-dehydrobenzenes
    • Lockhart, T.P.; Bergman, R.G. Evidence for the reactive spin state of 1,4-dehydrobenzenes. J. Am. Chem. Soc. 1981, 103, 4091-1096.
    • (1981) J. Am. Chem. Soc , vol.103 , pp. 4091-1096
    • Lockhart, T.P.1    Bergman, R.G.2
  • 30
    • 0037040670 scopus 로고    scopus 로고
    • Aromaticity of the Bergman, Myers-Saito, Schmittel, and directly related cyclizations of enediynes
    • Stahl, F.; Moran, D.; Schleyer, P.V.; Prall, M.; Schreiner, P.R. Aromaticity of the Bergman, Myers-Saito, Schmittel, and directly related cyclizations of enediynes. J. Org. Chem. 2002, 67, 1453-1461.
    • (2002) J. Org. Chem , vol.67 , pp. 1453-1461
    • Stahl, F.1    Moran, D.2    Schleyer, P.V.3    Prall, M.4    Schreiner, P.R.5
  • 32
    • 0026662154 scopus 로고
    • Design, synthesis, and study of simple monocyclic conjugated enediynes. The 10-membered ring enediyne moiety of the enediyne anticancer antibiotics
    • Nicolaou, K.C.; Zuccarello, G.; Riemer, C.; Estevez, V.A.; Dai, W.-M. Design, synthesis, and study of simple monocyclic conjugated enediynes. The 10-membered ring enediyne moiety of the enediyne anticancer antibiotics. J. Am. Chem. Soc. 1992, 114, 7360-7371.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 7360-7371
    • Nicolaou, K.C.1    Zuccarello, G.2    Riemer, C.3    Estevez, V.A.4    Dai, W.-M.5
  • 34
    • 85049949910 scopus 로고
    • Design of enediyne prodrugs
    • Maier, M.E. Design of enediyne prodrugs. Synlett 1995, 13-26.
    • (1995) Synlett , pp. 13-26
    • Maier, M.E.1
  • 35
    • 0000114294 scopus 로고
    • Monocyclic enediyne collapse to 1,4-diyl biradicals - a pathway under strain control
    • Snyder, J.P. Monocyclic enediyne collapse to 1,4-diyl biradicals - a pathway under strain control. J. Am. Chem. Soc. 1990, 112, 5367-5369.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 5367-5369
    • Snyder, J.P.1
  • 36
    • 2342481809 scopus 로고    scopus 로고
    • Lessons learned from marketed and investigational prodrugs
    • Ettmayer, P.; Amidon, G.L.; Clement, B.; Testa, B. Lessons learned from marketed and investigational prodrugs. J. Med. Chem. 2004, 47, 2393-2404.
    • (2004) J. Med. Chem , vol.47 , pp. 2393-2404
    • Ettmayer, P.1    Amidon, G.L.2    Clement, B.3    Testa, B.4
  • 37
    • 0036186160 scopus 로고    scopus 로고
    • A novel approach towards studying non-genotoxic enediynes as potential anticancer therapeutics
    • Hakimelahi, G.H.; Gassanov, G.S.; Hsu, M.-H.; Hwua, J.R.; Hakimelahi, S. A novel approach towards studying non-genotoxic enediynes as potential anticancer therapeutics. Bioorg. Med. Chem. 2002, 10, 1321-1328.
    • (2002) Bioorg. Med. Chem , vol.10 , pp. 1321-1328
    • Hakimelahi, G.H.1    Gassanov, G.S.2    Hsu, M.-H.3    Hwua, J.R.4    Hakimelahi, S.5
  • 38
    • 0034940771 scopus 로고    scopus 로고
    • A series of enediynes as novel inhibitors of topoisomerase I
    • Lin, C.F.; Hsieh, P.C.; Lu, W.D.; Chiu, H.F.; Wu, M.J. A series of enediynes as novel inhibitors of topoisomerase I. Bioorg. Med. Chem. 2001, 9, 1707-1711
    • (2001) Bioorg. Med. Chem , vol.9 , pp. 1707-1711
    • Lin, C.F.1    Hsieh, P.C.2    Lu, W.D.3    Chiu, H.F.4    Wu, M.J.5
  • 40
    • 0037170801 scopus 로고    scopus 로고
    • Benzene fused mono-cyclic enediynyl amides: Synthesis, reactivity and DNA-cleavage activity in comparison to the corresponding sulfonamides
    • Basak, A.; Mandal, S.; Kumar Das, A.; Bertolasi, V. Benzene fused mono-cyclic enediynyl amides: synthesis, reactivity and DNA-cleavage activity in comparison to the corresponding sulfonamides. Bioorg. Med. Chem. Lett. 2002, 12, 873-877.
    • (2002) Bioorg. Med. Chem. Lett , vol.12 , pp. 873-877
    • Basak, A.1    Mandal, S.2    Kumar Das, A.3    Bertolasi, V.4
  • 41
    • 0000428583 scopus 로고
    • Molecular design and chemical synthesis of potent enediynes. 1. Dynemicin model systems equipped with N-tethered triggering devices
    • Nicolaou, K.C.; Maligres, P.; Suzuki, T.; Wendeborn, S.V.; Dai, W.M.; Chadha, R.K. Molecular design and chemical synthesis of potent enediynes. 1. Dynemicin model systems equipped with N-tethered triggering devices. J. Am. Chem. Soc. 1992, 114, 8890-8907.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 8890-8907
    • Nicolaou, K.C.1    Maligres, P.2    Suzuki, T.3    Wendeborn, S.V.4    Dai, W.M.5    Chadha, R.K.6
  • 42
    • 0030586209 scopus 로고    scopus 로고
    • Efficient synthesis of a carbocyclic core moiety with the stereochemistry of the C-1027 chromophore
    • Sato, I.; Akahori, Y.; Iida, K.; Hirama, M. Efficient synthesis of a carbocyclic core moiety with the stereochemistry of the C-1027 chromophore. Tetrahedron Lett. 1996, 37, 5135-5138.
    • (1996) Tetrahedron Lett , vol.37 , pp. 5135-5138
    • Sato, I.1    Akahori, Y.2    Iida, K.3    Hirama, M.4
  • 43
    • 84989539773 scopus 로고
    • One-pot synthesis of haloacetylenes from trimethylsilyacetylenes
    • Nishikawa, T.; Shibuya, S.; Hosokawa, S.; Isobe, M. One-pot synthesis of haloacetylenes from trimethylsilyacetylenes. Synlett 1994, 485-1-86.
    • (1994) Synlett , pp. 485-486
    • Nishikawa, T.1    Shibuya, S.2    Hosokawa, S.3    Isobe, M.4
  • 44
    • 0027520529 scopus 로고
    • A photochemically triggered DNA-cleaving agent - synthesis, mechanistic and DNA cleavage studies on a new analog of the antitumor antibiotic dynemicin
    • Wender, P.A.; Zercher, C.K.; Beckham, S.; Haubold, E.M. A photochemically triggered DNA-cleaving agent - synthesis, mechanistic and DNA cleavage studies on a new analog of the antitumor antibiotic dynemicin. J. Org. Chem. 1993, 58, 5867-5869.
    • (1993) J. Org. Chem , vol.58 , pp. 5867-5869
    • Wender, P.A.1    Zercher, C.K.2    Beckham, S.3    Haubold, E.M.4
  • 45
    • 85064672431 scopus 로고
    • Cesium fluoride promoted cyclization in the synthesis of enediyne antibiotics
    • Nishikawa, T.; Shibuya, S.; Isobe, M. Cesium fluoride promoted cyclization in the synthesis of enediyne antibiotics. Synlett 1994, 482-484.
    • (1994) Synlett , pp. 482-484
    • Nishikawa, T.1    Shibuya, S.2    Isobe, M.3
  • 46
    • 0026763185 scopus 로고
    • 1- synthesis of 2-ketobicyclo[7.3.1] enediyne and 13-ketocyclo[7.3.1] enediyne cores mediated by η-2 dicobalt hexacarbonyl alkyne complexes - cycloaromatization rate studies
    • 1- synthesis of 2-ketobicyclo[7.3.1] enediyne and 13-ketocyclo[7.3.1] enediyne cores mediated by η-2 dicobalt hexacarbonyl alkyne complexes - cycloaromatization rate studies. J. Am. Chem. Soc. 1992, 114, 2544-2559.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 2544-2559
    • Magnus, P.1    Carter, P.2    Elliott, J.3    Lewis, R.4    Harling, J.5    Pitterna, T.6    Bauta, W.E.7    Fortt, S.8
  • 47
    • 0029929386 scopus 로고    scopus 로고
    • Studies on the synthesis of the core structures of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin
    • Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. Studies on the synthesis of the core structures of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin. Tetrahedron 1996, 52, 6283-6306.
    • (1996) Tetrahedron , vol.52 , pp. 6283-6306
    • Magnus, P.1    Carter, R.2    Davies, M.3    Elliott, J.4    Pitterna, T.5
  • 48
    • 0028337110 scopus 로고
    • Palladium-catalyzed reaction of (E) and (Z)-dichloroethenes with 1-alkynes. An efficient stereospecific synthesis of (e) and (Z)-enediynes
    • Chemin, D.; Linstrumelle, G. Palladium-catalyzed reaction of (E) and (Z)-dichloroethenes with 1-alkynes. An efficient stereospecific synthesis of (e) and (Z)-enediynes. Tetrahedron 1994, 50, 5335-5344.
    • (1994) Tetrahedron , vol.50 , pp. 5335-5344
    • Chemin, D.1    Linstrumelle, G.2
  • 49
    • 0031550881 scopus 로고    scopus 로고
    • Rational design, synthesis, and reactivity of lactendiynes, a new class of cyclic enediynes ortho-fused with the β-lactam ring
    • Banfi, L.; Basso, A.; Guanti, G. Rational design, synthesis, and reactivity of lactendiynes, a new class of cyclic enediynes ortho-fused with the β-lactam ring. Tetrahedron 1997, 53, 3249-3268.
    • (1997) Tetrahedron , vol.53 , pp. 3249-3268
    • Banfi, L.1    Basso, A.2    Guanti, G.3
  • 50
    • 0035178735 scopus 로고    scopus 로고
    • First synthesis of a highly strained cyclodeca-1,5-diyne skeleton via intramolecular Sonogashira cross-coupling
    • Dai, W.M.; Wu, A. First synthesis of a highly strained cyclodeca-1,5-diyne skeleton via intramolecular Sonogashira cross-coupling. Tetrahedron Lett. 2001, 42, 81-83.
    • (2001) Tetrahedron Lett , vol.42 , pp. 81-83
    • Dai, W.M.1    Wu, A.2
  • 52
    • 0344084140 scopus 로고    scopus 로고
    • Simplified dynemicin analogues: Diastereoselective synthesis and evaluation of their activity against plasmid DNA
    • Guanti, G.; Riva, R. Simplified dynemicin analogues: diastereoselective synthesis and evaluation of their activity against plasmid DNA. Org. Biomol. Chem. 2003, 1, 3967-3976.
    • (2003) Org. Biomol. Chem , vol.1 , pp. 3967-3976
    • Guanti, G.1    Riva, R.2
  • 53
    • 2342612071 scopus 로고    scopus 로고
    • Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle
    • Banfi, L.; Basso, A.; Gandolfo, V.; Guanti, G.; Riva, R. Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle. Tetrahedron Lett. 2004, 45, 4221-4223.
    • (2004) Tetrahedron Lett , vol.45 , pp. 4221-4223
    • Banfi, L.1    Basso, A.2    Gandolfo, V.3    Guanti, G.4    Riva, R.5
  • 54
    • 0033546365 scopus 로고    scopus 로고
    • Effects of propargylic substitution and annelation on the cycloaromatization of a bicyclo[7.3.1]enediyne
    • Moss, D.K.; Spence, J.D.; Nantz, M.H. Effects of propargylic substitution and annelation on the cycloaromatization of a bicyclo[7.3.1]enediyne. J. Org. Chem. 1999, 64, 4339-4343.
    • (1999) J. Org. Chem , vol.64 , pp. 4339-4343
    • Moss, D.K.1    Spence, J.D.2    Nantz, M.H.3
  • 55
    • 0001451692 scopus 로고
    • Design and synthesis of a system for enediyne formation by anthraquinone reductive activation
    • Myers, A.G.; Dragovich, P.S. Design and synthesis of a system for enediyne formation by anthraquinone reductive activation. J. Am. Chem. Soc. 1992, 114, 5859-5860.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 5859-5860
    • Myers, A.G.1    Dragovich, P.S.2
  • 56
    • 0034016206 scopus 로고    scopus 로고
    • New approach to β-lactam-fused enediynes ("lactenediynes") by stereoselective pinacol coupling
    • Banfi, L.; Basso, A.; Guanti, G. New approach to β-lactam-fused enediynes ("lactenediynes") by stereoselective pinacol coupling. Eur. J. Org. Chem. 2000, 939-946.
    • (2000) Eur. J. Org. Chem , pp. 939-946
    • Banfi, L.1    Basso, A.2    Guanti, G.3
  • 57
    • 0037144709 scopus 로고    scopus 로고
    • Synthesis and structure of a stabilized 10-membered cyclic enediyne
    • Pitsch, W.; Klein, M.; Zabel, M.; König, B. Synthesis and structure of a stabilized 10-membered cyclic enediyne. J. Org. Chem. 2002, 67, 6805-6807.
    • (2002) J. Org. Chem , vol.67 , pp. 6805-6807
    • Pitsch, W.1    Klein, M.2    Zabel, M.3    König, B.4
  • 58
    • 0027300097 scopus 로고
    • Cyclic conjugated enediynes via elimination of a thionocarbonate in a latent Z-hex-3-ene-1,5-diyne unit
    • Semmelhack, M.F.; Gallagher, J. Cyclic conjugated enediynes via elimination of a thionocarbonate in a latent Z-hex-3-ene-1,5-diyne unit. Tetrahedron Lett. 1993, 34, 4121-4124.
    • (1993) Tetrahedron Lett , vol.34 , pp. 4121-4124
    • Semmelhack, M.F.1    Gallagher, J.2
  • 59
    • 0032985327 scopus 로고    scopus 로고
    • Synthesis of fully-substituted enediynes by the Corey-Winter reaction
    • Crich, D.; Pavlovich, A.B.; Wink, D.J. Synthesis of fully-substituted enediynes by the Corey-Winter reaction. Synth. Commun. 1999, 29, 359-377.
    • (1999) Synth. Commun , vol.29 , pp. 359-377
    • Crich, D.1    Pavlovich, A.B.2    Wink, D.J.3
  • 60
    • 37049086512 scopus 로고
    • Towards enediyne libraries: Cyclic enediynes via an intramolecular carbenoid coupling protocol
    • Jones, G.B.; Huber, R.S.; Mathews, J.E. Towards enediyne libraries: cyclic enediynes via an intramolecular carbenoid coupling protocol. J. Chem. Soc., Chem. Commun. 1995, 1791-1792.
    • (1995) J. Chem. Soc., Chem. Commun , pp. 1791-1792
    • Jones, G.B.1    Huber, R.S.2    Mathews, J.E.3
  • 61
    • 0004512579 scopus 로고    scopus 로고
    • Synthesis and metal ion binding studies of enediyne-containing crown ethers
    • McPhee, M.M.; Kerwin, S.M. Synthesis and metal ion binding studies of enediyne-containing crown ethers. J. Org. Chem. 1996, 61, 9385-9393.
    • (1996) J. Org. Chem , vol.61 , pp. 9385-9393
    • McPhee, M.M.1    Kerwin, S.M.2
  • 62
    • 0029113989 scopus 로고
    • Synthesis and characterization of nine-membered cyclic enediynes, models of the C-1027 and kedarcidin chromophores: Equilibration with a p-benzyne biradical and kinetic stabilization
    • Iida, K.; Hirama, M. Synthesis and characterization of nine-membered cyclic enediynes, models of the C-1027 and kedarcidin chromophores: equilibration with a p-benzyne biradical and kinetic stabilization. J. Am. Chem. Soc. 1995, 117, 8875-8876.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 8875-8876
    • Iida, K.1    Hirama, M.2
  • 63
    • 0042355731 scopus 로고    scopus 로고
    • Conformational control in activation of an enediyne
    • Semmelhack, M.F.; Wu, L.; Pascal, R.A.J.; Ho, D.M. Conformational control in activation of an enediyne. J. Am. Chem. Soc. 2003, 125, 10496-10497.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 10496-10497
    • Semmelhack, M.F.1    Wu, L.2    Pascal, R.A.J.3    Ho, D.M.4
  • 64
    • 0030498845 scopus 로고    scopus 로고
    • DNA cleavage by a nine-membered masked enediyne, an analogue of the kedarcidin and C-1027 chromophores
    • Takahashi, T.; Tanaka, H.; Yamada, H.; Matsumoto, T.; Sugiura, Y. DNA cleavage by a nine-membered masked enediyne, an analogue of the kedarcidin and C-1027 chromophores. Angew. Chem., Int. Ed. Engl. 1996, 35, 1835-1836.
    • (1996) Angew. Chem., Int. Ed. Engl , vol.35 , pp. 1835-1836
    • Takahashi, T.1    Tanaka, H.2    Yamada, H.3    Matsumoto, T.4    Sugiura, Y.5
  • 65
    • 0025759913 scopus 로고
    • The esperamicin-calicheamicin aglycones: Ring closure of a simple strained system mediated by chromium(II)-nickel(II) salts
    • Crevisy, C.; Beau, J.-M. The esperamicin-calicheamicin aglycones: ring closure of a simple strained system mediated by chromium(II)-nickel(II) salts. Tetrahedron Lett. 1991, 32, 3171-3174.
    • (1991) Tetrahedron Lett , vol.32 , pp. 3171-3174
    • Crevisy, C.1    Beau, J.-M.2
  • 66
    • 0345254949 scopus 로고    scopus 로고
    • Tetrahydroxy 10-membered cyclic enediynes
    • Klein, M.; Zabel, M.; Bernhardt, G.; Konig, B. Tetrahydroxy 10-membered cyclic enediynes. J. Org. Chem. 2003, 68, 9379-9383
    • (2003) J. Org. Chem , vol.68 , pp. 9379-9383
    • Klein, M.1    Zabel, M.2    Bernhardt, G.3    Konig, B.4
  • 67
    • 0034564008 scopus 로고    scopus 로고
    • A mild route to a-alkoxyacetylenes mediated by Lewis acids and synthetic routes to 10-,11- and 12-membered ring enediyne carbocycles
    • Comanita, B.M.; Heuft, M.A.; Rietveld, T.; Fallis, A.G. A mild route to a-alkoxyacetylenes mediated by Lewis acids and synthetic routes to 10-,11- and 12-membered ring enediyne carbocycles. Israel J. Chem. 2000, 40, 241-253.
    • (2000) Israel J. Chem , vol.40 , pp. 241-253
    • Comanita, B.M.1    Heuft, M.A.2    Rietveld, T.3    Fallis, A.G.4
  • 69
    • 0037178348 scopus 로고    scopus 로고
    • Halo-enediynes: Probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization
    • Plourde, G.W.I.; Warner, P.M.; Parrish, D.A.; Jones, G.B. Halo-enediynes: Probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization. J. Org. Chem. 2002, 67, 5369-5374.
    • (2002) J. Org. Chem , vol.67 , pp. 5369-5374
    • Plourde, G.W.I.1    Warner, P.M.2    Parrish, D.A.3    Jones, G.B.4
  • 71
    • 0031576892 scopus 로고    scopus 로고
    • Bifunctional antitumor agents: A DNA interactive enediyne from the pyrrolo[9,10-b]phenanthrene template
    • Jones, G.B.; Mathews, G.E. Bifunctional antitumor agents: a DNA interactive enediyne from the pyrrolo[9,10-b]phenanthrene template. Bioorg. Med. Chem. Lett. 1997, 7, 745-748
    • (1997) Bioorg. Med. Chem. Lett , vol.7 , pp. 745-748
    • Jones, G.B.1    Mathews, G.E.2
  • 72
    • 0030765221 scopus 로고    scopus 로고
    • Bifunctional antitumor agents. Derivatives of pyrrolo[9,10-b]phenanthrene - A DNA intercalative delivery template
    • Jones, G.B.; Mathews, J.E. Bifunctional antitumor agents. Derivatives of pyrrolo[9,10-b]phenanthrene - A DNA intercalative delivery template. Tetrahedron 1997, 53, 14599-14614.
    • (1997) Tetrahedron , vol.53 , pp. 14599-14614
    • Jones, G.B.1    Mathews, J.E.2
  • 73
    • 0030889815 scopus 로고    scopus 로고
    • The oxide anion accelerated retro-Diels-Alder reaction
    • Bunnage, M.E.; Nicolaou, K.C. The oxide anion accelerated retro-Diels-Alder reaction. Chem. Eur. J. 1997, 3, 187-192.
    • (1997) Chem. Eur. J , vol.3 , pp. 187-192
    • Bunnage, M.E.1    Nicolaou, K.C.2
  • 74
    • 0037075145 scopus 로고    scopus 로고
    • DNA cleavage potency, cytotoxicity, and mechanism of action of a novel class of enediyne prodrugs
    • Dai, W.M.; Lai, K.W.; Wu, A. X.; Hamaguchi, W.; Lee, M.Y. H.; Zhou, L.; Ishii, A.; Nishimoto, S. DNA cleavage potency, cytotoxicity, and mechanism of action of a novel class of enediyne prodrugs. J. Med. Chem. 2002, 45, 758-761.
    • (2002) J. Med. Chem , vol.45 , pp. 758-761
    • Dai, W.M.1    Lai, K.W.2    Wu, A.X.3    Hamaguchi, W.4    Lee, M.Y.H.5    Zhou, L.6    Ishii, A.7    Nishimoto, S.8
  • 75
    • 0026710825 scopus 로고
    • Arene 1,4-Diradical formation from o-dialkynylarenes
    • Semmelhack, M.F.; Neu, T.; Foubelo, F. Arene 1,4-Diradical formation from o-dialkynylarenes. Tetrahedron Lett. 1992, 33, 3277-3280.
    • (1992) Tetrahedron Lett , vol.33 , pp. 3277-3280
    • Semmelhack, M.F.1    Neu, T.2    Foubelo, F.3
  • 76
    • 0033525469 scopus 로고    scopus 로고
    • Benzannelation alters the rate limiting step in enediyne cycloaromatization
    • Taneko, T.; Takahashi, M.; Hirama, M. Benzannelation alters the rate limiting step in enediyne cycloaromatization. Tetrahedron Lett. 1999, 40, 2015-2018.
    • (1999) Tetrahedron Lett , vol.40 , pp. 2015-2018
    • Taneko, T.1    Takahashi, M.2    Hirama, M.3
  • 77
    • 0027199861 scopus 로고
    • CDPI3-enediyne and CDPI3-EDTA conjugates: A new class of DNA cleaving agents
    • Boger, D.L.; Zhou, J. CDPI3-enediyne and CDPI3-EDTA conjugates: a new class of DNA cleaving agents. J. Org. Chem. 1993, 58, 3018-3024.
    • (1993) J. Org. Chem , vol.58 , pp. 3018-3024
    • Boger, D.L.1    Zhou, J.2
  • 78
    • 0027050497 scopus 로고
    • Redox-controlled Bergman cycloaromatizations. Designed enediynes with DNA-cleaving properties and antitumor activity
    • Nicolaou, K.C.; Liu, A.; Zeng, Z.; McComb, S. Redox-controlled Bergman cycloaromatizations. Designed enediynes with DNA-cleaving properties and antitumor activity. J. Am. Chem. Soc. 1992, 114, 9279-9282.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 9279-9282
    • Nicolaou, K.C.1    Liu, A.2    Zeng, Z.3    McComb, S.4
  • 79
    • 0034736380 scopus 로고    scopus 로고
    • Photochemical and thermal Bergman cyclization of a pyrimidine enediynol and enediynone
    • Choy, N.; Blanco, B.; Wen, J.; Krishnan, A.; Russell, K.C. Photochemical and thermal Bergman cyclization of a pyrimidine enediynol and enediynone. Organic Lett. 2000, 2, 3761-3764.
    • (2000) Organic Lett , vol.2 , pp. 3761-3764
    • Choy, N.1    Blanco, B.2    Wen, J.3    Krishnan, A.4    Russell, K.C.5
  • 80
    • 0025098766 scopus 로고
    • The synthesis of a 10-membered benzo-oxadiyne ring
    • Singh, R.; Just, G. The synthesis of a 10-membered benzo-oxadiyne ring. Tetrahedron Lett. 1990, 31, 185-188.
    • (1990) Tetrahedron Lett , vol.31 , pp. 185-188
    • Singh, R.1    Just, G.2
  • 81
    • 0034686527 scopus 로고    scopus 로고
    • DNA-cleavage studies on N-substituted monocyclic enediynes: Enhancement of potency by incorporation of intercalating or electron poor aromatic ring and subsequent design of a novel phototriggerable acyclic enediyne
    • Basak, A.; Bdour, H.M.; Shain, J.C.; Mandal, S.; Rudra, K.R.; Nag, S. DNA-cleavage studies on N-substituted monocyclic enediynes: Enhancement of potency by incorporation of intercalating or electron poor aromatic ring and subsequent design of a novel phototriggerable acyclic enediyne. Bioorg. Med. Chem. Lett. 2000, 10, 1321-1325.
    • (2000) Bioorg. Med. Chem. Lett , vol.10 , pp. 1321-1325
    • Basak, A.1    Bdour, H.M.2    Shain, J.C.3    Mandal, S.4    Rudra, K.R.5    Nag, S.6
  • 82
    • 0038306205 scopus 로고    scopus 로고
    • Synthesis, reactions and DNA damaging abilities of 10-membered enediyne-sulfone and related compounds
    • Suzuki, I.; Shigenaga, A.; Manabe, A.; Nemoto, H.; Shibuya, M. Synthesis, reactions and DNA damaging abilities of 10-membered enediyne-sulfone and related compounds. Tetrahedron 2003, 59, 5691-5704.
    • (2003) Tetrahedron , vol.59 , pp. 5691-5704
    • Suzuki, I.1    Shigenaga, A.2    Manabe, A.3    Nemoto, H.4    Shibuya, M.5
  • 83
    • 0037391634 scopus 로고    scopus 로고
    • Intramolecular opening of β-lactams with amines as a strategy toward enzymatically or photochemically triggered activation of lactenediyne prodrugs
    • Banfi, L.; Guanti, G.; Rasparini, M. Intramolecular opening of β-lactams with amines as a strategy toward enzymatically or photochemically triggered activation of lactenediyne prodrugs. Eur. J. Org. Chem. 2003, 1319-1336.
    • (2003) Eur. J. Org. Chem , pp. 1319-1336
    • Banfi, L.1    Guanti, G.2    Rasparini, M.3
  • 84
    • 0030761988 scopus 로고    scopus 로고
    • A new framework for the cycloaromatization of enediynes under mild conditions
    • Semmelhack, M.F.; Gu, Y.; Ho, D.M. A new framework for the cycloaromatization of enediynes under mild conditions. Tetrahedron Lett. 1997, 38, 5583-5586.
    • (1997) Tetrahedron Lett , vol.38 , pp. 5583-5586
    • Semmelhack, M.F.1    Gu, Y.2    Ho, D.M.3
  • 85
    • 0037043056 scopus 로고    scopus 로고
    • A simple synthesis and evaluation of the bicyclo[8.3.0]enediyne framework
    • Semmelhack, M.F.; Jaskowski, M.; Sarpong, R.; Ho, D.M. A simple synthesis and evaluation of the bicyclo[8.3.0]enediyne framework. Tetrahedron Lett. 2002, 43, 4947-4950.
    • (2002) Tetrahedron Lett , vol.43 , pp. 4947-4950
    • Semmelhack, M.F.1    Jaskowski, M.2    Sarpong, R.3    Ho, D.M.4
  • 86
    • 33748246916 scopus 로고
    • Estramycins: A new diyl precursor family derived from estradiol
    • Wang, J.; De Clercq, P.J. Estramycins: a new diyl precursor family derived from estradiol. Angew. Chem., Int. Ed. Engl. 1995, 34, 1749-1752.
    • (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 1749-1752
    • Wang, J.1    de Clercq, P.J.2
  • 87
    • 0037037840 scopus 로고    scopus 로고
    • Synthesis of a new lactenediyne scaffold equipped with three handles
    • Banfi, L.; Guanti, G. Synthesis of a new lactenediyne scaffold equipped with three handles. Tetrahedron Lett. 2002, 43, 7427-7429.
    • (2002) Tetrahedron Lett , vol.43 , pp. 7427-7429
    • Banfi, L.1    Guanti, G.2
  • 88
    • 0036859322 scopus 로고    scopus 로고
    • Synthesis of intramolecularly activated lactenediynes and evaluation of their activity against plasmid DNA
    • Banfi, L.; Guanti, G. Synthesis of intramolecularly activated lactenediynes and evaluation of their activity against plasmid DNA. Eur. J. Org. Chem. 2002, 3745-3755.
    • (2002) Eur. J. Org. Chem , pp. 3745-3755
    • Banfi, L.1    Guanti, G.2
  • 90
    • 0029839133 scopus 로고    scopus 로고
    • An approach towards more selective anticancer agents
    • Eisenbrand, G.; Lauck-Birkel, S.; Tang, W.C. An approach towards more selective anticancer agents. Synthesis 1996, 1246-1258
    • (1996) Synthesis , pp. 1246-1258
    • Eisenbrand, G.1    Lauck-Birkel, S.2    Tang, W.C.3
  • 91
    • 0031558240 scopus 로고    scopus 로고
    • Antibody-directed enzyme prodrug therapy (ADEPT): A review
    • Niculescu-Duvaz, I.; Springer, C.J. Antibody-directed enzyme prodrug therapy (ADEPT): a review. Adv. Drug Delivery Rev. 1997, 26, 151-172.
    • (1997) Adv. Drug Delivery Rev , vol.26 , pp. 151-172
    • Niculescu-Duvaz, I.1    Springer, C.J.2
  • 92
  • 93
    • 0037013837 scopus 로고    scopus 로고
    • A carbene insertion route to β-lactam fused cyclic enediynes
    • Basak, A.; Mandal, S. A carbene insertion route to β-lactam fused cyclic enediynes. Tetrahedron Lett. 2002, 43, 4241-4243
    • (2002) Tetrahedron Lett , vol.43 , pp. 4241-4243
    • Basak, A.1    Mandal, S.2
  • 94
    • 0001997760 scopus 로고    scopus 로고
    • Synthesis of N-fused "Lactendiynes"
    • Banfi, L.; Guanti, G. Synthesis of N-fused "Lactendiynes". Eur. J. Org. Chem. 1998, 1543-1548.
    • (1998) Eur. J. Org. Chem , pp. 1543-1548
    • Banfi, L.1    Guanti, G.2
  • 95
    • 0006582377 scopus 로고
    • A core system that simulates the cycloaro-matization and DNA cleavage properties of calicheamicin-esperamicin: A correlation experiment
    • Mantlo, N.B.; Danishefsky, S.J. A core system that simulates the cycloaro-matization and DNA cleavage properties of calicheamicin-esperamicin: a correlation experiment. J. Org. Chem. 1989, 54, 2781-2783.
    • (1989) J. Org. Chem , vol.54 , pp. 2781-2783
    • Mantlo, N.B.1    Danishefsky, S.J.2
  • 96
    • 0027772649 scopus 로고
    • The enol-keto trigger in initiating arene diradical formation in calicheamicin/esperamicin analogs
    • Semmelhack, M.F.; Gallagher, J.J.; Minami, T.; Date, T. The enol-keto trigger in initiating arene diradical formation in calicheamicin/esperamicin analogs. J. Am. Chem. Soc. 1993, 115, 11618-11619.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 11618-11619
    • Semmelhack, M.F.1    Gallagher, J.J.2    Minami, T.3    Date, T.4
  • 97
    • 0037148015 scopus 로고    scopus 로고
    • Evaluation ofalkene isomerization as a trigger for enediyne activation
    • Semmelhack, M.F.; Sarpong, R.; Bergman, J.; Ho, D.M. Evaluation ofalkene isomerization as a trigger for enediyne activation. Tetrahedron Lett. 2002, 43, 541-544.
    • (2002) Tetrahedron Lett , vol.43 , pp. 541-544
    • Semmelhack, M.F.1    Sarpong, R.2    Bergman, J.3    Ho, D.M.4
  • 100
    • 85047676352 scopus 로고    scopus 로고
    • 1998 Alfred Bader award lecture. Tangents and targets: The synthetic highway from natural products to medicine
    • Fallis, A.G. 1998 Alfred Bader award lecture. Tangents and targets: the synthetic highway from natural products to medicine. Can. J. Chem. 1999, 77, 159-177.
    • (1999) Can. J. Chem , vol.77 , pp. 159-177
    • Fallis, A.G.1
  • 102
    • 0025866083 scopus 로고
    • Enediyne compounds equipped with acid-, base, and photo-sensitive triggering devices. Chemical simulation of the dynemicin A reaction cascade
    • Nicolaou, K.C.; Dai, W.-M.; Wendeborn, S.V.; Smith, A.L.; Torisawa, Y.; Maligres, P.; Hwang, C.-K. Enediyne compounds equipped with acid-, base, and photo-sensitive triggering devices. Chemical simulation of the dynemicin A reaction cascade. Angew. Chem., Int. Ed. Engl. 1991, 30, 1032-1036.
    • (1991) Angew. Chem., Int. Ed. Engl , vol.30 , pp. 1032-1036
    • Nicolaou, K.C.1    Dai, W.-M.2    Wendeborn, S.V.3    Smith, A.L.4    Torisawa, Y.5    Maligres, P.6    Hwang, C.-K.7
  • 103
    • 0031030379 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel cyclic enediyne compounds related to dynemicin A as antitumor agents
    • Unno, R.; Michishita, H.; Inagaki, H.; Baba, Y.; Jomori, T.; Nishikawa, T.; Isobe, M. Synthesis and biological evaluation of novel cyclic enediyne compounds related to dynemicin A as antitumor agents. Chem. Pharm. Bull. 1997, 45, 125-133.
    • (1997) Chem. Pharm. Bull , vol.45 , pp. 125-133
    • Unno, R.1    Michishita, H.2    Inagaki, H.3    Baba, Y.4    Jomori, T.5    Nishikawa, T.6    Isobe, M.7
  • 104
    • 0028793511 scopus 로고
    • A novel endiyne prodrug for antibody-directed enzyme prodrug therapy (ADEPT) using E. coli B nitroreductase
    • Hay, M.P.; Wilson, W.R.; Denny, W.A. A novel endiyne prodrug for antibody-directed enzyme prodrug therapy (ADEPT) using E. coli B nitroreductase. Bioorg. Med. Chem. Lett. 1995, 5, 2829-2834.
    • (1995) Bioorg. Med. Chem. Lett , vol.5 , pp. 2829-2834
    • Hay, M.P.1    Wilson, W.R.2    Denny, W.A.3
  • 105
    • 1542267801 scopus 로고    scopus 로고
    • Prodrugs of dynemicin analogs for selective chemotherapy mediated by an aldolase catalytic Ab
    • Sinha, S.C.; Li, L.-S.; Miller, G.P.; Dutta, S.; Rader, C.; Lerner, R.A. Prodrugs of dynemicin analogs for selective chemotherapy mediated by an aldolase catalytic Ab. Proc. Natl. Acad. Sci. USA 2004, 101, 3095-3099.
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 3095-3099
    • Sinha, S.C.1    Li, L.-S.2    Miller, G.P.3    Dutta, S.4    Rader, C.5    Lerner, R.A.6
  • 106
    • 0026352504 scopus 로고
    • Novel enediynes equipped with triggering and detection devices. Isolation of cis-diol models of the dynemicin cascade
    • Nicolaou, K.C.; Hong, Y.-P.; Torisawa, Y.; Tsay, S.-C.; Dai, W.-M. Novel enediynes equipped with triggering and detection devices. Isolation of cis-diol models of the dynemicin cascade. J. Am. Chem. Soc. 1991, 113, 9878-9880.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 9878-9880
    • Nicolaou, K.C.1    Hong, Y.-P.2    Torisawa, Y.3    Tsay, S.-C.4    Dai, W.-M.5
  • 107
    • 33751144977 scopus 로고
    • Enediyne quinone imines: Truncated biologically active dynemicin congeners
    • Shair, M.D.; Yoon, T.; Chou, T.-C.; Danishefsky, S. J. Enediyne quinone imines: truncated biologically active dynemicin congeners. Angew. Chem., Int. Ed. Engl. 1994, 33, 2477-2479
    • (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 2477-2479
    • Shair, M.D.1    Yoon, T.2    Chou, T.-C.3    Danishefsky, S.J.4
  • 108
    • 0030001543 scopus 로고    scopus 로고
    • The total synthesis of dynemicin A leading to development of a fully contained bioreductively activated enediyne prodrug
    • Shair, M.D.; Yoon, T.Y.; Mosny, K.K.; Chou, T.C.; Danishefsky, S.J. The total synthesis of dynemicin A leading to development of a fully contained bioreductively activated enediyne prodrug. J. Am. Chem. Soc. 1996, 118, 9509-9525.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 9509-9525
    • Shair, M.D.1    Yoon, T.Y.2    Mosny, K.K.3    Chou, T.C.4    Danishefsky, S.J.5
  • 109
    • 16144364301 scopus 로고    scopus 로고
    • Synthesis of an esperamicin core analog with an epoxide trigger
    • Mastalerz, H.; Doyle, T.W.; Kadow, J.F.; Vyas, D.M. Synthesis of an esperamicin core analog with an epoxide trigger. Tetrahedron Lett. 1996, 37, 8683-8686.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8683-8686
    • Mastalerz, H.1    Doyle, T.W.2    Kadow, J.F.3    Vyas, D.M.4
  • 110
    • 0030602215 scopus 로고    scopus 로고
    • Synthesis of a hybrid analog of the esperamicin and dynemicin cores
    • Mastalerz, H.; Doyle, T.W.; Kadow, J.F.; Vyas, D.M. Synthesis of a hybrid analog of the esperamicin and dynemicin cores. Tetrahedron Lett. 1996, 37, 8687-8690.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8687-8690
    • Mastalerz, H.1    Doyle, T.W.2    Kadow, J.F.3    Vyas, D.M.4
  • 112
    • 0030842824 scopus 로고    scopus 로고
    • Synthetic and mechanistic studies on the azabicyclo[7.3.1]enediyne core and naphtho[2,3-h]quinoline portions ofdynemicin A
    • Magnus, P.; Eisenbeis, S.A.; Fairhurst, R.A.; Iliadis, T.; Magnus, N.A.; Parry, D. Synthetic and mechanistic studies on the azabicyclo[7.3.1]enediyne core and naphtho[2,3-h]quinoline portions ofdynemicin A. J. Am. Chem. Soc. 1997, 119, 5591-5605.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 5591-5605
    • Magnus, P.1    Eisenbeis, S.A.2    Fairhurst, R.A.3    Iliadis, T.4    Magnus, N.A.5    Parry, D.6
  • 113
    • 0027819038 scopus 로고
    • Studies on dynemicin. A nonradical cycloaromatization pathway for the azabicyclo [7.3.1]enediyne core structure initiated by thiolate addition
    • Magnus, P.; Eisenbeis, S.A.; Rose, W.C.; Zein, N.; Solomon, W. Studies on dynemicin. A nonradical cycloaromatization pathway for the azabicyclo [7.3.1]enediyne core structure initiated by thiolate addition. J. Am. Chem. Soc. 1993, 115, 12627-12628.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 12627-12628
    • Magnus, P.1    Eisenbeis, S.A.2    Rose, W.C.3    Zein, N.4    Solomon, W.5
  • 114
    • 0034130473 scopus 로고    scopus 로고
    • Straightforward access to [6]metacyclophene-based enynes by an inter-intramolecular tandem etherification through a one-pot double SNAr reaction
    • Suffert, J.; Raeppel, S.; Raeppel, F.; Didier, B. Straightforward access to [6]metacyclophene-based enynes by an inter-intramolecular tandem etherification through a one-pot double SNAr reaction. Synlett 2000, 874-876.
    • (2000) Synlett , pp. 874-876
    • Suffert, J.1    Raeppel, S.2    Raeppel, F.3    Didier, B.4
  • 115
    • 0041488338 scopus 로고    scopus 로고
    • Synthesis, structure and reactivity of enediyne macrocycles
    • Konig, B.; Pitsch, W.; Thondorf, I. Synthesis, structure and reactivity of enediyne macrocycles. J. Org. Chem. 1996, 61, 4258-4261.
    • (1996) J. Org. Chem , vol.61 , pp. 4258-4261
    • Konig, B.1    Pitsch, W.2    Thondorf, I.3
  • 116
    • 0042990949 scopus 로고    scopus 로고
    • Changing the reactivity of enediynes by metal-ion coordination
    • Konig, B. Changing the reactivity of enediynes by metal-ion coordination. Eur. J. Org. Chem. 2000, 381-385
    • (2000) Eur. J. Org. Chem , pp. 381-385
    • Konig, B.1
  • 117
    • 0142200418 scopus 로고    scopus 로고
    • Chelation control in Bergman cyclization. Synthesis and reactivity of enediynyl ligands
    • Basak, A.; Mandal, S.; Bag, S.S. Chelation control in Bergman cyclization. Synthesis and reactivity of enediynyl ligands. Chem. Rev. 2003, 103, 4077-4094.
    • (2003) Chem. Rev , vol.103 , pp. 4077-4094
    • Basak, A.1    Mandal, S.2    Bag, S.S.3
  • 118
    • 0001409177 scopus 로고
    • Electron acceptor substituents at terminal alkyne carbons
    • Koga, N.; Morokuma, K. Electron acceptor substituents at terminal alkyne carbons. J. Am. Chem. Soc. 1991, 113, 1907-1911.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 1907-1911
    • Koga, N.1    Morokuma, K.2
  • 119
    • 0035478821 scopus 로고    scopus 로고
    • Substituent effects on the Bergman cyclization of (Z)-1,5-hexadiyne-3-enes: A systematic computational study
    • Prall, M.; Wittkopp, A.; Fokin, A.A.; Schreiner, P.R. Substituent effects on the Bergman cyclization of (Z)-1,5-hexadiyne-3-enes: A systematic computational study. J. Comput. Chem. 2001, 22, 1605-1614.
    • (2001) J. Comput. Chem , vol.22 , pp. 1605-1614
    • Prall, M.1    Wittkopp, A.2    Fokin, A.A.3    Schreiner, P.R.4
  • 121
    • 0347600556 scopus 로고    scopus 로고
    • Synthesis and thermal cyclization of an enediyne-sulfonamide
    • Klein, M.; Konig, B. Synthesis and thermal cyclization of an enediyne-sulfonamide. Tetrahedron 2004, 60, 1087-1092.
    • (2004) Tetrahedron , vol.60 , pp. 1087-1092
    • Klein, M.1    Konig, B.2
  • 122
    • 0034700568 scopus 로고    scopus 로고
    • Syntheses and thermal reactivities of symmetrically and asymmetrically substituted acyclic enediynes: Steric control of Bergman cyclization temperatures
    • Rawat, D.S.; Zaleski, J.M. Syntheses and thermal reactivities of symmetrically and asymmetrically substituted acyclic enediynes: steric control of Bergman cyclization temperatures. Chem. Commun. 2000, 2493-2494.
    • (2000) Chem. Commun , pp. 2493-2494
    • Rawat, D.S.1    Zaleski, J.M.2
  • 123
    • 0028225955 scopus 로고
    • Synthesis and reactivity of the first bis(crown ether) enediyne
    • Konig, B.; Rutters, H. Synthesis and reactivity of the first bis(crown ether) enediyne. Tetrahedron Lett. 1994, 35, 3501-3504.
    • (1994) Tetrahedron Lett , vol.35 , pp. 3501-3504
    • Konig, B.1    Rutters, H.2
  • 124
    • 0029150062 scopus 로고
    • Controlled acceleration and inhibition of Bergman cyclization by metal chlorides
    • Warner, B.P.; Millar, S.P.; Broene, R.D.; Buchwald, S.L. Controlled acceleration and inhibition of Bergman cyclization by metal chlorides. Science 1995, 269, 814-816.
    • (1995) Science , vol.269 , pp. 814-816
    • Warner, B.P.1    Millar, S.P.2    Broene, R.D.3    Buchwald, S.L.4
  • 125
    • 0000005509 scopus 로고
    • An organometallic diradical cycloaromatization reaction
    • Wang, Y.; Finn, M.G. An organometallic diradical cycloaromatization reaction. J. Am. Chem. Soc. 1995, 117, 8045-8046.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 8045-8046
    • Wang, Y.1    Finn, M.G.2
  • 126
    • 0001380819 scopus 로고
    • Thermal generation of alpha,3-dehydrotoluene from (Z)-1,2,4-heptatrien-6-yne
    • Myers, A.G.; Kuo, E.Y.; Finney, N.S. Thermal generation of alpha,3-dehydrotoluene from (Z)-1,2,4-heptatrien-6-yne. J. Am. Chem. Soc. 1989, 111, 8057-8058
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 8057-8058
    • Myers, A.G.1    Kuo, E.Y.2    Finney, N.S.3
  • 127
    • 0024343657 scopus 로고
    • Biradical formation from acyclic conjugated eneyne-allene system related to neo-carzinostatin and esperamicin-calichemicin
    • Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Biradical formation from acyclic conjugated eneyne-allene system related to neo-carzinostatin and esperamicin-calichemicin. Tetrahedron Lett. 1989, 30, 4995-4998.
    • (1989) Tetrahedron Lett , vol.30 , pp. 4995-4998
    • Nagata, R.1    Yamanaka, H.2    Okazaki, E.3    Saito, I.4
  • 128
    • 0030066058 scopus 로고    scopus 로고
    • Cycloaromatization of enediyne model compounds via a reaction cascade triggered by hydrolysis of the a-alkynylmalonates
    • Shibuya, M.; Wakayama, M.; Naoe, Y.; Kawakami, T.; Ishigaki, K.; Nemoto, H.; Shimizu, H.; Nagao, Y. Cycloaromatization of enediyne model compounds via a reaction cascade triggered by hydrolysis of the a-alkynylmalonates. Tetrahedron Lett. 1996, 37, 865-868.
    • (1996) Tetrahedron Lett , vol.37 , pp. 865-868
    • Shibuya, M.1    Wakayama, M.2    Naoe, Y.3    Kawakami, T.4    Ishigaki, K.5    Nemoto, H.6    Shimizu, H.7    Nagao, Y.8
  • 129
    • 0035249348 scopus 로고    scopus 로고
    • Acid-catalysed cyclo-aromatization of enediyne model compounds via enyne-allene intermediates
    • Suzuki, I.; Shigenaga, A.; Nemoto, H.; Shibuya, M. Acid-catalysed cyclo-aromatization of enediyne model compounds via enyne-allene intermediates. Heterocycles 2001, 54, 571-576.
    • (2001) Heterocycles , vol.54 , pp. 571-576
    • Suzuki, I.1    Shigenaga, A.2    Nemoto, H.3    Shibuya, M.4
  • 130
    • 2342451995 scopus 로고    scopus 로고
    • Synthesis and DNA damaging ability of enediyne model compounds possessing photo-triggering devices
    • Suzuki, I.; Uno, S.; Tsuchiya, Y.; Shigenaga, A.; Nemoto, H.; Shibuya, M. Synthesis and DNA damaging ability of enediyne model compounds possessing photo-triggering devices. Bioorg. Med. Chem. Lett. 2004, 14, 2959-2962.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 2959-2962
    • Suzuki, I.1    Uno, S.2    Tsuchiya, Y.3    Shigenaga, A.4    Nemoto, H.5    Shibuya, M.6
  • 132
    • 0028149664 scopus 로고
    • Photochemical analogue of the Bergman cycloaromatization reaction
    • Turro, N.J.; Evenzahav, A.; Nicolaou, K.C. Photochemical analogue of the Bergman cycloaromatization reaction. Tetrahedron Lett. 1994, 35, 8089-8092.
    • (1994) Tetrahedron Lett , vol.35 , pp. 8089-8092
    • Turro, N.J.1    Evenzahav, A.2    Nicolaou, K.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.