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Volumn 75, Issue 2, 2010, Pages 228-232

High throughput receptor-based virtual screening under ZINC database, synthesis, and biological evaluation of ketol-acid reductoisomerase inhibitors

Author keywords

Docking; High throughput virtual screening; KARI; KARI activity

Indexed keywords

ENZYME INHIBITOR; KETOL ACID REDUCTOISOMERASE; KETOL ACID REDUCTOISOMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 74549178564     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00924.x     Document Type: Article
Times cited : (21)

References (38)
  • 2
    • 37049182338 scopus 로고
    • Acetolactate synthase is the site of action of two sulfonylurea herbicides in higher plants
    • Chaleff R.S., Mauvais C.J. (1984) Acetolactate synthase is the site of action of two sulfonylurea herbicides in higher plants. Science 224 : 1443 1445.
    • (1984) Science , vol.224 , pp. 1443-1445
    • Chaleff, R.S.1    Mauvais, C.J.2
  • 3
    • 84957869700 scopus 로고
    • Imidazolinones. Potent inhibitors of acetohydroxy acid synthase
    • Shaner D.L., Anderson P.C., Stidham M.A. (1984) Imidazolinones. Potent inhibitors of acetohydroxy acid synthase. Plant Physiol 76 : 545 546.
    • (1984) Plant Physiol , vol.76 , pp. 545-546
    • Shaner, D.L.1    Anderson, P.C.2    Stidham, M.A.3
  • 4
    • 0020902852 scopus 로고
    • Analytical investigation of the process for manufacturing 1,2,4-1H-triazole
    • Hung S. (1983) Analytical investigation of the process for manufacturing 1,2,4-1H-triazole. Ind Chem 11 : 291 299.
    • (1983) Ind Chem , vol.11 , pp. 291-299
    • Hung, S.1
  • 6
    • 0034868638 scopus 로고    scopus 로고
    • Enzymology, structure, and dynamics of acetohydroxy acid isomeroreductase
    • Dumas R., Biou V.F., Douce H.R., Duggleby R.G. (2001) Enzymology, structure, and dynamics of acetohydroxy acid isomeroreductase. Acc Chem Res 34 : 399 408.
    • (2001) Acc Chem Res , vol.34 , pp. 399-408
    • Dumas, R.1    Biou, V.F.2    Douce, H.R.3    Duggleby, R.G.4
  • 7
    • 0028045123 scopus 로고
    • Herbicidal activity of an isopropylmalate dehydrogenase inhibitor
    • Wittenbach V.A., Teaney P.W., Rayner D.R., Schloss J.V. (1993) Herbicidal activity of an isopropylmalate dehydrogenase inhibitor. Plant Physiol 106 : 321 328.
    • (1993) Plant Physiol , vol.106 , pp. 321-328
    • Wittenbach, V.A.1    Teaney, P.W.2    Rayner, D.R.3    Schloss, J.V.4
  • 8
    • 0029010594 scopus 로고
    • Evidence for two catalytically different magnesium-binding sites in acetohydroxy acid isomeroreductase by site-directed mutagenesis
    • Dumas R., Butikofer M.C., Job D., Douce R. (1995) Evidence for two catalytically different magnesium-binding sites in acetohydroxy acid isomeroreductase by site-directed mutagenesis. Biochemistry 34 : 6026 6036.
    • (1995) Biochemistry , vol.34 , pp. 6026-6036
    • Dumas, R.1    Butikofer, M.C.2    Job, D.3    Douce, R.4
  • 9
    • 0024977333 scopus 로고
    • Mechanism of ketol acid reductoisomerase. Steady-state analysis and metal ion requirement
    • Chunduru S.K., Mrachko G.T., Calvo K.C. (1989) Mechanism of ketol acid reductoisomerase. Steady-state analysis and metal ion requirement. Biochemistry 28 : 486 493.
    • (1989) Biochemistry , vol.28 , pp. 486-493
    • Chunduru, S.K.1    Mrachko, G.T.2    Calvo, K.C.3
  • 10
    • 0024283582 scopus 로고
    • The herbicidally active experimental compound Hoe 704 is a potent inhibitor of the enzyme acetolactate reductoisomerase
    • Schulz A., Sponemann P., Kocher H., Wengenmayer F. (1988) The herbicidally active experimental compound Hoe 704 is a potent inhibitor of the enzyme acetolactate reductoisomerase. FEBS Lett 238 : 375 378.
    • (1988) FEBS Lett , vol.238 , pp. 375-378
    • Schulz, A.1    Sponemann, P.2    Kocher, H.3    Wengenmayer, F.4
  • 11
    • 0025366343 scopus 로고
    • Oxalyl hydroxamates as reaction-intermediate analogs for ketol-acid reductoisomerase
    • Aulabaugh A., Schloss J.V. (1990) Oxalyl hydroxamates as reaction-intermediate analogs for ketol-acid reductoisomerase. Biochemistry 29 : 2824 2840.
    • (1990) Biochemistry , vol.29 , pp. 2824-2840
    • Aulabaugh, A.1    Schloss, J.V.2
  • 13
    • 13944269884 scopus 로고    scopus 로고
    • Cyclopropane-1,1-dicarboxylate is a slow-, tight-binding inhibitor of rice ketol-acid reductoisomerase
    • Lee Y.T., Ta H.T., Duggleby R.G. (2005) Cyclopropane-1,1-dicarboxylate is a slow-, tight-binding inhibitor of rice ketol-acid reductoisomerase. Plant Sci 168 : 1035 1040.
    • (2005) Plant Sci , vol.168 , pp. 1035-1040
    • Lee, Y.T.1    Ta, H.T.2    Duggleby, R.G.3
  • 14
    • 34250219961 scopus 로고    scopus 로고
    • Synthesis bioactivity theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor
    • Liu X.H., Chen P.Q., Wang B.L., Li Y.H., Wang S.H., Li Z.M. (2007) Synthesis bioactivity theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor. Bioorg Med Chem Lett 17 : 3784 3788.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 3784-3788
    • Liu, X.H.1    Chen, P.Q.2    Wang, B.L.3    Li, Y.H.4    Wang, S.H.5    Li, Z.M.6
  • 15
    • 36248964113 scopus 로고    scopus 로고
    • Structure bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo- propanecarboxamide
    • Liu X.H., Chen P.Q., He F.Q., Li Y.H., Wang S.H., Li Z.M. (2007) Structure bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo- propanecarboxamide. Struct Chem 5 : 563 568.
    • (2007) Struct Chem , vol.5 , pp. 563-568
    • Liu, X.H.1    Chen, P.Q.2    He, F.Q.3    Li, Y.H.4    Wang, S.H.5    Li, Z.M.6
  • 16
    • 65649102383 scopus 로고    scopus 로고
    • Synthesis bioactivity and SAR study of N′-(5-substituted-1,3,4- thiadiazol-2-yl)-N-cyclopropyformyl -thiourea as ketol-acid reductoisomerase inhibitor
    • Liu X.H., Zhang C.Y., Guo W.C., Li Y.H., Chen P.Q., Wang T., Dong W.L., Sun H.W., Li Z.M. (2009) Synthesis bioactivity and SAR study of N′-(5-substituted-1,3,4-thiadiazol-2-yl)-N-cyclopropyformyl -thiourea as ketol-acid reductoisomerase inhibitor. J Enzyme Inhib Med Chem 24 : 545 552.
    • (2009) J Enzyme Inhib Med Chem , vol.24 , pp. 545-552
    • Liu, X.H.1    Zhang, C.Y.2    Guo, W.C.3    Li, Y.H.4    Chen, P.Q.5    Wang, T.6    Dong, W.L.7    Sun, H.W.8    Li, Z.M.9
  • 17
    • 0031718499 scopus 로고    scopus 로고
    • Inhibitors of branched-chain amino acid biosynthesis as potential antituberculosis agents
    • Grandoni J.A., Marta P.T., Schloss J.V. (1998) Inhibitors of branched-chain amino acid biosynthesis as potential antituberculosis agents. J Antimicrob Chemother 42 : 475 482.
    • (1998) J Antimicrob Chemother , vol.42 , pp. 475-482
    • Grandoni, J.A.1    Marta, P.T.2    Schloss, J.V.3
  • 19
    • 65649116303 scopus 로고    scopus 로고
    • Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl) cyclopropanecarboxamides
    • Liu X.H., Shi Y.X., Ma Y., Zhang C.Y., Dong W.L., Li P., Wang B.L., Li B.J., Li Z.M. (2009) Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl) cyclopropanecarboxamides. Eur J Med Chem 44 : 2782 2786.
    • (2009) Eur J Med Chem , vol.44 , pp. 2782-2786
    • Liu, X.H.1    Shi, Y.X.2    Ma, Y.3    Zhang, C.Y.4    Dong, W.L.5    Li, P.6    Wang, B.L.7    Li, B.J.8    Li, Z.M.9
  • 20
    • 4444287264 scopus 로고    scopus 로고
    • 3D-Database searching based on the crystal structure of ketol-acid reductoisomerase (KARI) complex
    • Wang B.L., Li Z.M., Ma Y., Wang J.G., Luo X.M. (2004) 3D-Database searching based on the crystal structure of ketol-acid reductoisomerase (KARI) complex. Chin J Org Chem 24 : 973 976.
    • (2004) Chin J Org Chem , vol.24 , pp. 973-976
    • Wang, B.L.1    Li, Z.M.2    Ma, Y.3    Wang, J.G.4    Luo, X.M.5
  • 21
    • 74549188160 scopus 로고
    • Synthesis of para-substituted benzyl cyclopropyl ketones
    • Razus A.C., Bartha E., Arvay Z., Glatz A.M. (1984) Synthesis of para-substituted benzyl cyclopropyl ketones. Rev Roum Chim 29 : 719 725.
    • (1984) Rev Roum Chim , vol.29 , pp. 719-725
    • Razus, A.C.1    Bartha, E.2    Arvay, Z.3    Glatz, A.M.4
  • 22
    • 0001936433 scopus 로고
    • Physical properties and chemical constitution. I. Esters of normal dibasic acids and substituted malonic acids
    • Vogel A.I. (1934) Physical properties and chemical constitution. I. Esters of normal dibasic acids and substituted malonic acids. J Chem Soc 333 341.
    • (1934) J Chem Soc , pp. 333-341
    • Vogel, A.I.1
  • 23
    • 0041781917 scopus 로고    scopus 로고
    • Reaction of cyclopropane carboxylic acid derivatives with sulphur tetrafluoride-an example of a diastereoselective ring opening
    • Hell Z., Finta Z., Dmowski W., Faigl F., Pustovit Y.M., Toke L., Harmat V. (2000) reaction of cyclopropane carboxylic acid derivatives with sulphur tetrafluoride-an example of a diastereoselective ring opening. J Fluor Chem 104 : 297 301.
    • (2000) J Fluor Chem , vol.104 , pp. 297-301
    • Hell, Z.1    Finta, Z.2    Dmowski, W.3    Faigl, F.4    Pustovit, Y.M.5    Toke, L.6    Harmat, V.7
  • 24
    • 84981834366 scopus 로고
    • Preparation of -amino acid esters by alcoholysis of the methyl esters
    • Brenner M., Huber W. (1953) Preparation of -amino acid esters by alcoholysis of the methyl esters. Helv Chim Acta 36 : 1109 1115.
    • (1953) Helv Chim Acta , vol.36 , pp. 1109-1115
    • Brenner, M.1    Huber, W.2
  • 25
    • 74549194238 scopus 로고
    • Action of sulfuric acid on certain derivatives of cyclopropane
    • Allen C.F.H., Boyer R. (1933) Action of sulfuric acid on certain derivatives of cyclopropane. Can J Res 9 : 159 168.
    • (1933) Can J Res , vol.9 , pp. 159-168
    • Allen, C.F.H.1    Boyer, R.2
  • 26
    • 33947455187 scopus 로고
    • Small-ring compounds. V. Synthesis of cyclo-propanecarboxaldehyde by the MacFadyen-Stevens reduction
    • Roberts J.D. (1951) Small-ring compounds. V. Synthesis of cyclo-propanecarboxaldehyde by the MacFadyen-Stevens reduction. J Am Chem Soc 73 : 2959.
    • (1951) J Am Chem Soc , vol.73 , pp. 2959
    • Roberts, J.D.1
  • 27
    • 37049048301 scopus 로고
    • Reaction of N-carboxy-amino acid anhydrides with hydrochlorides of hydroxylamine, O-alkylhydroxylamines, and amines; Syntheses of aminohydroxamic acids, amidooxy peptides, and -amino acid amides
    • Knobler Y., Bittner S., Frankel M. (1964) Reaction of N-carboxy-amino acid anhydrides with hydrochlorides of hydroxylamine, O-alkylhydroxylamines, and amines; syntheses of aminohydroxamic acids, amidooxy peptides, and -amino acid amides. J Chem Soc 3941 3951.
    • (1964) J Chem Soc , pp. 3941-3951
    • Knobler, Y.1    Bittner, S.2    Frankel, M.3
  • 28
    • 0034774903 scopus 로고    scopus 로고
    • Some furfural derivatives as nitrification inhibitors
    • Datta A., Walia S., Parma B.S. (2001) Some furfural derivatives as nitrification inhibitors. J Agric Food Chem 49 : 4726 4731.
    • (2001) J Agric Food Chem , vol.49 , pp. 4726-4731
    • Datta, A.1    Walia, S.2    Parma, B.S.3
  • 29
    • 74549182372 scopus 로고
    • Synthesis of 3-aminothenoyl- and 3-aminofuroylrhodanines
    • Sy M., de Malleray B. (1963) Synthesis of 3-aminothenoyl- and 3-aminofuroylrhodanines. Bull Soc Chim Fr 3 : 1278 1279.
    • (1963) Bull Soc Chim Fr , vol.3 , pp. 1278-1279
    • Sy, M.1    De Malleray, B.2
  • 30
    • 0001066347 scopus 로고
    • Furan compounds. V. Preparation and configuration of furyl ketoximes
    • Ocskay G., Vargha L. (1958) Furan compounds. V. Preparation and configuration of furyl ketoximes. Tetrahedron 2 : 140 150.
    • (1958) Tetrahedron , vol.2 , pp. 140-150
    • Ocskay, G.1    Vargha, L.2
  • 31
    • 74549192555 scopus 로고
    • Synthesis of aminothiadiazoles and the corresponding sulfonamide derivatives
    • Wojahn H., Wuckel H. (1951) Synthesis of aminothiadiazoles and the corresponding sulfonamide derivatives. Arch Pharm 284 : 53 62.
    • (1951) Arch Pharm , vol.284 , pp. 53-62
    • Wojahn, H.1    Wuckel, H.2
  • 32
    • 74549191226 scopus 로고
    • Heterocyclic carboxylic acids., GB
    • 816531.
    • Henkel C. (1959) Heterocyclic carboxylic acids., GB 816531. Chem Abstr 54 : 7325.
    • (1959) Chem Abstr , vol.54 , pp. 7325
    • Henkel, C.1
  • 33
    • 0025534452 scopus 로고
    • Design, synthesis and biological screening of new s-triazolothiadiazine derivatives
    • Chande M.S., Karnik B.M., Inamdar A.N., Ganguly N. (1990) Design, synthesis and biological screening of new s-triazolothiadiazine derivatives. J Indian Chem Soc 67 : 220 222.
    • (1990) J Indian Chem Soc , vol.67 , pp. 220-222
    • Chande, M.S.1    Karnik, B.M.2    Inamdar, A.N.3    Ganguly, N.4
  • 34
    • 0018165402 scopus 로고
    • Reaction of cyanates with carboxylic acid hydrazides
    • Zinner G., Neitzel M., Holdt I. (1978) Reaction of cyanates with carboxylic acid hydrazides. Arch Pharm (Weinheim) 311 : 1050 1055.
    • (1978) Arch Pharm (Weinheim) , vol.311 , pp. 1050-1055
    • Zinner, G.1    Neitzel, M.2    Holdt, I.3
  • 35
    • 74549166378 scopus 로고
    • Antibacterial cephalosporins. de
    • 2145928.
    • Crast L., Leonard B. Jr., (1972) Antibacterial cephalosporins. DE 2145928. Chem Abstr 77 : 48487.
    • (1972) Chem Abstr , vol.77 , pp. 48487
    • Crast, L.1    Leonard Jr., B.2
  • 36
    • 0000248113 scopus 로고
    • Rapid diagnosis of ALS/AHAS-resistant weeds
    • Gerwick B.C., Mireles L.C., Eilers R.J. (1993) Rapid diagnosis of ALS/AHAS-resistant weeds. Weed Technol 7 : 519 524.
    • (1993) Weed Technol , vol.7 , pp. 519-524
    • Gerwick, B.C.1    Mireles, L.C.2    Eilers, R.J.3
  • 38
    • 0014949207 scopus 로고
    • Cleavage of structural proteins during the assembly of the head of bacteriophage T4
    • Laemmli U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227 : 680 685.
    • (1970) Nature , vol.227 , pp. 680-685
    • Laemmli, U.K.1


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