메뉴 건너뛰기




Volumn 53, Issue 6, 2010, Pages 2401-2408

Identification of 3,4-dihydroisoquinoline-2(1H)-sulfonamides as potent carbonic anhydrase inhibitors: Synthesis, biological evaluation, and enzyme-ligand X-ray studies

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 1 CYCLOHEXYL 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 1 CYCLOPENTYL 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 1 CYCLOPROPYL 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 6,7 DIMETHOXY 1 ETHYL 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 6,7 DIMETHOXY 1 ISOPROPYL 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 6,7 DIMETHOXY 1 METHYL 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 6,7 DIMETHOXY 1 PROPYL 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; 6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLINE 2(1H) SULFONAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XIV; SULFONAMIDE; UNCLASSIFIED DRUG;

EID: 77949869987     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9014026     Document Type: Article
Times cited : (53)

References (58)
  • 2
    • 46849121802 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity
    • Supuran, C. T.; Di Fiore, A.; De Simone, G. Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin. Emerging Drugs 2008, 13, 383-392.
    • (2008) Expert Opin. Emerging Drugs , vol.13 , pp. 383-392
    • Supuran, C.T.1    Di Fiore, A.2    De Simone, G.3
  • 3
    • 34249670767 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors and the management of cancer
    • Pastorekova, S.; Kopacek, J.; Pastorek, J. Carbonic anhydrase inhibitors and the management of cancer. Curr. Top. Med. Chem. 2007, 7, 865-878.
    • (2007) Curr. Top. Med. Chem. , vol.7 , pp. 865-878
    • Pastorekova, S.1    Kopacek, J.2    Pastorek, J.3
  • 5
    • 38849143765 scopus 로고    scopus 로고
    • Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators
    • Supuran, C. T. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Discovery 2008, 7, 168-181.
    • (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 168-181
    • Supuran, C.T.1
  • 6
    • 66149131065 scopus 로고    scopus 로고
    • Therapeutic applications of glycosidic carbonic anhydrase inhibitors
    • Winum, J. Y.; Poulsen, S. A.; Supuran, C. T. Therapeutic applications of glycosidic carbonic anhydrase inhibitors. Med. Res. Rev. 2009, 29, 419-435.
    • (2009) Med. Res. Rev. , vol.29 , pp. 419-435
    • Winum, J.Y.1    Poulsen, S.A.2    Supuran, C.T.3
  • 7
    • 37549037851 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Interaction of 2-(hydrazinocarbonyl)-3- phenyl-lH-indole-5-sulfonamide with 12 mammalian isoforms: Kinetic and X-ray crystallographic studies
    • Guzel, O.; Temperini, C.; Innocenti, A.; Scozzafava, A.; Salman, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Interaction of 2-(hydrazinocarbonyl)-3-phenyl-lH-indole-5-sulfonamide with 12 mammalian isoforms: kinetic and X-ray crystallographic studies. Bioorg. Med. Chem. Lett. 2008, 18, 152-158.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 152-158
    • Guzel, O.1    Temperini, C.2    Innocenti, A.3    Scozzafava, A.4    Salman, A.5    Supuran, C.T.6
  • 8
    • 44949190364 scopus 로고    scopus 로고
    • Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs
    • Thiry, A.; Supuran, C. T.; Masereel, B.; Dogne, J. M. Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. J. Med. Chem. 2008, 51, 3051-3056.
    • (2008) J. Med. Chem. , vol.51 , pp. 3051-3056
    • Thiry, A.1    Supuran, C.T.2    Masereel, B.3    Dogne, J.M.4
  • 13
    • 0041919643 scopus 로고    scopus 로고
    • Protease inhibitors of the sulfonamide type: Anticancer, antiinflammatory, and antiviral agents
    • Supuran, C. T.; Casini, A.; Scozzafava, A. Protease inhibitors of the sulfonamide type: anticancer, antiinflammatory, and antiviral agents. Med. Res. Rev. 2003, 23, 535-558.
    • (2003) Med. Res. Rev. , vol.23 , pp. 535-558
    • Supuran, C.T.1    Casini, A.2    Scozzafava, A.3
  • 14
    • 33746934196 scopus 로고    scopus 로고
    • New zinc binding motifs in the design of selective carbonic anhydrase inhibitors
    • Winum, J. Y.; Scozzafava, A.; Montero, J. L.; Supuran, C. T. New zinc binding motifs in the design of selective carbonic anhydrase inhibitors. Mini-Rev. Med. Chem. 2006, 5, 921-936.
    • (2006) Mini-Rev. Med. Chem. , vol.5 , pp. 921-936
    • Winum, J.Y.1    Scozzafava, A.2    Montero, J.L.3    Supuran, C.T.4
  • 15
    • 42149114451 scopus 로고    scopus 로고
    • Diuretics: From classical carbonic anhydrase inhibitors to novel applications of the sulfonamides
    • Supuran, C. T. Diuretics: from classical carbonic anhydrase inhibitors to novel applications of the sulfonamides. Curr. Pharm. Des. 2008, 14, 641-648.
    • (2008) Curr. Pharm. Des. , vol.14 , pp. 641-648
    • Supuran, C.T.1
  • 16
    • 68549101744 scopus 로고    scopus 로고
    • Carbonic anhydrase-encoded dynamic constitutional libraries: Toward the discovery of isozyme-specific inhibitors
    • Nasr, G.; Petit, E.; Vullo, D.; Winum, J. Y.; Supuran, C. T.; Barboiu, M. Carbonic anhydrase-encoded dynamic constitutional libraries: toward the discovery of isozyme-specific inhibitors. J. Med. Chem. 2009, 52, 853-859.
    • (2009) J. Med. Chem. , vol.52 , pp. 853-859
    • Nasr, G.1    Petit, E.2    Vullo, D.3    Winum, J.Y.4    Supuran, C.T.5    Barboiu, M.6
  • 18
  • 19
    • 60549085611 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Comparison of chlorthalidone and indapamide X-ray crystal structures in adducts with isozyme II: When three water molecules and the keto-enol tautomerism make the difference
    • Temperini, C.; Cecchi, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Comparison of chlorthalidone and indapamide X-ray crystal structures in adducts with isozyme II: when three water molecules and the keto-enol tautomerism make the difference. J. Med. Chem. 2009, 52, 322-328.
    • (2009) J. Med. Chem. , vol.52 , pp. 322-328
    • Temperini, C.1    Cecchi, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 20
    • 1842639484 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide
    • Abbate, F.; Casini, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide. Bioorg. Med. Chem. Lett. 2004, 14, 2357-2361.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2357-2361
    • Abbate, F.1    Casini, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 21
    • 0344193512 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV
    • Casini, A.; Antel, J.; Abbate, F.; Scozzafava, A.; David, S.; Waldeck, H.; Schafer, S.; Supuran, C. T. Carbonic anhydrase inhibitors: SAR and X-ray crystallographic study for the interaction of sugar sulfamates/sulfamides with isozymes I, II and IV. Bioorg. Med. Chem. Lett. 2003, 13, 841-845.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 841-845
    • Casini, A.1    Antel, J.2    Abbate, F.3    Scozzafava, A.4    David, S.5    Waldeck, H.6    Schafer, S.7    Supuran, C.T.8
  • 23
    • 41949096461 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct
    • Temperini, C.; Cecchi, A.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Bioorg. Med. Chem. Lett. 2008, 18, 2567-2573.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2567-2573
    • Temperini, C.1    Cecchi, A.2    Scozzafava, A.3    Supuran, C.T.4
  • 24
    • 33845353402 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue
    • Winum, J. Y.; Temperini, C.; El Cheikh, K.; Innocenti, A.; Vullo, D.; Ciattini, S.; Montero, J. L.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue. J. Med. Chem. 2006, 49, 7024-7031.
    • (2006) J. Med. Chem. , vol.49 , pp. 7024-7031
    • Winum, J.Y.1    Temperini, C.2    El Cheikh, K.3    Innocenti, A.4    Vullo, D.5    Ciattini, S.6    Montero, J.L.7    Scozzafava, A.8    Supuran, C.T.9
  • 25
    • 33745644458 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX
    • Alterio, V.; Vitale, R. M.; Monti, S. M.; Pedone, C.; Scozzafava, A.; Cecchi, A.; De Simone, G.; Supuran, C. T. Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX. J. Am. Chem. Soc. 2006, 128, 8329-8335.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 8329-8335
    • Alterio, V.1    Vitale, R.M.2    Monti, S.M.3    Pedone, C.4    Scozzafava, A.5    Cecchi, A.6    De Simone, G.7    Supuran, C.T.8
  • 26
    • 24744467784 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors: Stacking with Phel31 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II
    • Menchise, V.; De Simone, G.; Alterio, V.; Di Fiore, A.; Pedone, C.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: stacking with Phel31 determines active site binding region of inhibitors as exemplified by the X-ray crystal structure of a membrane-impermeant antitumor sulfonamide complexed with isozyme II. J. Med. Chem. 2005, 48, 5721-5727.
    • (2005) J. Med. Chem. , vol.48 , pp. 5721-5727
    • Menchise, V.1    De Simone, G.2    Alterio, V.3    Di Fiore, A.4    Pedone, C.5    Scozzafava, A.6    Supuran, C.T.7
  • 30
    • 0024218271 scopus 로고
    • Refined structure of human carbonic anhydrase II at 2.0 Å resolution
    • Eriksson, A. E.; Jones, T. A.; Liljas, A. Refined structure of human carbonic anhydrase II at 2.0 Å resolution. Proteins 1988, 4, 274-282.
    • (1988) Proteins , vol.4 , pp. 274-282
    • Eriksson, A.E.1    Jones, T.A.2    Liljas, A.3
  • 31
    • 33644956925 scopus 로고    scopus 로고
    • Ultrahigh resolution crystal structures of human carbonic anhydrases i and II complexed with two-prong inhibitors reveal the molecular basis of high affinity
    • Jude, K. M.; Banerjee, A. L.; Haldar, M. K.; Manokaran, S.; Roy, B.; Mallik, S.; Srivastava, D. K.; Christianson, D. W. Ultrahigh resolution crystal structures of human carbonic anhydrases I and II complexed with "two-prong" inhibitors reveal the molecular basis of high affinity. J. Am. Chem. Soc. 2006, 128, 3011-3018.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 3011-3018
    • Jude, K.M.1    Banerjee, A.L.2    Haldar, M.K.3    Manokaran, S.4    Roy, B.5    Mallik, S.6    Srivastava, D.K.7    Christianson, D.W.8
  • 32
    • 0032897494 scopus 로고    scopus 로고
    • An analysis of conformational changes on protein-protein association: Implications for predictive docking
    • Betts, M. J.; Sternberg, M. J. An analysis of conformational changes on protein-protein association: implications for predictive docking. Protein Eng. 1999, 12, 271-283.
    • (1999) Protein Eng. , vol.12 , pp. 271-283
    • Betts, M.J.1    Sternberg, M.J.2
  • 33
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. MoI. Biol. 1997, 267,727-748.
    • (1997) J. MoI. Biol. , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 34
    • 0028935889 scopus 로고
    • Structural basis of inhibitor affinity to variants of human carbonic anhydrase II
    • Nair, S. K.; Krebs, J. F.; Christianson, D. W.; Fierke, C. A. Structural basis of inhibitor affinity to variants of human carbonic anhydrase II. Biochemistry 1995, 34,3981-3989.
    • (1995) Biochemistry , vol.34 , pp. 3981-3989
    • Nair, S.K.1    Krebs, J.F.2    Christianson, D.W.3    Fierke, C.A.4
  • 36
    • 1342304082 scopus 로고    scopus 로고
    • Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: Implications for selective inhibition of membrane-associated isozymes
    • Whittington, D. A.; Grubb, J. H.; Waheed, A.; Shah, G. N.; Sly, W. S.; Christianson, D. W. Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: implications for selective inhibition of membrane-associated isozymes. J. Biol. Chem. 2004, 279, 7223-7228.
    • (2004) J. Biol. Chem. , vol.279 , pp. 7223-7228
    • Whittington, D.A.1    Grubb, J.H.2    Waheed, A.3    Shah, G.N.4    Sly, W.S.5    Christianson, D.W.6
  • 37
    • 2142653958 scopus 로고
    • Tetrahydroisoquinolines. I. l-Alkyl-6, 7-dihydroxy-l,2,3,4- tetrahydroisoquinolines
    • Craig, P. N.; Nabenhauer, F. P.; Williams, P. M.; Macko, E.; Toner, J. Tetrahydroisoquinolines. I. l-Alkyl-6, 7-dihydroxy-l,2,3,4- tetrahydroisoquinolines. J. Am. Chem. Soc. 1952, 74, 1316-1317.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 1316-1317
    • Craig, P.N.1    Nabenhauer, F.P.2    Williams, P.M.3    Macko, E.4    Toner, J.5
  • 38
    • 77949854801 scopus 로고
    • Compounds related to emetine. I. Synthesis of l-(l,2,3,4-tetrahydro-6,7- dimethoxy-l-propyl-2-isoquinolyl)-4-(l,2,3,4-tetrahydro-6,7-dimethoxy-l- isoquinolyl)butane acid oxalate
    • Barbier, A. M.; Rumpf, P. Compounds related to emetine. I. Synthesis of l-(l,2,3,4-tetrahydro-6,7-dimethoxy-l-propyl-2-isoquinolyl)-4-(l,2,3, 4-tetrahydro-6,7-dimethoxy-l-isoquinolyl)butane acid oxalate. Bull. Soc. Chim. Fr. 1953, 293-296.
    • (1953) Bull. Soc. Chim. Fr. , pp. 293-296
    • Barbier, A.M.1    Rumpf, P.2
  • 39
    • 84985204853 scopus 로고
    • Study of the oxidation of 6,7- And 7,8-dimethoxytetrahydroisoquinolin-4- ols and the reactivity of the carbonyl group of 6,7- dimethoxytetrahydroisoquinol-4-one
    • Leseche, B.; Gilbert, J.; Viel, C. Study of the oxidation of 6,7- and 7,8-dimethoxytetrahydroisoquinolin-4-ols and the reactivity of the carbonyl group of 6,7-dimethoxytetrahydroisoquinol-4-one. J. Heterocycl. Chem. 1981, 18, 143-153.
    • (1981) J. Heterocycl. Chem. , vol.18 , pp. 143-153
    • Leseche, B.1    Gilbert, J.2    Viel, C.3
  • 40
    • 5644266177 scopus 로고    scopus 로고
    • One-step preparation of 1-substituted tetrahydroisoquinolines via the Pictet-Spengler reaction using zeolite catalysts
    • Hegedues, A.; Hell, Z. One-step preparation of 1-substituted tetrahydroisoquinolines via the Pictet-Spengler reaction using zeolite catalysts. Tetrahedron Lett. 2004, 45, 8553-8555.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 8553-8555
    • Hegedues, A.1    Hell, Z.2
  • 41
    • 0015239422 scopus 로고
    • The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C
    • Khalifah, R. G. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem. 1971, 246, 2561-2573.
    • (1971) J. Biol. Chem. , vol.246 , pp. 2561-2573
    • Khalifah, R.G.1
  • 42
    • 28144452672 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. the mitochondrialisozyme VB as a new target for sulfonamide and sulfamate inhibitors
    • Nishimori, I.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Carbonic anhydrase inhibitors. The mitochondrialisozyme VB as a new target for sulfonamide and sulfamate inhibitors. J. Med. Chem. 2005, 48, 7860-7866.
    • (2005) J. Med. Chem. , vol.48 , pp. 7860-7866
    • Nishimori, I.1    Vullo, D.2    Innocenti, A.3    Scozzafava, A.4    Mastrolorenzo, A.5    Supuran, C.T.6
  • 44
    • 33846458646 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors
    • Nishimori, I.; Minakuchi, T.; Onishi, S.; Vullo, D.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. J. Med. Chem. 2007, 50, 381-388.
    • (2007) J. Med. Chem. , vol.50 , pp. 381-388
    • Nishimori, I.1    Minakuchi, T.2    Onishi, S.3    Vullo, D.4    Scozzafava, A.5    Supuran, C.T.6
  • 45
    • 33645402549 scopus 로고    scopus 로고
    • Carbonic anhydrase inhibitors DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs
    • Nishimori, I.; Minakuchi, T.; Morimoto, K.; Sano, S.; Onishi, S.; Takeuchi, H.; Vullo, D.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. J. Med. Chem. 2006, 49, 2117-2126.
    • (2006) J. Med. Chem. , vol.49 , pp. 2117-2126
    • Nishimori, I.1    Minakuchi, T.2    Morimoto, K.3    Sano, S.4    Onishi, S.5    Takeuchi, H.6    Vullo, D.7    Scozzafava, A.8    Supuran, C.T.9
  • 48
    • 0028103275 scopus 로고
    • The CCP4 suite: Programs for protein crystallography
    • The CCP4 suite: programs for protein crystallography. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1994, 50, 160-162.
    • (1994) Acta Crystallogr., Sect. D: Biol. Crystallogr. , vol.50 , pp. 160-162
  • 49
    • 0031283056 scopus 로고    scopus 로고
    • Histidine -carboxamide ligand substitutions in the zinc binding site of carbonic anhydrase II alter metal coordination geometry but retain catalytic activity
    • Lesburg, C. A.; Huang, C; Christianson, D. W.; Fierke, C. A. Histidine -carboxamide ligand substitutions in the zinc binding site of carbonic anhydrase II alter metal coordination geometry but retain catalytic activity. Biochemistry 1997, 36, 15780-15791.
    • (1997) Biochemistry , vol.36 , pp. 15780-15791
    • Lesburg, C.A.1    Huang, C.2    Christianson, D.W.3    Fierke, C.A.4
  • 56
    • 77949800944 scopus 로고    scopus 로고
    • version 8.0; Tripos Inc. 1699 South Hanley Road, St. Louis, MO 63144
    • SYBYL, version 8.0; Tripos Inc. (1699 South Hanley Road, St. Louis, MO 63144), 2005.
    • (2005) SYBYL
  • 58
    • 0026597444 scopus 로고
    • Free R value: A novel statistical quantity for assessing the accuracy of crystal structures
    • Brunger, A. T. Free R value: a novel statistical quantity for assessing the accuracy of crystal structures. Nature 1992, 355, 472-475.
    • (1992) Nature , vol.355 , pp. 472-475
    • Brunger, A.T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.