메뉴 건너뛰기




Volumn 53, Issue 21, 2010, Pages 7843-7851

Synthetic analogues of the microtubule-stabilizing sponge alkaloid ceratamine A are more active than the natural product

Author keywords

[No Author keywords available]

Indexed keywords

2 (DIMETHYLAMINO) 4 (4 METHOXY 3,5 DIMETHYLBENZYL) 6 METHYLIMIDAZO[4,5 D]AZEPIN 5(6H) ONE; 2 [1 [(BENZYLOXY)METHYL] 2 CHLORO 4 FORMYL 1H IMIDAZOL 5 YL] 3 (4 METHOXY 3,5 DIMETHYLPHENYL) N METHYLACRYLAMIDE; 2 AMINO 3 [(BENZYLOXY)METHYL] 4 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 6 METHYL 4,6 DIHYDROIMIDAZO[4,5 D]AZEPIN 5(3H) ONE; 2 AMINO 3 [(BENZYLOXY)METHYL] 4 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 6 METHYL 4,6,7,8 TETRAHYDROIMIDAZO[4,5 D]AZEPIN 5(3H) ONE; 2 AMINO 4 (4 METHOXY 3,5 DIMETHYLBENZYL) 6 METHYL 4,6,7,8 TETRAHYDROIMIDAZO[4,5 D]AZEPIN 5(3H) ONE; 2 AMINO 4 (4 METHOXY 3,5 DIMETHYLBENZYL) 6 METHYLIMIDAZO [4,5 D]AZEPIN 5(6H) ONE; 2 BROMO 3 (4 METHOXY 3,5 DIMETHYLPHENYL) N METHYLACRYLAMIDE; 2,2,2 TRIFLUORO N [8 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 1,6 DIMETHYL 7 OXO 1,6,7,8 TETRAHYDROIMIDAZO[4,5 D]AZEPIN-2 YL] N METHYLACETAMIDE; 2-(1 [(BENZYLOXY)METHYL] 4 (2 BROMOVINYL) 2 CHLORO 1H IMIDAZOL 5 YL) 3 (4 METHOXY 3,5 DIMETHYLPHENYL) N METHYLACRYLAMIDE; 3 [(BENZYLOXY)METHYL] 2 CHLORO 4 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 6 METHYL 4,6 DIHYDROIMIDAZO[4,5 D]AZEPIN 5(3H) ONE; 3 [(BENZYLOXY)METHYL] 4 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 6 METHYL 2 (METHYLAMINO) 4,6,7,8 TETRAHYDROIMIDAZO[4,5 D] AZEPIN 5(3H) ONE; 4 (4 METHOXY 3,5 DIMETHYLBENZYL) 6 METHYL 2 (METHYLAMINO) 4,6,7,8 TETRAHYDROIMIDAZO[4,5 D]AZEPIN 5(3H) ONE; 4 (4 METHOXY 3,5 DIMETHYLBENZYL) 6 METHYL 2 (METHYLAMINO) IMIDAZO[4,5 D]AZEPIN 5(6H) ONE; 4 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 6 METHYL 2 (METHYLAMINO) 4,6,7,8 TETRAHYDROIMIDAZO[4,5 D]AZEPIN 5(3H) ONE; 7 HYDROXY 4 (4 METHOXY 3,5 DIMETHYLBENZOYL) 6 METHYL 2 (METHYLAMINO)IMIDAZO[4,5 D]AZEPIN 5(6H) ONE; 8 HYDROXY 4 (4 METHOXY 3,5 DIMETHYLBENZOYL) 6 METHYL 2 (METHYLAMINO)IMIDAZO[4,5 D]AZEPIN 5(6H) ONE; ALKALOID; BROMINE; CERATAMINE A; DESBROMOCERATAMINE A; METHYL GROUP; N [1 [(BENZYLOXY)METHYL] 8 (4 METHOXY 3,5 DIMETHYLBENZYLIDENE) 6 METHYL 7 OXO 1,6,7,8 TETRAHYDROIMIDAZO[4,5 D]AZEPIN 2 YL) N METHYLFORMAMIDE; NATURAL PRODUCT; NITROGEN; UNCLASSIFIED DRUG;

EID: 78149238232     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101012q     Document Type: Article
Times cited : (18)

References (19)
  • 2
    • 0002776842 scopus 로고
    • Synthesis of the imidazo[4,5-d]azepine ring system
    • Synthetic compounds containing partially oxidized forms of the ring system were first reported in
    • Synthetic compounds containing partially oxidized forms of the ring system were first reported in Waly, M. A. Synthesis of the imidazo[4,5-d]azepine ring system Prakt. Chem. 1994, 336, 86-88
    • (1994) Prakt. Chem. , vol.336 , pp. 86-88
    • Waly, M.A.1
  • 3
    • 17144385513 scopus 로고    scopus 로고
    • Ceratamines, structurally simple microtubule-stabilizing antimitotic agents with unusual cellular effects
    • Karjala, G.; Chan, Q.; Manzo, E.; Andersen, R. J.; Roberge, M. Ceratamines, structurally simple microtubule-stabilizing antimitotic agents with unusual cellular effects Cancer Res. 2005, 65, 3040-3043
    • (2005) Cancer Res. , vol.65 , pp. 3040-3043
    • Karjala, G.1    Chan, Q.2    Manzo, E.3    Andersen, R.J.4    Roberge, M.5
  • 4
    • 50349084470 scopus 로고    scopus 로고
    • Ixabepilone: A new antimitotic for the treatment of metastatic breast cancer
    • Bhushan, S.; Walko, C. M. Ixabepilone: A new antimitotic for the treatment of metastatic breast cancer Ann. Pharmacother. 2008, 42, 1252-1261
    • (2008) Ann. Pharmacother. , vol.42 , pp. 1252-1261
    • Bhushan, S.1    Walko, C.M.2
  • 5
    • 45549107292 scopus 로고    scopus 로고
    • Synthesis of antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A
    • Nodwell, M.; Riffell, J. L.; Roberge, M.; Andersen, R. J. Synthesis of antimitotic analogs of the microtubule stabilizing sponge alkaloid ceratamine A Org. Lett. 2008, 10, 1051-1054
    • (2008) Org. Lett. , vol.10 , pp. 1051-1054
    • Nodwell, M.1    Riffell, J.L.2    Roberge, M.3    Andersen, R.J.4
  • 6
    • 64549131343 scopus 로고    scopus 로고
    • Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues
    • Nodwell, M; Pereira, A.; Riffell, C.; Zimmerman, C.; Patrick, B. O.; Roberge, M.; Andersen, R. J. Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues J. Org. Chem. 2009, 74, 995-1006
    • (2009) J. Org. Chem. , vol.74 , pp. 995-1006
    • Nodwell, M.1    Pereira, A.2    Riffell, C.3    Zimmerman, C.4    Patrick, B.O.5    Roberge, M.6    Andersen, R.J.7
  • 7
    • 33847087228 scopus 로고
    • Steric Effects. A Study of a Rationally Designed System
    • Bott, G.; Field, L. D.; Sternhell, S. Steric Effects. A Study of a Rationally Designed System J. Am. Chem. Soc. 1980, 102, 5618-5626
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5618-5626
    • Bott, G.1    Field, L.D.2    Sternhell, S.3
  • 8
    • 0037454332 scopus 로고    scopus 로고
    • (Z)-α-Haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates
    • Barma, D. K.; Kundu, A.; Zhang, H.; Mioskowski, C.; Falck, J. R. (Z)-α-Haloacrylates: an exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates J. Am. Chem. Soc. 2003, 125, 3218-3219
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 3218-3219
    • Barma, D.K.1    Kundu, A.2    Zhang, H.3    Mioskowski, C.4    Falck, J.R.5
  • 9
    • 0001647908 scopus 로고
    • A stereoselective synthesis of (Z)-1-iodo-1-alkenes
    • Stork, G; Zhao, K. A stereoselective synthesis of (Z)-1-iodo-1-alkenes Tetrahedron Lett. 1989, 30, 2173-2174
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2173-2174
    • Stork, G.1    Zhao, K.2
  • 10
    • 0142106421 scopus 로고    scopus 로고
    • Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides
    • Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides Org. Lett. 2003, 5, 3667-3669
    • (2003) Org. Lett. , vol.5 , pp. 3667-3669
    • Jiang, L.1    Job, G.E.2    Klapars, A.3    Buchwald, S.L.4
  • 11
    • 0038579438 scopus 로고    scopus 로고
    • Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
    • Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions J. Am. Chem. Soc. 2003, 125, 6653-6655
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6653-6655
    • Huang, X.1    Anderson, K.W.2    Zim, D.3    Jiang, L.4    Klapars, A.5    Buchwald, S.L.6
  • 12
    • 33947416063 scopus 로고    scopus 로고
    • Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters
    • Billingsley, K.; Buchwald, S. L. Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters J. Am. Chem. Soc. 2007, 129, 3358-3366
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 3358-3366
    • Billingsley, K.1    Buchwald, S.L.2
  • 13
    • 66149148661 scopus 로고    scopus 로고
    • A direct and efficient total synthesis of the tubulin-binding agents ceratamines A and B; Use of IBX for a remarkable heterocyclic dehydrogenation
    • Coleman, R. S.; Campbell, E. L.; Carper, D. J. A direct and efficient total synthesis of the tubulin-binding agents ceratamines A and B; use of IBX for a remarkable heterocyclic dehydrogenation Org. Lett. 2009, 11, 2133-2136
    • (2009) Org. Lett. , vol.11 , pp. 2133-2136
    • Coleman, R.S.1    Campbell, E.L.2    Carper, D.J.3
  • 15
    • 7744233719 scopus 로고    scopus 로고
    • Stuck in division or passing through: What happens when cells cannot satisfy the spindle assembly checkpoint
    • Rieder, C. L.; Maiato, H. Stuck in division or passing through: What happens when cells cannot satisfy the spindle assembly checkpoint Dev. Cell 2004, 7, 637-651
    • (2004) Dev. Cell , vol.7 , pp. 637-651
    • Rieder, C.L.1    Maiato, H.2
  • 16
    • 0033546262 scopus 로고    scopus 로고
    • A user-friendly entry to 2-iodoxybenzoic acid (IBX)
    • Frigerio, M.; Santagostino, M.; Sputore, S. A user-friendly entry to 2-iodoxybenzoic acid (IBX) J. Org. Chem. 1999, 64, 4537-4538
    • (1999) J. Org. Chem. , vol.64 , pp. 4537-4538
    • Frigerio, M.1    Santagostino, M.2    Sputore, S.3
  • 17
    • 70349270650 scopus 로고    scopus 로고
    • Effects of chemical manipulation of mitotic arrest and slippage on cancer cell survival and proliferation
    • Riffell, J. L.; Zimmerman, C.; Khong, A.; McHardy, L. M.; Roberge, M. Effects of chemical manipulation of mitotic arrest and slippage on cancer cell survival and proliferation Cell Cycle 2009, 8, 1-14
    • (2009) Cell Cycle , vol.8 , pp. 1-14
    • Riffell, J.L.1    Zimmerman, C.2    Khong, A.3    McHardy, L.M.4    Roberge, M.5
  • 19
    • 0034665125 scopus 로고    scopus 로고
    • Cell-based screen for antimitotic agents and identification of analogues of rhizoxin, eleutherobin, and paclitaxel in natural extracts
    • Roberge, M.; Cinel, B.; Anderson, H. J.; Lim, L.; Jiang, X.; Xu, L.; Bigg, C. M.; Kelly, M. T.; Andersen, R. J. Cell-based screen for antimitotic agents and identification of analogues of rhizoxin, eleutherobin, and paclitaxel in natural extracts Cancer Res. 2000, 60, 5052-5058
    • (2000) Cancer Res. , vol.60 , pp. 5052-5058
    • Roberge, M.1    Cinel, B.2    Anderson, H.J.3    Lim, L.4    Jiang, X.5    Xu, L.6    Bigg, C.M.7    Kelly, M.T.8    Andersen, R.J.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.