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Volumn 52, Issue 21, 2009, Pages 6752-6756

Escape from flatland: Increasing saturation as an approach to improving clinical success

Author keywords

[No Author keywords available]

Indexed keywords

CARBON;

EID: 71049126548     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm901241e     Document Type: Article
Times cited : (2833)

References (41)
  • 1
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 2
    • 0037030653 scopus 로고    scopus 로고
    • Molecular properties that influence the oral bioavailability of drug candidates
    • Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 2002, 45, 2615-2623.
    • (2002) J. Med. Chem. , vol.45 , pp. 2615-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.-Y.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 3
    • 39749181550 scopus 로고    scopus 로고
    • Generation of a set of simple, interpretable ADMET rules of thumb
    • Gleeson, M. P. Generation of a set of simple, interpretable ADMET rules of thumb. J. Med. Chem. 2008, 51, 817-834.
    • (2008) J. Med. Chem. , vol.51 , pp. 817-834
    • Gleeson, M.P.1
  • 4
    • 18244370266 scopus 로고    scopus 로고
    • A bioavailability score
    • Martin, Y. C. A bioavailability score. J. Med. Chem. 2005, 48, 3164-3170.
    • (2005) J. Med. Chem. , vol.48 , pp. 3164-3170
    • Martin, Y.C.1
  • 5
    • 25844495011 scopus 로고    scopus 로고
    • Medicinal chemical properties of successful central nervous system drugs
    • DOI 10.1602/neurorx.2.4.541
    • Pajouhesh, H.; Lenz, G. R. Medicinal chemical properties of successful central nervous system drugs. NeuroRx 2005, 2, 541-553. (Pubitemid 41393264)
    • (2005) NeuroRx , vol.2 , Issue.4 , pp. 541-553
    • Pajouhesh, H.1    Lenz, G.R.2
  • 6
    • 14144251136 scopus 로고    scopus 로고
    • Exploring new chemical space by stereocontrolled diversity-oriented synthesis
    • Arya, P.; Joseph, R.; Gan, Z.; Rakic, B. Exploring new chemical space by stereocontrolled diversity-oriented synthesis. Chem. Biol. 2005, 12, 163-180.
    • (2005) Chem. Biol. , vol.12 , pp. 163-180
    • Arya, P.1    Joseph, R.2    Gan, Z.3    Rakic, B.4
  • 7
    • 58149346448 scopus 로고    scopus 로고
    • Synthesis of natural-product-like molecules with over eighty distinct scaffolds
    • Morton, D.; Leach, S.; Cordier, C.; Warriner, S.; Nelson, A. Synthesis of natural-product-like molecules with over eighty distinct scaffolds. Angew. Chem., Int. Ed. 2009, 48, 104-109.
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 104-109
    • Morton, D.1    Leach, S.2    Cordier, C.3    Warriner, S.4    Nelson, A.5
  • 8
    • 3042799070 scopus 로고    scopus 로고
    • A planning strategy for diversity-oriented synthesis
    • Burke, M. D.; Schreiber, S. L. A planning strategy for diversity-oriented synthesis. Angew. Chem., Int. Ed. 2004, 43, 46-58.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 46-58
    • Burke, M.D.1    Schreiber, S.L.2
  • 9
    • 0034678033 scopus 로고    scopus 로고
    • Target-oriented and diversity-oriented organic synthesis in drug discovery
    • DOI 10.1126/science.287.5460.1964
    • Schreiber, S. L. Target-oriented and diversity-oriented organic synthesis in drug discovery. Science 2000, 287, 1964-1969. (Pubitemid 30158663)
    • (2000) Science , vol.287 , Issue.5460 , pp. 1964-1969
    • Schreiber, S.L.1
  • 10
    • 33644839988 scopus 로고    scopus 로고
    • Diversity-oriented synthesis: Exploring the intersections between chemistry and biology
    • Tan, D., S. Diversity-oriented synthesis: exploring the intersections between chemistry and biology. Nat. Chem. Biol. 2005, 1, 74-84.
    • (2005) Nat. Chem. Biol. , vol.1 , pp. 74-84
    • Tan, D.S.1
  • 11
    • 0000524226 scopus 로고
    • The first general index of molecular complexity
    • Bertz, S. H. The first general index of molecular complexity. J. Am. Chem. Soc. 1981, 103, 3599-3601.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3599-3601
    • Bertz, S.H.1
  • 12
    • 0035272913 scopus 로고    scopus 로고
    • A New and simple approach to chemical complexity. application to the synthesis of natural products
    • Barone, R.; Chanon, M. A New and simple approach to chemical complexity. application to the synthesis of natural products. J. Chem. Inf. Comp. Sci. 2001, 41, 269-272.
    • (2001) J. Chem. Inf. Comp. Sci. , vol.41 , pp. 269-272
    • Barone, R.1    Chanon, M.2
  • 13
    • 26944499418 scopus 로고    scopus 로고
    • Rapid evaluation of synthetic and molecular complexity for in silico chemistry
    • Allu, T. K.; Oprea, T. I. Rapid evaluation of synthetic and molecular complexity for in silico chemistry. J. Chem. Inf. Mod. 2005, 45, 1237-1243.
    • (2005) J. Chem. Inf. Mod. , vol.45 , pp. 1237-1243
    • Allu, T.K.1    Oprea, T.I.2
  • 14
    • 0038170311 scopus 로고    scopus 로고
    • Similarity metrics for ligands reflecting the similarity of the target proteins
    • Schuffenhauer, A.; Floersheim, P.; Acklin, P.; Jacoby, E. Similarity metrics for ligands reflecting the similarity of the target proteins. J. Chem. Inf. Comp. Sci. 2003, 43, 391-405.
    • (2003) J. Chem. Inf. Comp. Sci. , vol.43 , pp. 391-405
    • Schuffenhauer, A.1    Floersheim, P.2    Acklin, P.3    Jacoby, E.4
  • 15
    • 33646237094 scopus 로고    scopus 로고
    • Relationships between molecular complexity, biological activity, and structural diversity
    • Schuffenhauer, A.; Brown, N.; Selzer, P.; Ertl, P.; Jacoby, E. Relationships between molecular complexity, biological activity, and structural diversity. J. Chem. Inf. Mod. 2006, 46, 525-535.
    • (2006) J. Chem. Inf. Mod. , vol.46 , pp. 525-535
    • Schuffenhauer, A.1    Brown, N.2    Selzer, P.3    Ertl, P.4    Jacoby, E.5
  • 17
    • 33845364148 scopus 로고    scopus 로고
    • Fragment-based drug design: How big is too big?
    • Hajduk, P. J. Fragment-based drug design: how big is too big? J. Med. Chem. 2006, 49, 6972-6976.
    • (2006) J. Med. Chem. , vol.49 , pp. 6972-6976
    • Hajduk, P.J.1
  • 18
    • 0037208308 scopus 로고    scopus 로고
    • Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry
    • Feher, M.; Schmidt, J. M. Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J. Chem. Inf. Comp. Sci. 2003, 43, 218-227.
    • (2003) J. Chem. Inf. Comp. Sci. , vol.43 , pp. 218-227
    • Feher, M.1    Schmidt, J.M.2
  • 19
    • 0032546782 scopus 로고    scopus 로고
    • Pi-stacking interactions: Alive and well in proteins
    • McGaughey, G. B.; Gagne, M.; Rappe, A. K. Pi-stacking interactions: alive and well in proteins. J. Biol. Chem. 1998, 273, 15458-15463.
    • (1998) J. Biol. Chem. , vol.273 , pp. 15458-15463
    • McGaughey, G.B.1    Gagne, M.2    Rappe, A.K.3
  • 20
    • 0030043489 scopus 로고    scopus 로고
    • Cation-pi interactions in chemistry and biology: A new view of benzene, Phe, Tyr, and Trp
    • Dougherty, D. A. Cation-pi interactions in chemistry and biology: a new view of benzene, phe, tyr, and trp. Science 1996, 271, 163-168. (Pubitemid 26033294)
    • (1996) Science , vol.271 , Issue.5246 , pp. 163-168
    • Dougherty, D.A.1
  • 21
    • 33846356275 scopus 로고    scopus 로고
    • Property-based drug design and preformulation
    • Lippincott, Williams and Witkins; Philadelphia
    • Ando, H. Y.; Radebaugh, G. W., Property-based drug design and preformulation. In Remington: The Science and Practice of Pharmacy; Lippincott, Williams and Witkins; Philadelphia, 2005; pp 720-744.
    • (2005) Remington: The Science and Practice of Pharmacy , pp. 720-744
    • Ando, H.Y.1    Radebaugh, G.W.2
  • 22
    • 2942704243 scopus 로고    scopus 로고
    • ESOL: Estimating aqueous solubility directly from molecular structure
    • Delaney, J. S. ESOL: estimating aqueous solubility directly from molecular structure. J. Chem. Inf. Comp. Sci. 2004, 44, 1000-1005.
    • (2004) J. Chem. Inf. Comp. Sci. , vol.44 , pp. 1000-1005
    • Delaney, J.S.1
  • 23
    • 44049092515 scopus 로고    scopus 로고
    • Straightforward recursive partitioning model for discarding insoluble compounds in the drug discovery process
    • Lamanna, C.; Bellini, M.; Padova, A.; Westerberg, G.; Maccari, L. Straightforward recursive partitioning model for discarding insoluble compounds in the drug discovery process. J. Med. Chem. 2008, 51, 2891-2897.
    • (2008) J. Med. Chem. , vol.51 , pp. 2891-2897
    • Lamanna, C.1    Bellini, M.2    Padova, A.3    Westerberg, G.4    Maccari, L.5
  • 25
    • 0037468884 scopus 로고    scopus 로고
    • A comparison of physiochemical property profiles of development and marketed oral drugs
    • Wenlock, M. C.; Austin, R. P.; Barton, P.; Davis, A. M.; Leeson, P. D. A comparison of physiochemical property profiles of development and marketed oral drugs. J. Med. Chem. 2003, 46, 1250-1256.
    • (2003) J. Med. Chem. , vol.46 , pp. 1250-1256
    • Wenlock, M.C.1    Austin, R.P.2    Barton, P.3    Davis, A.M.4    Leeson, P.D.5
  • 26
    • 71049134458 scopus 로고    scopus 로고
    • GVK Bio web site [online]
    • GVK Bio web site [online], http://www.gvkbio.com/Informatics.html/.
  • 27
    • 71049138992 scopus 로고    scopus 로고
    • note
    • Some compounds did not have a publication date recorded and these were kept in the analysis: 28 phase 1, 50 phase 2 and 10 phase 3.
  • 28
    • 71049195394 scopus 로고    scopus 로고
    • Pipeline Pilot is available from Accelrys
    • Pipeline Pilot is available from Accelrys, http://accelrys.com/products/ scitegic/.
  • 29
    • 71049179896 scopus 로고    scopus 로고
    • JMP is available from
    • JMP is available from http://www.jmp.com/.
  • 30
    • 1542741028 scopus 로고    scopus 로고
    • ADME evaluation in drug discovery. 4. Prediction of aqueous solubility based on atom contribution approach
    • Hou, T. J.; Xia, K.; Zhang, W.; Xu, X. J. ADME evaluation in drug discovery. 4. Prediction of aqueous solubility based on atom contribution approach. J. Chem. Inf. Comp. Sci. 2003, 44, 266-275.
    • (2003) J. Chem. Inf. Comp. Sci. , vol.44 , pp. 266-275
    • Hou, T.J.1    Xia, K.2    Zhang, W.3    Xu, X.J.4
  • 31
    • 20444362720 scopus 로고    scopus 로고
    • General melting point prediction based on a diverse compound data set and artificial neural networks
    • Karthikeyan, M.; Glen, R. C.; Bender, A. General melting point prediction based on a diverse compound data set and artificial neural networks. J. Chem. Inf. Mod. 2005, 45, 581-590.
    • (2005) J. Chem. Inf. Mod. , vol.45 , pp. 581-590
    • Karthikeyan, M.1    Glen, R.C.2    Bender, A.3
  • 32
    • 0019166075 scopus 로고
    • Solubility and partitioning I: Solubility of nonelectrolytes in water
    • Yalkowsky, S. H.; Valvani, S. C. Solubility and partitioning I: Solubility of nonelectrolytes in water. J. Pharm. Sci. 1980, 69, 912-922.
    • (1980) J. Pharm. Sci. , vol.69 , pp. 912-922
    • Yalkowsky, S.H.1    Valvani, S.C.2
  • 33
    • 0035138216 scopus 로고    scopus 로고
    • Estimation of the aqueous solubility I: Application to organic nonelectrolytes
    • Neera, J.; Samuel, H. Y. Estimation of the aqueous solubility I: Application to organic nonelectrolytes. J. Pharm. Sci. 2001, 90, 234-252.
    • (2001) J. Pharm. Sci. , vol.90 , pp. 234-252
    • Neera, J.1    Samuel, H.Y.2
  • 34
  • 35
    • 67349254634 scopus 로고    scopus 로고
    • An interesting relationship between drug absorption and melting point
    • Chu, K. A.; Yalkowsky, S. H. An interesting relationship between drug absorption and melting point. Int. J. Pharm. 2009, 373, 24-40.
    • (2009) Int. J. Pharm. , vol.373 , pp. 24-40
    • Chu, K.A.1    Yalkowsky, S.H.2
  • 37
    • 0037112673 scopus 로고    scopus 로고
    • Palladium-catalyzed coupling reactions of aryl chlorides
    • DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
    • Adam, F. L.; Gregory, C. F. Palladium-catalyzed coupling reactions of aryl chlorides. Angew. Chem., Int. Ed. 2002, 41, 4176-4211. (Pubitemid 35402094)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.22 , pp. 4176-4211
    • Littke, A.F.1    Fu, G.C.2
  • 38
    • 3042654141 scopus 로고    scopus 로고
    • A rationally designed universal catalyst for suzuki-miyaura coupling processes13
    • Shawn, D. W.; Timothy, E. B.; Joseph, R. M.; Stephen, L. B. A rationally designed universal catalyst for suzuki-miyaura coupling processes13. Angew. Chem., Int. Ed. 2004, 43, 1871-1876.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1871-1876
    • Shawn, D.W.1    Timothy, E.B.2    Joseph, R.M.3    Stephen, L.B.4
  • 39
    • 0038579438 scopus 로고    scopus 로고
    • Expanding Pd-Catalyzed Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions
    • Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. Expanding Pd-Catalyzed Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions. J. Am. Chem. Soc. 2003, 125, 6653-6655.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6653-6655
    • Huang, X.1    Anderson, K.W.2    Zim, D.3    Jiang, L.4    Klapars, A.5    Buchwald, S.L.6
  • 40
    • 0013157111 scopus 로고    scopus 로고
    • Pd-catalyzed N-arylation of heteroarylamines
    • Yin, J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M. Pd-catalyzed N-arylation of heteroarylamines. Org. Lett. 2002, 4, 3481-3484.
    • (2002) Org. Lett. , vol.4 , pp. 3481-3484
    • Yin, J.1    Zhao, M.M.2    Huffman, M.A.3    McNamara, J.M.4
  • 41
    • 70350409235 scopus 로고    scopus 로고
    • The impact of aromatic ring count on compound developability - Are too many aromatic rings a liability in drug design
    • doi:10.1016/j.drudis.2009.07.014
    • Ritchie, T. J.; Macdonald, S. J. F. The impact of aromatic ring count on compound developability - are too many aromatic rings a liability in drug design. Drug Disc. Today 2009, doi:10.1016/j.drudis.2009.07.014.
    • (2009) Drug Disc. Today
    • Ritchie, T.J.1    Macdonald, S.J.F.2


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