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Volumn 2, Issue 2, 2007, Pages 317-321

Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis

Author keywords

[No Author keywords available]

Indexed keywords

MONASTROL; EG5 PROTEIN, XENOPUS; KINESIN; PYRIMIDINE DERIVATIVE; THIOKETONE; UNCLASSIFIED DRUG; XENOPUS PROTEIN;

EID: 34347250848     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2006.436     Document Type: Article
Times cited : (36)

References (31)
  • 1
    • 0033615357 scopus 로고    scopus 로고
    • Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen
    • Mayer, T.U. et al. Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen. Science 286 971-974 (1999).
    • (1999) Science , vol.286 , pp. 971-974
    • Mayer, T.U.1
  • 2
    • 0036909567 scopus 로고    scopus 로고
    • Small molecules, big impact: A history of chemical inhibitors and the cytoskeleton
    • Peterson, J.R. & Mitchison, T.J. Small molecules, big impact: A history of chemical inhibitors and the cytoskeleton. Chem. Biol. 9, 1275-1285 (2002).
    • (2002) Chem. Biol , vol.9 , pp. 1275-1285
    • Peterson, J.R.1    Mitchison, T.J.2
  • 3
    • 22144463476 scopus 로고    scopus 로고
    • Development and biological evaluation of potent and specific inhibitors of mitotic kinesin Eg5
    • Gartner, M. et al. Development and biological evaluation of potent and specific inhibitors of mitotic kinesin Eg5. ChemBioChem 6 1173-1177 (2005).
    • (2005) ChemBioChem , vol.6 , pp. 1173-1177
    • Gartner, M.1
  • 4
    • 33646481056 scopus 로고    scopus 로고
    • Inhibitors of mitotic kinesins: Next-generation antimitotics
    • Sarli, V. & Giannis, A. Inhibitors of mitotic kinesins: Next-generation antimitotics. ChemMedChem 1, 293-298 (2006).
    • (2006) ChemMedChem , vol.1 , pp. 293-298
    • Sarli, V.1    Giannis, A.2
  • 6
    • 0011932271 scopus 로고    scopus 로고
    • Loupy, A, ed, 2nd edn, Wiley-VCH, Weinheim, Germany
    • Loupy, A. (ed) Microwaves in Organic Synthesis 2nd edn. (Wiley-VCH, Weinheim, Germany, 2006).
    • (2006) Microwaves in Organic Synthesis
  • 7
    • 33644853780 scopus 로고    scopus 로고
    • The impact of microwave synthesis on drug discovery
    • Kappe, C.O. & Dallinger, D. The impact of microwave synthesis on drug discovery. Nat. Rev. Drug Discov. 5, 51-64 (2006).
    • (2006) Nat. Rev. Drug Discov , vol.5 , pp. 51-64
    • Kappe, C.O.1    Dallinger, D.2
  • 8
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 43, 6250-6284 (2004).
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 6250-6284
    • Kappe, C.O.1
  • 9
    • 4544275755 scopus 로고    scopus 로고
    • Recent advances in microwave-assisted synthesis
    • Hayes, B.L. Recent advances in microwave-assisted synthesis. Aldrichim. Acta 37, 66-77 (2004).
    • (2004) Aldrichim. Acta , vol.37 , pp. 66-77
    • Hayes, B.L.1
  • 10
    • 0000176059 scopus 로고
    • Aldehyde-urea derivatives of aceto- and oxaloacetic acids
    • Biginelli, P. Aldehyde-urea derivatives of aceto- and oxaloacetic acids. Gazz. Chim. Ital. 23, 360-413 (1893).
    • (1893) Gazz. Chim. Ital , vol.23 , pp. 360-413
    • Biginelli, P.1
  • 11
    • 0034518876 scopus 로고    scopus 로고
    • Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog
    • Kappe, C.O. Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc. Chem. Res. 33, 879-888 (2000).
    • (2000) Acc. Chem. Res , vol.33 , pp. 879-888
    • Kappe, C.O.1
  • 12
    • 0034519777 scopus 로고    scopus 로고
    • Biologically active dihydropyrimidones of the Biginelli-type. A literature survey
    • Kappe, C.O. Biologically active dihydropyrimidones of the Biginelli-type. A literature survey. Eur. J. Med. Chem. 35, 1043-1052 (2000).
    • (2000) Eur. J. Med. Chem , vol.35 , pp. 1043-1052
    • Kappe, C.O.1
  • 13
    • 0001260317 scopus 로고    scopus 로고
    • Automated library generation using sequential microwave-assisted chemistry. Application toward the Biginelli multicomponent condensation
    • Stadler, A. & Kappe, C.O. Automated library generation using sequential microwave-assisted chemistry. Application toward the Biginelli multicomponent condensation. J. Comb. Chem. 3, 624-630 (2001).
    • (2001) J. Comb. Chem , vol.3 , pp. 624-630
    • Stadler, A.1    Kappe, C.O.2
  • 14
    • 0037136153 scopus 로고    scopus 로고
    • Improved synthesis and preparative scale resolution of racemic monastrol
    • Dondoni, A., Massi, A. & Sabbatini, S. Improved synthesis and preparative scale resolution of racemic monastrol. Tetrahedron Lett. 43, 5013-5916 (2002).
    • (2002) Tetrahedron Lett , vol.43 , pp. 5013-5916
    • Dondoni, A.1    Massi, A.2    Sabbatini, S.3
  • 15
    • 0034708729 scopus 로고    scopus 로고
    • X-ray structure, conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol
    • Kappe, C.O., Shishkin, O.V., Uray, G. & Verdino, P. X-ray structure, conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol. Tetrahedron 56, 1859-1862 (2000).
    • (2000) Tetrahedron , vol.56 , pp. 1859-1862
    • Kappe, C.O.1    Shishkin, O.V.2    Uray, G.3    Verdino, P.4
  • 16
    • 1242318623 scopus 로고    scopus 로고
    • A remarkable rate acceleration of the one-pot three-component cyclocondensation reaction at room temperature: An expedient synthesis of mitotic kinesin Eg5 inhibitor monastrol
    • Bose, D.S., Kumar, R.K. & Fatima, L. A remarkable rate acceleration of the one-pot three-component cyclocondensation reaction at room temperature: An expedient synthesis of mitotic kinesin Eg5 inhibitor monastrol. Synlett 279-282 (2004).
    • (2004) Synlett , vol.279-282
    • Bose, D.S.1    Kumar, R.K.2    Fatima, L.3
  • 17
    • 23044493101 scopus 로고    scopus 로고
    • De, S.K. & Gibbs, R.A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Synthesis 1748-1750 (2005).
    • De, S.K. & Gibbs, R.A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Synthesis 1748-1750 (2005).
  • 18
    • 33745752826 scopus 로고    scopus 로고
    • Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines, monastrol, oxo-monastrol and oxygenated analogues
    • Russowsky, D. et al. Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines, monastrol, oxo-monastrol and oxygenated analogues. Bioorg. Chem. 34, 173-182 (2006).
    • (2006) Bioorg. Chem , vol.34 , pp. 173-182
    • Russowsky, D.1
  • 19
    • 20144371079 scopus 로고    scopus 로고
    • Pasha, M.A., Swamy, N.R. & Jayashankara, V.P. One pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/-thiones catalysed by zinc chloride: An improved procedure for the Biginelli reaction using microwaves under solvent free condition. Indian J. Chem., Sect B 44B, 823-826 (2005).
    • Pasha, M.A., Swamy, N.R. & Jayashankara, V.P. One pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/-thiones catalysed by zinc chloride: An improved procedure for the Biginelli reaction using microwaves under solvent free condition. Indian J. Chem., Sect B 44B, 823-826 (2005).
  • 21
    • 4544226835 scopus 로고    scopus 로고
    • Srinivas, K.V.N.S. & Das, B. Iodine catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones: A simple and efficient procedure for the Biginelli reaction. Synthesis 2091-2093 (2004).
    • Srinivas, K.V.N.S. & Das, B. Iodine catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thiones: A simple and efficient procedure for the Biginelli reaction. Synthesis 2091-2093 (2004).
  • 22
    • 15744393262 scopus 로고    scopus 로고
    • New protocol for Biginelli reactiona practical synthesis of monastrol
    • Bose, D.S., Sudharshan, M. & Chavhan, S.W. New protocol for Biginelli reactiona practical synthesis of monastrol. ARKIVOC iii, 228-236 (2005).
    • (2005) ARKIVOC , vol.3 , pp. 228-236
    • Bose, D.S.1    Sudharshan, M.2    Chavhan, S.W.3
  • 23
    • 0037474675 scopus 로고    scopus 로고
    • Silica sulfuric acid: An efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones
    • Salehi, P., Dabiri, M., Zolfigol, M.A. & Fard, M.A.B. Silica sulfuric acid: An efficient and reusable catalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. Tetrahedron Lett. 44, 2889-2891 (2003).
    • (2003) Tetrahedron Lett , vol.44 , pp. 2889-2891
    • Salehi, P.1    Dabiri, M.2    Zolfigol, M.A.3    Fard, M.A.B.4
  • 24
    • 33746014047 scopus 로고    scopus 로고
    • Bose, D.S., Chary, M.V. & Mereyala, H.B. Water-tolerant and reusable catalyst for the one-pot synthesis of dihydropyrimidine-2-(1H -ones under solvent-free conditions. Heterocyles 68, 1217-1224 (2006).
    • Bose, D.S., Chary, M.V. & Mereyala, H.B. Water-tolerant and reusable catalyst for the one-pot synthesis of dihydropyrimidine-2-(1H -ones under solvent-free conditions. Heterocyles 68, 1217-1224 (2006).
  • 25
    • 33644989059 scopus 로고    scopus 로고
    • A practical and green approach towards synthesis of dihydropyrimidinones: Using heteropoly acids as efficient catalysts
    • Rafiee, E. & Jafari, H. A practical and green approach towards synthesis of dihydropyrimidinones: Using heteropoly acids as efficient catalysts. Bioorg. Med. Chem. Lett. 16, 2463-2466 (2006).
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 2463-2466
    • Rafiee, E.1    Jafari, H.2
  • 26
    • 0036752261 scopus 로고    scopus 로고
    • Evidence that monastrol is an allosteric inhibitor of the mitotic kinesin Eg5
    • Maliga, Z., Kapoor, T.M. & Mitchinson, T.J. Evidence that monastrol is an allosteric inhibitor of the mitotic kinesin Eg5. Chem. Biol. 9, 989-996 (2000).
    • (2000) Chem. Biol , vol.9 , pp. 989-996
    • Maliga, Z.1    Kapoor, T.M.2    Mitchinson, T.J.3
  • 27
    • 1842763689 scopus 로고    scopus 로고
    • Combining synthetic and analytical strategies for preparative HPLC enantioseparation of monastrol racemic mixture
    • Cavazzini, A. et al. Combining synthetic and analytical strategies for preparative HPLC enantioseparation of monastrol racemic mixture. Biotechnol. Prog. 20, 603-612 (2004).
    • (2004) Biotechnol. Prog , vol.20 , pp. 603-612
    • Cavazzini, A.1
  • 28
    • 28444438118 scopus 로고    scopus 로고
    • Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: Asymmetric synthesis of dihydropyrimidines
    • Huang, Y., Yang, F. & Zhu, C. Highly enantioselective Biginelli reaction using a new chiral ytterbium catalyst: Asymmetric synthesis of dihydropyrimidines. J. Am. Chem. Soc. 127, 16386-16387 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 16386-16387
    • Huang, Y.1    Yang, F.2    Zhu, C.3
  • 29
    • 1642360667 scopus 로고    scopus 로고
    • Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones
    • Lengar, A. & Kappe, C.O. Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones. Org. Lett. 6, 771-774 (2004).
    • (2004) Org. Lett , vol.6 , pp. 771-774
    • Lengar, A.1    Kappe, C.O.2
  • 30
    • 22844439029 scopus 로고    scopus 로고
    • Microwave-enhanced and metal-catalyzed functionalizations of the 4-aryl-dihydropyrimidone template
    • Wannberg, J., Dallinger, D., Kappe, C.O. & Larhed, M. Microwave-enhanced and metal-catalyzed functionalizations of the 4-aryl-dihydropyrimidone template. J. Comb. Chem. 7, 574-583 (2005).
    • (2005) J. Comb. Chem , vol.7 , pp. 574-583
    • Wannberg, J.1    Dallinger, D.2    Kappe, C.O.3    Larhed, M.4
  • 31
    • 0346847647 scopus 로고    scopus 로고
    • Building dihydropyrimidine libraries via microwave-assisted Biginelli multicomponent reactions
    • Kappe, C.O. & Stadler, A. Building dihydropyrimidine libraries via microwave-assisted Biginelli multicomponent reactions. Methods Enzymol. 369, 197-223 (2003).
    • (2003) Methods Enzymol , vol.369 , pp. 197-223
    • Kappe, C.O.1    Stadler, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.