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Volumn 57, Issue 12, 2014, Pages 5085-5093

Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: Design, synthesis, and pharmacokinetic studies

Author keywords

[No Author keywords available]

Indexed keywords

13 DEBROMO 13 TRIFLUOROMETHYL AGELASTATIN A; AGELASTATIN A; AGELASTATIN DERIVATIVE; ALKALOID DERIVATIVE; ANTILEUKEMIC AGENT; FLUORINE DERIVATIVE; IMIDAZOLE DERIVATIVE; NATURAL PRODUCT; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84903523658     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4016922     Document Type: Article
Times cited : (36)

References (32)
  • 1
    • 84903514325 scopus 로고    scopus 로고
    • Leukemia & Lymphoma Society
    • Leukemia & Lymphoma Society, 2012. http://www.lls.org/ diseaseinformation/getinformationsupport/factsstatistics/.
    • (2012)
  • 3
    • 84862586155 scopus 로고    scopus 로고
    • Gene immunotherapy of chronic lymphocytic leukemia: A phase i study of intranodally injected adenovirus expressing a chimeric CD154 molecule
    • Castro, J. E.; Melo-Cardenas, J.; Urquiza, M.; Barajas-Gamboa, J. S.; Pakbaz, R. S.; Kipps, T. J. Gene immunotherapy of chronic lymphocytic leukemia: a phase I study of intranodally injected adenovirus expressing a chimeric CD154 molecule Cancer Res. 2012, 72, 2937-2948
    • (2012) Cancer Res. , vol.72 , pp. 2937-2948
    • Castro, J.E.1    Melo-Cardenas, J.2    Urquiza, M.3    Barajas-Gamboa, J.S.4    Pakbaz, R.S.5    Kipps, T.J.6
  • 4
    • 0034009217 scopus 로고    scopus 로고
    • Novel mechanisms of drug resistance in leukemia
    • Ross, D. D. Novel mechanisms of drug resistance in leukemia Leukemia 2000, 14, 467-473
    • (2000) Leukemia , vol.14 , pp. 467-473
    • Ross, D.D.1
  • 5
    • 0027170397 scopus 로고
    • Agelastatin A, A new skeleton cytotoxic alkaloid of the oroidin family - Isolation from the Axinellid sponge Agelas dendromorpha of the Coral Sea
    • D'Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. Agelastatin A, A new skeleton cytotoxic alkaloid of the oroidin family-isolation from the Axinellid sponge Agelas dendromorpha of the Coral Sea J. Chem. Soc. Chem. Commun. 1993, 1305-1306
    • (1993) J. Chem. Soc. Chem. Commun. , pp. 1305-1306
    • D'Ambrosio, M.1    Guerriero, A.2    Debitus, C.3    Ribes, O.4    Pusset, J.5    Leroy, S.6    Pietra, F.7
  • 6
    • 0028116772 scopus 로고
    • Conformational preferences and absolute configuration of agelastatin A, A cytotoxic alkaloid of the Axinellid sponge Agelas dendromorpha from the Coral Sea, via combined molecular modeling, NMR, and exciton splitting for diamide and hydroxyamide derivatives
    • D'Ambrosio, M.; Guerriero, A.; Chiasera, G.; Pietra, F. Conformational preferences and absolute configuration of agelastatin A, A cytotoxic alkaloid of the Axinellid sponge Agelas dendromorpha from the Coral Sea, via combined molecular modeling, NMR, and exciton splitting for diamide and hydroxyamide derivatives Helv. Chim. Acta 1994, 77, 1895-1902
    • (1994) Helv. Chim. Acta , vol.77 , pp. 1895-1902
    • D'Ambrosio, M.1    Guerriero, A.2    Chiasera, G.3    Pietra, F.4
  • 7
    • 0031886176 scopus 로고    scopus 로고
    • Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A
    • Hong, T. W.; Jimenez, D. R.; Molinski, T. F. Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A J. Nat. Prod. 1998, 61, 158-161
    • (1998) J. Nat. Prod. , vol.61 , pp. 158-161
    • Hong, T.W.1    Jimenez, D.R.2    Molinski, T.F.3
  • 8
    • 80052065246 scopus 로고    scopus 로고
    • Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids
    • Al-Mourabit, A.; Zancanella, M. A.; Tilvi, S.; Romo, D. Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids Nat. Prod. Rep. 2011, 28, 1229-1260
    • (2011) Nat. Prod. Rep. , vol.28 , pp. 1229-1260
    • Al-Mourabit, A.1    Zancanella, M.A.2    Tilvi, S.3    Romo, D.4
  • 9
    • 0032748434 scopus 로고    scopus 로고
    • Total synthesis of the antitumor marine sponge alkaloid agelastatin A
    • Stien, D.; Anderson, G. T.; Chase, C. E.; Koh, Y.-H.; Weinreb, S. M. Total synthesis of the antitumor marine sponge alkaloid agelastatin A J. Am. Chem. Soc. 1999, 121 (41) 9574-9579
    • (1999) J. Am. Chem. Soc. , vol.121 , Issue.41 , pp. 9574-9579
    • Stien, D.1    Anderson, G.T.2    Chase, C.E.3    Koh, Y.-H.4    Weinreb, S.M.5
  • 10
    • 84885145705 scopus 로고    scopus 로고
    • A short total synthesis of the marine sponge pyrrole-2-aminoimidazole alkaloid (±)-agelastatin A
    • Duspara, P. A.; Batey, R. A. A short total synthesis of the marine sponge pyrrole-2-aminoimidazole alkaloid (±)-agelastatin A Angew. Chem.. Int. Ed. 2013, 52, 10862-10866
    • (2013) Angew. Chem.. Int. Ed. , vol.52 , pp. 10862-10866
    • Duspara, P.A.1    Batey, R.A.2
  • 11
    • 84863694084 scopus 로고    scopus 로고
    • Bioinspired total synthesis of agelastatin A
    • Reyes, J. C. P.; Romo, D. Bioinspired total synthesis of agelastatin A Angew. Chem., Int. Ed. 2012, 51, 6870-6873
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 6870-6873
    • Reyes, J.C.P.1    Romo, D.2
  • 12
    • 4043079398 scopus 로고    scopus 로고
    • New total synthesis of the marine antitumor alkaloid (±)- agelastatin A
    • Domostoj, M. M.; Irving, E.; Scheinmann, F.; Hale, K. J. New total synthesis of the marine antitumor alkaloid (±)-agelastatin A Org. Lett. 2004, 6, 2615-2618
    • (2004) Org. Lett. , vol.6 , pp. 2615-2618
    • Domostoj, M.M.1    Irving, E.2    Scheinmann, F.3    Hale, K.J.4
  • 13
    • 79952607810 scopus 로고    scopus 로고
    • Total synthesis of all (-)-agelastatin alkaloids
    • Movassaghi, M.; Siegel, D. S.; Han, S. Total synthesis of all (-)-agelastatin alkaloids Chem. Sci. 2010, 1, 561-566
    • (2010) Chem. Sci. , vol.1 , pp. 561-566
    • Movassaghi, M.1    Siegel, D.S.2    Han, S.3
  • 14
    • 70349786454 scopus 로고    scopus 로고
    • A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A
    • Wehn, P. M.; Du Bois, J. A stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A Angew. Chem.. Int. Ed. 2009, 48, 3802-3805
    • (2009) Angew. Chem.. Int. Ed. , vol.48 , pp. 3802-3805
    • Wehn, P.M.1    Du Bois, J.2
  • 15
    • 78649809107 scopus 로고    scopus 로고
    • Recent advances in the total synthesis of agelastatins
    • Dong, G. Recent advances in the total synthesis of agelastatins Pure Appl. Chem. 2010, 82, 2231-2314
    • (2010) Pure Appl. Chem. , vol.82 , pp. 2231-2314
    • Dong, G.1
  • 18
  • 19
    • 84879863287 scopus 로고    scopus 로고
    • An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: Chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses
    • Li, Z.; Shigeoka, D.; Caulfield, T. R.; Kawachi, T.; Qiu, Y.; Kamon, T.; Arai, M.; Tun, H. W.; Yoshimitsu, T. An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses Med. Chem. Commun. 2013, 4, 1093-1098
    • (2013) Med. Chem. Commun. , vol.4 , pp. 1093-1098
    • Li, Z.1    Shigeoka, D.2    Caulfield, T.R.3    Kawachi, T.4    Qiu, Y.5    Kamon, T.6    Arai, M.7    Tun, H.W.8    Yoshimitsu, T.9
  • 21
    • 83055177179 scopus 로고    scopus 로고
    • Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis
    • Nagib, D. A.; MacMillan, D. W. C. Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis Nature 2011, 480, 224-228
    • (2011) Nature , vol.480 , pp. 224-228
    • Nagib, D.A.1    Macmillan, D.W.C.2
  • 24
    • 0026750647 scopus 로고
    • The human hepatic cytochromes P450 involved in drug metabolism
    • Wrighton, S. A.; Stevens, J. C. The human hepatic cytochromes P450 involved in drug metabolism Crit. Rev. Toxicol. 1992, 22, 1-21
    • (1992) Crit. Rev. Toxicol. , vol.22 , pp. 1-21
    • Wrighton, S.A.1    Stevens, J.C.2
  • 27
    • 4243664295 scopus 로고
    • A Survey of Hammett substituent constants and resonance and field parameters
    • Hansch, C.; Leo, A.; Taft, R. W. A Survey of Hammett substituent constants and resonance and field parameters Chem. Rev. 1991, 97, 165-195
    • (1991) Chem. Rev. , vol.97 , pp. 165-195
    • Hansch, C.1    Leo, A.2    Taft, R.W.3
  • 30
    • 50849150452 scopus 로고
    • Steric effects: A critical examination of the Taft steric parameters. Definition of a revised, broader and homogeneous scale. Extension to highly congested alkyl groups
    • MacPhee, J. A.; Panaye, A.; Dubois, J.-E. Steric effects: A critical examination of the Taft steric parameters. Definition of a revised, broader and homogeneous scale. Extension to highly congested alkyl groups Tetrahedron 1978, 34 (24) 3553-3562
    • (1978) Tetrahedron , vol.34 , Issue.24 , pp. 3553-3562
    • Macphee, J.A.1    Panaye, A.2    Dubois, J.-E.3
  • 31
    • 70349786454 scopus 로고    scopus 로고
    • A Stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A
    • Wehn, P. M.; Du Bois, J. A Stereoselective synthesis of the bromopyrrole natural product (-)-agelastatin A Angew. Chem. Int. Ed. 2009, 48, 3802-3805
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3802-3805
    • Wehn, P.M.1    Du Bois, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.