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Volumn 56, Issue 3, 2013, Pages 628-639

A remarkable series of vinblastine analogues displaying enhanced activity and an unprecedented tubulin binding steric tolerance: C20′ urea derivatives

Author keywords

[No Author keywords available]

Indexed keywords

TUBULIN; UREA DERIVATIVE; VINBLASTINE DERIVATIVE;

EID: 84872772908     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3015684     Document Type: Article
Times cited : (63)

References (43)
  • 1
    • 77957065406 scopus 로고
    • Therapeutic use of bisindole alkaloids from catharanthus
    • Review: In; Brossi, A. Suffness, M. Academic Press: San Diego, Vol.
    • Review: Neuss, N.; Neuss, M. N. Therapeutic use of bisindole alkaloids from catharanthus. In The Alkaloids; Brossi, A., Suffness, M., Eds.; Academic Press: San Diego, 1990; Vol. 37, pp 229-240.
    • (1990) The Alkaloids , vol.37 , pp. 229-240
    • Neuss, N.1    Neuss, M.N.2
  • 2
    • 77957080344 scopus 로고
    • Medicinal chemistry of bisindole alkaloids from catharanthus
    • Review: In; Brossi, A. Suffness, M. Academic Press: San Diego, Vol.
    • Review: Pearce, H. L. Medicinal chemistry of bisindole alkaloids from catharanthus. In The Alkaloids; Brossi, A., Suffness, M., Eds.; Academic Press: San Diego, 1990; Vol. 37, pp 145-204.
    • (1990) The Alkaloids , vol.37 , pp. 145-204
    • Pearce, H.L.1
  • 3
    • 77957095647 scopus 로고
    • Syntheses of vinblastine-type alkaloids
    • Review: In; Brossi, A. Suffness, M. Academic Press: San Diego, Vol.
    • Review: Kuehne, M. E.; Marko, I. Syntheses of vinblastine-type alkaloids. In The Alkaloids; Brossi, A., Suffness, M., Eds.; Academic Press: San Diego, 1990; Vol. 37, pp 77-132.
    • (1990) The Alkaloids , vol.37 , pp. 77-132
    • Kuehne, M.E.1    Marko, I.2
  • 4
    • 70449286540 scopus 로고
    • Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.). V. Preparation and characterization of alkaloids
    • Svoboda, G. H.; Nuess, N.; Gorman, M. Alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.). V. Preparation and characterization of alkaloids J. Am. Pharm. Assoc. Sci. Ed. 1959, 48, 659-666
    • (1959) J. Am. Pharm. Assoc. Sci. Ed. , vol.48 , pp. 659-666
    • Svoboda, G.H.1    Nuess, N.2    Gorman, M.3
  • 5
    • 84981860375 scopus 로고
    • Role of chance observations in chemotherapy: Vinca rosea
    • Noble, R. L.; Beer, C. T.; Cutts, J. H. Role of chance observations in chemotherapy: Vinca rosea Ann. N. Y. Acad. Sci. 1958, 76, 882-894
    • (1958) Ann. N. Y. Acad. Sci. , vol.76 , pp. 882-894
    • Noble, R.L.1    Beer, C.T.2    Cutts, J.H.3
  • 6
    • 26444618252 scopus 로고
    • Catharanthus roseus (Vinca rosea) - Importance and value of a chance observation
    • Noble, R. L. Catharanthus roseus (Vinca rosea)-importance and value of a chance observation Lloydia 1964, 27, 280-281
    • (1964) Lloydia , vol.27 , pp. 280-281
    • Noble, R.L.1
  • 7
    • 0034741810 scopus 로고    scopus 로고
    • Modifications in the "upper" velbenamine part of the Vinca alkaloids have major implications for tubulin interacting activities
    • Fahy, J. Modifications in the "upper" velbenamine part of the Vinca alkaloids have major implications for tubulin interacting activities Curr. Pharm. Des. 2001, 7, 1181-1197
    • (2001) Curr. Pharm. Des. , vol.7 , pp. 1181-1197
    • Fahy, J.1
  • 8
    • 0019130682 scopus 로고
    • Synthesis of the antitumor dimeric indole alkaloids from catharanthus species (vinblastine group)
    • Potier, P. Synthesis of the antitumor dimeric indole alkaloids from catharanthus species (vinblastine group) J. Nat. Prod. 1980, 43, 72-86
    • (1980) J. Nat. Prod. , vol.43 , pp. 72-86
    • Potier, P.1
  • 9
    • 0000018728 scopus 로고
    • Plant cell culture combined with chemistry: A powerful route to complex natural products
    • Kutney, J. P. Plant cell culture combined with chemistry: a powerful route to complex natural products Acc. Chem. Res. 1993, 26, 559-566
    • (1993) Acc. Chem. Res. , vol.26 , pp. 559-566
    • Kutney, J.P.1
  • 11
    • 0017172977 scopus 로고
    • Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloids
    • Langlois, N.; Gueritte, F.; Langlois, Y.; Potier, P. Application of a modification of the Polonovski reaction to the synthesis of vinblastine-type alkaloids J. Am. Chem. Soc. 1976, 98, 7017-7024
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 7017-7024
    • Langlois, N.1    Gueritte, F.2    Langlois, Y.3    Potier, P.4
  • 12
    • 0025980121 scopus 로고
    • Enantioselective syntheses of vinblastine, leurosidine, vincovaline, and 20′-epi-vincovaline
    • Kuehne, M. E.; Matson, P. A.; Bornmann, W. G. Enantioselective syntheses of vinblastine, leurosidine, vincovaline, and 20′-epi-vincovaline J. Org. Chem. 1991, 56, 513-528
    • (1991) J. Org. Chem. , vol.56 , pp. 513-528
    • Kuehne, M.E.1    Matson, P.A.2    Bornmann, W.G.3
  • 13
    • 0026550708 scopus 로고
    • A common intermediate providing syntheses of Ψ-tabersonine, coronaridine, iboxyphylline, ibophyllidine, vinamidine, and vinblastine
    • Bornmann, W. G.; Kuehne, M. E. A common intermediate providing syntheses of Ψ-tabersonine, coronaridine, iboxyphylline, ibophyllidine, vinamidine, and vinblastine J. Org. Chem. 1992, 57, 1752-1760
    • (1992) J. Org. Chem. , vol.57 , pp. 1752-1760
    • Bornmann, W.G.1    Kuehne, M.E.2
  • 16
    • 40149110727 scopus 로고    scopus 로고
    • Direct coupling of catharanthine and vindoline to provide vinblastine: Total synthesis of (+)- and ent -(-)-vinblastine
    • Ishikawa, H.; Colby, D. A.; Boger, D. L. Direct coupling of catharanthine and vindoline to provide vinblastine: total synthesis of (+)- and ent -(-)-vinblastine J. Am. Chem. Soc. 2008, 130, 420-421
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 420-421
    • Ishikawa, H.1    Colby, D.A.2    Boger, D.L.3
  • 17
  • 18
    • 33747600674 scopus 로고    scopus 로고
    • Total synthesis of (-)- and ent -(+)-vindoline and related alkaloids
    • Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. Total synthesis of (-)- and ent -(+)-vindoline and related alkaloids J. Am. Chem. Soc. 2006, 128, 10596-10612
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 10596-10612
    • Ishikawa, H.1    Elliott, G.I.2    Velcicky, J.3    Choi, Y.4    Boger, D.L.5
  • 21
    • 14844339765 scopus 로고    scopus 로고
    • Total synthesis of natural (-)- and ent -(+)-4-desacetoxy-6,7- dihydrovindorosine and natural and ent -minovine: Oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction
    • Yuan, Z.; Ishikawa, H.; Boger, D. L. Total synthesis of natural (-)- and ent -(+)-4-desacetoxy-6,7-dihydrovindorosine and natural and ent -minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction Org. Lett. 2005, 7, 741-744
    • (2005) Org. Lett. , vol.7 , pp. 741-744
    • Yuan, Z.1    Ishikawa, H.2    Boger, D.L.3
  • 23
    • 77953636730 scopus 로고    scopus 로고
    • Total synthesis and evaluation of a key series of C5-substituted vinblastine derivatives
    • Va, P.; Campbell, E. L.; Robertson, W. M.; Boger, D. L. Total synthesis and evaluation of a key series of C5-substituted vinblastine derivatives J. Am. Chem. Soc. 2010, 132, 8489-8495
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 8489-8495
    • Va, P.1    Campbell, E.L.2    Robertson, W.M.3    Boger, D.L.4
  • 24
    • 77957154690 scopus 로고    scopus 로고
    • Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues
    • Sasaki, Y.; Kato, D.; Boger, D. L. Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues J. Am. Chem. Soc. 2010, 132, 13533-13544
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 13533-13544
    • Sasaki, Y.1    Kato, D.2    Boger, D.L.3
  • 25
    • 77949853491 scopus 로고    scopus 로고
    • Asymmetric total synthesis of vindoline
    • Kato, D.; Sasaki, Y.; Boger, D. L. Asymmetric total synthesis of vindoline J. Am. Chem. Soc. 2010, 132, 3685-3687
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 3685-3687
    • Kato, D.1    Sasaki, Y.2    Boger, D.L.3
  • 26
    • 77958045870 scopus 로고    scopus 로고
    • Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: Preparation and evaluation of a key series of vinblastine analogues
    • Tam, A.; Gotoh, H.; Robertson, W. M.; Boger, D. L. Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: preparation and evaluation of a key series of vinblastine analogues Bioorg. Med. Chem. Lett. 2010, 20, 6408-6410
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 6408-6410
    • Tam, A.1    Gotoh, H.2    Robertson, W.M.3    Boger, D.L.4
  • 27
    • 83455258222 scopus 로고    scopus 로고
    • 10′-Fluorovinblastine and 10′-fluorovincristine: Synthesis of a key series of modified Vinca alkaloids
    • Gotoh, H.; Duncan, K. K.; Robertson, W. M.; Boger, D. L. 10′-Fluorovinblastine and 10′-fluorovincristine: synthesis of a key series of modified Vinca alkaloids ACS Med. Chem. Lett. 2011, 2, 948-952
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 948-952
    • Gotoh, H.1    Duncan, K.K.2    Robertson, W.M.3    Boger, D.L.4
  • 28
    • 84865120407 scopus 로고    scopus 로고
    • New insights into the mechanism and an expanded scope of the Fe(III)-mediated vinblastine coupling reaction
    • Gotoh, H.; Sears, J. E.; Eschenmoser, A.; Boger, D. L. New insights into the mechanism and an expanded scope of the Fe(III)-mediated vinblastine coupling reaction J. Am. Chem. Soc. 2012, 134, 13240-13243
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 13240-13243
    • Gotoh, H.1    Sears, J.E.2    Eschenmoser, A.3    Boger, D.L.4
  • 29
    • 84858665556 scopus 로고    scopus 로고
    • 4-mediated additions to unactivated alkenes: Synthesis of novel 20′-vinblastine analogues
    • 4-mediated additions to unactivated alkenes: synthesis of novel 20′-vinblastine analogues Org. Lett. 2012, 14, 1428-1431
    • (2012) Org. Lett. , vol.14 , pp. 1428-1431
    • Leggans, E.K.1    Barker, T.J.2    Duncan, K.K.3    Boger, D.L.4
  • 30
    • 84865431754 scopus 로고    scopus 로고
    • 4-mediated free radical hydrofluorination of unactivated alkenes
    • 4-mediated free radical hydrofluorination of unactivated alkenes J. Am. Chem. Soc. 2012, 134, 13588-13591
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 13588-13591
    • Barker, T.J.1    Boger, D.L.2
  • 31
    • 0001278411 scopus 로고
    • Total synthesis of azafluoranthine alkaloids: Rufescine and imelutine
    • Boger, D. L.; Brotherton, C. E. Total synthesis of azafluoranthine alkaloids: rufescine and imelutine J. Org. Chem. 1984, 49, 4050-4055
    • (1984) J. Org. Chem. , vol.49 , pp. 4050-4055
    • Boger, D.L.1    Brotherton, C.E.2
  • 32
    • 77957030571 scopus 로고
    • Functional hot spot at the C-20′ position of vinblastine
    • In; Brossi, A. Suffness, M. Academic Press: San Diego, Vol.
    • Borman, L. S.; Kuehne, M. E. Functional hot spot at the C-20′ position of vinblastine. In The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic Press: San Diego, 1990; Vol. 37, pp 133-144.
    • (1990) The Alkaloids , vol.37 , pp. 133-144
    • Borman, L.S.1    Kuehne, M.E.2
  • 34
    • 0017334529 scopus 로고
    • Alkaloids of Vinca rosea L. (Catharanthus roseus G. Don). 38. 4′-dehydrated derivatives
    • Miller, J. C.; Gutowski, G. E.; Poore, G. A.; Boder, G. B. Alkaloids of Vinca rosea L. (Catharanthus roseus G. Don). 38. 4′-dehydrated derivatives J. Med. Chem. 1977, 20, 409-413
    • (1977) J. Med. Chem. , vol.20 , pp. 409-413
    • Miller, J.C.1    Gutowski, G.E.2    Poore, G.A.3    Boder, G.B.4
  • 36
    • 84873891558 scopus 로고
    • Chem. Abstr. 1978, 89, 129778.
    • (1978) Chem. Abstr. , vol.89 , pp. 129778
  • 38
    • 84885458833 scopus 로고
    • Chem. Abstr. 1982, 97, 163310).
    • (1982) Chem. Abstr. , vol.97 , pp. 163310
  • 39
    • 0036086184 scopus 로고    scopus 로고
    • Novel aspects of natural and modified Vinca alkaloids
    • Review of superacid functionalization
    • Review of superacid functionalization: Duflos, A.; Kruczynski, A.; Baret, J.-M. Novel aspects of natural and modified Vinca alkaloids. Curr. Med. Chem., Anti-Cancer Agents 2002, 2, 55-75.
    • (2002) Curr. Med. Chem., Anti-Cancer Agents , vol.2 , pp. 55-75
    • Duflos, A.1    Kruczynski, A.2    Baret, J.-M.3
  • 42
    • 84862296187 scopus 로고    scopus 로고
    • Structural modifications that alter the P-glycoprotein efflux properties of compounds
    • Hitchcock, S. A. Structural modifications that alter the P-glycoprotein efflux properties of compounds J. Med. Chem. 2012, 55, 4877-4895
    • (2012) J. Med. Chem. , vol.55 , pp. 4877-4895
    • Hitchcock, S.A.1
  • 43
    • 0017736254 scopus 로고
    • Correlation of biologic data with physicochemical properties among the Vinca alkaloids and their congeners
    • Owellen, R. J.; Donigian, D. W.; Hartke, C. A.; Hains, F. O. Correlation of biologic data with physicochemical properties among the Vinca alkaloids and their congeners Biochem. Pharmacol. 1977, 26, 1213-1219
    • (1977) Biochem. Pharmacol. , vol.26 , pp. 1213-1219
    • Owellen, R.J.1    Donigian, D.W.2    Hartke, C.A.3    Hains, F.O.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.