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Volumn 12, Issue 3, 2008, Pages 340-351

Molecular diversity in the context of leadlikeness: compound properties that enable effective biochemical screening

Author keywords

[No Author keywords available]

Indexed keywords

ADRENALIN; AMPHETAMINE; CARBOHYDRATE; DEXFENFLURAMINE; GALANTAMINE; MORPHINE; PEPTIDE; PHENTERMINE; PROTEIN; SEROTONIN;

EID: 49949151887     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2008.02.008     Document Type: Review
Times cited : (43)

References (49)
  • 1
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Basically set the stage for most of the druglikeness discussions that have followed since its publication.
    • Lipinski C.A., Lombardo F., Dominy B., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 23 (1997) 3-25. Basically set the stage for most of the druglikeness discussions that have followed since its publication.
    • (1997) Adv Drug Deliv Rev , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.3    Feeney, P.J.4
  • 2
    • 0037030653 scopus 로고    scopus 로고
    • Molecular properties that influence the oral bioavailability of drug candidates
    • Important recognition that free rotatable bonds are one key to oral bioavailability.
    • Veber D.F., Johnson S.R., Cheng H., Smith B.R., Ward K.W., and Kopple K.D. Molecular properties that influence the oral bioavailability of drug candidates. J Med Chem 45 (2002) 2615-2623. Important recognition that free rotatable bonds are one key to oral bioavailability.
    • (2002) J Med Chem , vol.45 , pp. 2615-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 3
    • 33646849102 scopus 로고    scopus 로고
    • Computational approaches to the prediction of blood-brain barrier permeability: a comparative analysis of central nervous system drugs versus secretase inhibitors for Alzheimer's disease
    • Rishton G.M., LaBonte K., Williams A.J., Kassam K., and Kolovanov E. Computational approaches to the prediction of blood-brain barrier permeability: a comparative analysis of central nervous system drugs versus secretase inhibitors for Alzheimer's disease. Curr Opin Drug Discov Drug Dev 9 (2006) 303-313
    • (2006) Curr Opin Drug Discov Drug Dev , vol.9 , pp. 303-313
    • Rishton, G.M.1    LaBonte, K.2    Williams, A.J.3    Kassam, K.4    Kolovanov, E.5
  • 4
    • 33845937770 scopus 로고    scopus 로고
    • Structure-brain exposure relationships
    • Hitchcock S.A., and Pennington L.D. Structure-brain exposure relationships. J Med Chem 26 (2006) 7559-7583
    • (2006) J Med Chem , vol.26 , pp. 7559-7583
    • Hitchcock, S.A.1    Pennington, L.D.2
  • 5
    • 0030756360 scopus 로고    scopus 로고
    • Reactive compounds and in vitro false positives in HTS
    • Identifies protein-reactive functional groups as covalent-acting false positives in biochemical assays and also characterizes the artifact structure-reactivity relationship often observed with these reactives.
    • Rishton G.M. Reactive compounds and in vitro false positives in HTS. Drug Discov Today 2 (1997) 382-384. Identifies protein-reactive functional groups as covalent-acting false positives in biochemical assays and also characterizes the artifact structure-reactivity relationship often observed with these reactives.
    • (1997) Drug Discov Today , vol.2 , pp. 382-384
    • Rishton, G.M.1
  • 6
    • 0037439447 scopus 로고    scopus 로고
    • Nonleadlikeness and leadlikeness in biochemical screening
    • Summary review of artifact-generating agents in biochemical screening and an introductory summary of leadlikeness properties.
    • Rishton G.M. Nonleadlikeness and leadlikeness in biochemical screening. Drug Discov. Today 8 (2003) 86-96. Summary review of artifact-generating agents in biochemical screening and an introductory summary of leadlikeness properties.
    • (2003) Drug Discov. Today , vol.8 , pp. 86-96
    • Rishton, G.M.1
  • 8
    • 0141792701 scopus 로고    scopus 로고
    • A specific mechanism of nonspecific inhibition
    • Summary of compound classes prone to aggregation and artifact data generation across multiple assays and featuring physical methods to detect aggregates.
    • McGovern S.L., Helfand B.T., Feng B., and Shoichet B.K. A specific mechanism of nonspecific inhibition. J Med Chem 46 (2003) 4265-4272. Summary of compound classes prone to aggregation and artifact data generation across multiple assays and featuring physical methods to detect aggregates.
    • (2003) J Med Chem , vol.46 , pp. 4265-4272
    • McGovern, S.L.1    Helfand, B.T.2    Feng, B.3    Shoichet, B.K.4
  • 9
    • 0141923641 scopus 로고    scopus 로고
    • Identification and prediction of promiscuous aggregating inhibitors among known drugs
    • Important demonstration that druglike compounds and even known drugs can aggregate in biochemical assays and result in artifact data.
    • Seidler J., McGovern S.L., Doman T.N., and Shoichet B.K. Identification and prediction of promiscuous aggregating inhibitors among known drugs. J Med Chem 46 (2003) 4477-4486. Important demonstration that druglike compounds and even known drugs can aggregate in biochemical assays and result in artifact data.
    • (2003) J Med Chem , vol.46 , pp. 4477-4486
    • Seidler, J.1    McGovern, S.L.2    Doman, T.N.3    Shoichet, B.K.4
  • 10
    • 0037431421 scopus 로고    scopus 로고
    • Kinase inhibitors: not just for kinases anymore
    • McGovern S.L., and Shoichet B.K. Kinase inhibitors: not just for kinases anymore. J Med Chem 46 (2003) 1478-1483
    • (2003) J Med Chem , vol.46 , pp. 1478-1483
    • McGovern, S.L.1    Shoichet, B.K.2
  • 11
    • 33645665186 scopus 로고    scopus 로고
    • Synergy and antagonism of promiscuous inhibition in multiple-compound mixtures
    • Feng B.Y., and Shoichet B.K. Synergy and antagonism of promiscuous inhibition in multiple-compound mixtures. J Med Chem 49 (2006) 2151-2154
    • (2006) J Med Chem , vol.49 , pp. 2151-2154
    • Feng, B.Y.1    Shoichet, B.K.2
  • 12
    • 33745188660 scopus 로고    scopus 로고
    • Screening in a spirit haunted world
    • Shoichet B.K. Screening in a spirit haunted world. Drug Discov Today 11 (2006) 607-615
    • (2006) Drug Discov Today , vol.11 , pp. 607-615
    • Shoichet, B.K.1
  • 14
    • 33749623901 scopus 로고    scopus 로고
    • Leadlikeness and structural diversity of synthetic screening libraries
    • A rigorous computational analysis of the properties of compounds in the globally available screening collections in the context of leadlikeness.
    • Verheij H.J. Leadlikeness and structural diversity of synthetic screening libraries. Mol Divers 10 (2006) 377-388. A rigorous computational analysis of the properties of compounds in the globally available screening collections in the context of leadlikeness.
    • (2006) Mol Divers , vol.10 , pp. 377-388
    • Verheij, H.J.1
  • 15
    • 33749628876 scopus 로고    scopus 로고
    • Managing, profiling and analyzing a library of 2.6 million compounds gathered from 32 chemical providers
    • Monge A., Arrault A., Marot C., and Morin-Allory L. Managing, profiling and analyzing a library of 2.6 million compounds gathered from 32 chemical providers. Mol Divers 10 (2006) 389-403
    • (2006) Mol Divers , vol.10 , pp. 389-403
    • Monge, A.1    Arrault, A.2    Marot, C.3    Morin-Allory, L.4
  • 16
    • 11844253252 scopus 로고    scopus 로고
    • ALARM NMR: A rapid and robust experimental method to detect reactive false positives in biochemical screens
    • Important development of a spectroscopic method to detect protein-reactive false positives.
    • Huth J.R., Mendoza R., Olejniczak E.T., Johnson R.W., Cothron D.A., Liu Y., Lerner C.G., Chen J., and Hajduk P.J. ALARM NMR: A rapid and robust experimental method to detect reactive false positives in biochemical screens. J Am Chem Soc 127 (2005) 217-224. Important development of a spectroscopic method to detect protein-reactive false positives.
    • (2005) J Am Chem Soc , vol.127 , pp. 217-224
    • Huth, J.R.1    Mendoza, R.2    Olejniczak, E.T.3    Johnson, R.W.4    Cothron, D.A.5    Liu, Y.6    Lerner, C.G.7    Chen, J.8    Hajduk, P.J.9
  • 17
    • 0035438391 scopus 로고    scopus 로고
    • Is there a difference between leads and drugs? A historical perspective
    • Seminal paper which suggests physiochemical properties of leads are significantly different than those properties of compounds considered to be druglike.
    • Oprea T.I., Davis A.M., Teague S.J., and Leeson P.D. Is there a difference between leads and drugs? A historical perspective. J Chem Inform Comp Sci 41 (2001) 1308-1315. Seminal paper which suggests physiochemical properties of leads are significantly different than those properties of compounds considered to be druglike.
    • (2001) J Chem Inform Comp Sci , vol.41 , pp. 1308-1315
    • Oprea, T.I.1    Davis, A.M.2    Teague, S.J.3    Leeson, P.D.4
  • 18
    • 2942564021 scopus 로고    scopus 로고
    • Pursuing the leadlikeness concept in pharmaceutical research
    • Further development of the leadlikeness concept and the physiochemical properties underpinning it.
    • Hann M.M., and Oprea T.I. Pursuing the leadlikeness concept in pharmaceutical research. Curr Opin Chem Biol 8 (2004) 255-263. Further development of the leadlikeness concept and the physiochemical properties underpinning it.
    • (2004) Curr Opin Chem Biol , vol.8 , pp. 255-263
    • Hann, M.M.1    Oprea, T.I.2
  • 20
    • 35748982934 scopus 로고    scopus 로고
    • The molecular libraries screening center network (MLSCN): Identifying chemical probes of biological systems
    • Huryn D.M., and Cosford N.D.P. The molecular libraries screening center network (MLSCN): Identifying chemical probes of biological systems. Ann Rep Med Chem 42 (2007) 401-416
    • (2007) Ann Rep Med Chem , vol.42 , pp. 401-416
    • Huryn, D.M.1    Cosford, N.D.P.2
  • 21
    • 8444225024 scopus 로고    scopus 로고
    • Policy forum: molecular biology: NIH molecular libraries initiative
    • Austin C.P., Brady L.S., Insel T.R., and Collins F.S. Policy forum: molecular biology: NIH molecular libraries initiative. Science 306 5699 (2004) 1138-1139
    • (2004) Science , vol.306 , Issue.5699 , pp. 1138-1139
    • Austin, C.P.1    Brady, L.S.2    Insel, T.R.3    Collins, F.S.4
  • 22
    • 33749651885 scopus 로고    scopus 로고
    • Roadmap or roadkill: A pharmacologist's analysis of the NIH molecular libraries initiative
    • Lazo J.S. Roadmap or roadkill: A pharmacologist's analysis of the NIH molecular libraries initiative. Mol Interv 6 (2006) 240-243
    • (2006) Mol Interv , vol.6 , pp. 240-243
    • Lazo, J.S.1
  • 24
    • 46849117879 scopus 로고    scopus 로고
    • Fragment-based approaches to lead discovery
    • Wyss D.F., and Eaton H.L. Fragment-based approaches to lead discovery. Front Drug Des Discov 3 (2007) 171-202
    • (2007) Front Drug Des Discov , vol.3 , pp. 171-202
    • Wyss, D.F.1    Eaton, H.L.2
  • 25
    • 34447648367 scopus 로고    scopus 로고
    • Fragment-based drug design: combining philosophy with technology
    • Bartoli S., Fincham C.I., and Fattori D. Fragment-based drug design: combining philosophy with technology. Curr Opin Drug Discov Dev 10 (2007) 422-429
    • (2007) Curr Opin Drug Discov Dev , vol.10 , pp. 422-429
    • Bartoli, S.1    Fincham, C.I.2    Fattori, D.3
  • 26
    • 33847381100 scopus 로고    scopus 로고
    • A decade of fragment-based drug design: strategic advances and lessons learned
    • Hajduk P.J., and Greer J. A decade of fragment-based drug design: strategic advances and lessons learned. Nat Rev Drug Discov 6 (2007) 211-219
    • (2007) Nat Rev Drug Discov , vol.6 , pp. 211-219
    • Hajduk, P.J.1    Greer, J.2
  • 27
    • 0029836953 scopus 로고    scopus 로고
    • Discovering high-affinity ligands for proteins: SAR by NMR
    • Introduction of fragment-based screening concept and spectroscopic assay development.
    • Shuker S.B., Hajduk P.J., Meadows R.P., and Fesik S.W. Discovering high-affinity ligands for proteins: SAR by NMR. Science 274 5292 (1996) 1531-1534. Introduction of fragment-based screening concept and spectroscopic assay development.
    • (1996) Science , vol.274 , Issue.5292 , pp. 1531-1534
    • Shuker, S.B.1    Hajduk, P.J.2    Meadows, R.P.3    Fesik, S.W.4
  • 28
    • 34447298280 scopus 로고    scopus 로고
    • SAR by NMR: an analysis of potency gains realized through fragment-linking and fragment-elaboration strategies for lead generation
    • Hajduk P.J., Huth J.R., and Sun C. SAR by NMR: an analysis of potency gains realized through fragment-linking and fragment-elaboration strategies for lead generation. Methods Princ Med Chem 34 (2006) 181-192
    • (2006) Methods Princ Med Chem , vol.34 , pp. 181-192
    • Hajduk, P.J.1    Huth, J.R.2    Sun, C.3
  • 29
    • 0037256186 scopus 로고    scopus 로고
    • Design of small molecule libraries for NMR screening and other applications in drug discovery
    • Jacoby E., Davies J., and Blommers M.J.J. Design of small molecule libraries for NMR screening and other applications in drug discovery. Curr Top Med Chem 3 (2003) 11-23
    • (2003) Curr Top Med Chem , vol.3 , pp. 11-23
    • Jacoby, E.1    Davies, J.2    Blommers, M.J.J.3
  • 30
    • 0035324944 scopus 로고    scopus 로고
    • Molecular complexity and its impact on the probability of finding leads for drug discovery
    • Hann M.M., Leach A.R., and Harper G. Molecular complexity and its impact on the probability of finding leads for drug discovery. J Chem Inform Comput Sci 41 (2001) 856-864
    • (2001) J Chem Inform Comput Sci , vol.41 , pp. 856-864
    • Hann, M.M.1    Leach, A.R.2    Harper, G.3
  • 31
    • 49949152506 scopus 로고    scopus 로고
    • Lead discovery and the concepts of complexity and lead-likeness in the evolution of drug candidates
    • Hann M.M., Leach A.R., Burrows J.N., and Griffen E. Lead discovery and the concepts of complexity and lead-likeness in the evolution of drug candidates. Compr Med Chem II 4 (2006) 435-458
    • (2006) Compr Med Chem II , vol.4 , pp. 435-458
    • Hann, M.M.1    Leach, A.R.2    Burrows, J.N.3    Griffen, E.4
  • 33
    • 33749659675 scopus 로고    scopus 로고
    • SAR by NMR: putting the pieces together
    • Hajduk P.J. SAR by NMR: putting the pieces together. Mol Interv 6 (2006) 266-272
    • (2006) Mol Interv , vol.6 , pp. 266-272
    • Hajduk, P.J.1
  • 34
    • 33751076241 scopus 로고    scopus 로고
    • Deconstructing fragment-based inhibitor discovery
    • Babaoglu K., Shoichet, and Brian B.K. Deconstructing fragment-based inhibitor discovery. Nat Chem Biol 2 (2006) 720-723
    • (2006) Nat Chem Biol , vol.2 , pp. 720-723
    • Babaoglu, K.1    Shoichet2    Brian, B.K.3
  • 35
    • 33750464876 scopus 로고    scopus 로고
    • Small molecule natural products in the discovery of therapeutic agents: the synthesis connection
    • Wilson R.M., and Danishefsky S.J. Small molecule natural products in the discovery of therapeutic agents: the synthesis connection. J Org Chem 71 (2006) 8329-8351
    • (2006) J Org Chem , vol.71 , pp. 8329-8351
    • Wilson, R.M.1    Danishefsky, S.J.2
  • 36
    • 49949152314 scopus 로고    scopus 로고
    • Chemically conditioned extracts of ginger oil: Leadlike 'alkaloidal' compounds derived from natural extracts via reductive amination
    • Anaheim, CA, United States, January 22-25 WRM-351
    • Arai H., Beierle K., Fullenwider C., Kai Z., and Rishton G.M. Chemically conditioned extracts of ginger oil: Leadlike 'alkaloidal' compounds derived from natural extracts via reductive amination. Abstracts, 40th Western Regional Meeting of the American Chemical Society. Anaheim, CA, United States, January 22-25 (2006) WRM-351
    • (2006) Abstracts, 40th Western Regional Meeting of the American Chemical Society
    • Arai, H.1    Beierle, K.2    Fullenwider, C.3    Kai, Z.4    Rishton, G.M.5
  • 37
    • 4444262413 scopus 로고    scopus 로고
    • A minimalist approach to fragment-based ligand design using common rings and linkers: Application to kinase inhibitors
    • Aronov A.M., and Bemis G.W. A minimalist approach to fragment-based ligand design using common rings and linkers: Application to kinase inhibitors. Proteins: Struct, Funct Bioinform 57 (2004) 36-50
    • (2004) Proteins: Struct, Funct Bioinform , vol.57 , pp. 36-50
    • Aronov, A.M.1    Bemis, G.W.2
  • 38
    • 33748299124 scopus 로고    scopus 로고
    • Efficient enantioselective synthesis of orthogonally protected (R)-α-alkylserines compatible with the solid phase peptide synthesis
    • Vassiliou S., Yiotakis A., and Magriotis P.A. Efficient enantioselective synthesis of orthogonally protected (R)-α-alkylserines compatible with the solid phase peptide synthesis. Tetrahedron Lett 47 (2006) 7339-7341
    • (2006) Tetrahedron Lett , vol.47 , pp. 7339-7341
    • Vassiliou, S.1    Yiotakis, A.2    Magriotis, P.A.3
  • 39
    • 0026000578 scopus 로고
    • Enantioselective synthesis of 2,3-diamino acids by the bislactim ether method
    • Hartwig W., and Mittendorf J. Enantioselective synthesis of 2,3-diamino acids by the bislactim ether method. Synthesis 11 (1991) 939-941
    • (1991) Synthesis , vol.11 , pp. 939-941
    • Hartwig, W.1    Mittendorf, J.2
  • 40
    • 0038208359 scopus 로고    scopus 로고
    • Synthesis of orthogonally protected (R)- and (S)-2-methylcysteine via an enzymatic desymmeterization and curtius rearrangement
    • Kedrowski B.L. Synthesis of orthogonally protected (R)- and (S)-2-methylcysteine via an enzymatic desymmeterization and curtius rearrangement. J Org Chem 68 (2003) 5403-5406
    • (2003) J Org Chem , vol.68 , pp. 5403-5406
    • Kedrowski, B.L.1
  • 41
    • 0036462501 scopus 로고    scopus 로고
    • A new approach to osmium-catalyzed asymmetric dihydroxylation and aminohydroxylation of olefins
    • Andersson M.A., Epple R., Fokin V.V., and Sharpless K.B. A new approach to osmium-catalyzed asymmetric dihydroxylation and aminohydroxylation of olefins. Agnew Chem Int Ed 41 (2002) 472-475
    • (2002) Agnew Chem Int Ed , vol.41 , pp. 472-475
    • Andersson, M.A.1    Epple, R.2    Fokin, V.V.3    Sharpless, K.B.4
  • 42
    • 0033550526 scopus 로고    scopus 로고
    • Asymmetric synthesis of the α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines
    • Cogan D.A., and Ellman J.A. Asymmetric synthesis of the α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines. J Am Chem Soc 121 (1999) 268-269
    • (1999) J Am Chem Soc , vol.121 , pp. 268-269
    • Cogan, D.A.1    Ellman, J.A.2
  • 43
    • 31544434530 scopus 로고    scopus 로고
    • Recent developments in isocyanide based multicomponent reactions in applied chemistry
    • Domling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106 (2006) 17-89
    • (2006) Chem Rev , vol.106 , pp. 17-89
    • Domling, A.1
  • 44
    • 27844439456 scopus 로고    scopus 로고
    • Recent advances in heterocycle generation using the efficient Ugi multiple-component condensation reaction
    • Tempest P.A. Recent advances in heterocycle generation using the efficient Ugi multiple-component condensation reaction. Curr Opin Drug Discov Dev 8 (2005) 776-788
    • (2005) Curr Opin Drug Discov Dev , vol.8 , pp. 776-788
    • Tempest, P.A.1
  • 45
    • 0037238724 scopus 로고    scopus 로고
    • Multi-component reactions: emerging chemistry in drug discovery from xylocain to crixivan
    • Hulme C., and Gore V. Multi-component reactions: emerging chemistry in drug discovery from xylocain to crixivan. Curr Med Chem 10 (2003) 51-80
    • (2003) Curr Med Chem , vol.10 , pp. 51-80
    • Hulme, C.1    Gore, V.2
  • 46
    • 4644282927 scopus 로고    scopus 로고
    • A novel intramolecular hydrogen bonding between a side-chain pyridine ring and an amide hydrogen of the peptide backbone in tripeptides containing the new amino acid, α,α-di(2-pyridyl)glycine
    • Yamada T., Ichino T., Hanyu M., Ninomiya D., Yanagihara R., Miyazawa T., and Murashima T. A novel intramolecular hydrogen bonding between a side-chain pyridine ring and an amide hydrogen of the peptide backbone in tripeptides containing the new amino acid, α,α-di(2-pyridyl)glycine. Org Biomol Chem 2 (2004) 2335-2339
    • (2004) Org Biomol Chem , vol.2 , pp. 2335-2339
    • Yamada, T.1    Ichino, T.2    Hanyu, M.3    Ninomiya, D.4    Yanagihara, R.5    Miyazawa, T.6    Murashima, T.7
  • 47
    • 0030607141 scopus 로고    scopus 로고
    • Use of solid supported nucleophiles and electrophiles for the purification of non-peptide small molecule libraries
    • Kaldor S.W., Siegel M.G., Fritz J.E., Dressman B.A., and Hahn P.J. Use of solid supported nucleophiles and electrophiles for the purification of non-peptide small molecule libraries. Tetrahedron Lett 37 (1996) 7193-7196
    • (1996) Tetrahedron Lett , vol.37 , pp. 7193-7196
    • Kaldor, S.W.1    Siegel, M.G.2    Fritz, J.E.3    Dressman, B.A.4    Hahn, P.J.5
  • 48
    • 0030987922 scopus 로고    scopus 로고
    • Polymer-supported quenching reagents for parallel purification
    • Booth R.J., and Hodges J.C. Polymer-supported quenching reagents for parallel purification. J Am Chem Soc 119 (1997) 4882-4886
    • (1997) J Am Chem Soc , vol.119 , pp. 4882-4886
    • Booth, R.J.1    Hodges, J.C.2
  • 49
    • 0036007207 scopus 로고    scopus 로고
    • Work-up strategies for high-throughput solution synthesis
    • Cork D., and Hird N. Work-up strategies for high-throughput solution synthesis. Drug Discov Today 7 (2002) 56-63
    • (2002) Drug Discov Today , vol.7 , pp. 56-63
    • Cork, D.1    Hird, N.2


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