메뉴 건너뛰기




Volumn 54, Issue 6, 2011, Pages 1539-1554

Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry

Author keywords

[No Author keywords available]

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; 2,3,7,8 TETRACHLORODIBENZOFURAN; 3 METHYLCHOLANTHRENE; 7 CHLORO 2,3 DIHYDRO 2(PHENYL)PYRIDAZINO[4,5 B]QUINOLINE 1,4,10 (5H) TRIONES; AMG 157; ANILIDE; AROMATIC HYDROCARBON RECEPTOR; BENZAMIDE; BENZENESULFONIC ACID DERIVATIVE; BENZO[A]PYRENE; BETA NAPHTHOFLAVONE; CARBANILAMIDE; CARBOXYL GROUP; CARBOXYLIC ACID DERIVATIVE; CIPROFLOXACIN; CYCLIN DEPENDENT KINASE INHIBITOR; DIPYRONE; FLUORINE; GYRASE INHIBITOR; MACROPHAGE ELASTASE; MATRIX METALLOPROTEINASE INHIBITOR; N [4 [6 [4 (TRIFLUOROMETHYL)PHENYL] 4 PYRIMIDINYLOXY]BENZOTHIAZOL 2 YL]ACETAMIDE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR DELTA AGONIST; PIPERIDINE DERIVATIVE; PROTEIN KINASE INHIBITOR; QUINOLINE DERIVATIVE; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANILLOID RECEPTOR 1 ANTAGONIST; VITRONECTIN RECEPTOR BLOCKING AGENT;

EID: 79952804851     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101356p     Document Type: Article
Times cited : (477)

References (80)
  • 1
    • 0028948839 scopus 로고
    • A Theoretical Basis for a Biopharmaceutic Drug Classification: The Correlation of in Vitro Drug Product Dissolution and in Vivo Bioavailability
    • Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. A Theoretical Basis for a Biopharmaceutic Drug Classification: The Correlation of in Vitro Drug Product Dissolution and In Vivo Bioavailability Pharm. Res. 1995, 12, 413-420
    • (1995) Pharm. Res. , vol.12 , pp. 413-420
    • Amidon, G.L.1    Lennernas, H.2    Shah, V.P.3    Crison, J.R.4
  • 4
    • 33749994108 scopus 로고    scopus 로고
    • Solubility: It's not just for physical chemists
    • DOI 10.1016/j.drudis.2006.09.002, PII S1359644606003643
    • Bhattachar, S. N.; Deschenes, L. A.; Wesley, J. A. Solubility: It's Not Just for Physical Chemists Drug Discovery Today 2006, 11, 1012-1018 (Pubitemid 44572881)
    • (2006) Drug Discovery Today , vol.11 , Issue.21-22 , pp. 1012-1018
    • Bhattachar, S.N.1    Deschenes, L.A.2    Wesley, J.A.3
  • 5
    • 79952787384 scopus 로고    scopus 로고
    • note
    • In this review, we define thermodynamic solubility as the solubility obtained after a solid compound has been agitated in the solvent for more than 24 h.
  • 7
    • 77955915185 scopus 로고    scopus 로고
    • Strategies at the Interface of Drug Discovery and Development: Early Optimization of the Solid State Phase and Preclinical Toxicology Formulation for Potential Drug Candidates
    • Palucki, M.; Higgins, J. D.; Kwong, E.; Templeton, A. C. Strategies at the Interface of Drug Discovery and Development: Early Optimization of the Solid State Phase and Preclinical Toxicology Formulation for Potential Drug Candidates J. Med. Chem. 2010, 53, 5897-5905
    • (2010) J. Med. Chem. , vol.53 , pp. 5897-5905
    • Palucki, M.1    Higgins, J.D.2    Kwong, E.3    Templeton, A.C.4
  • 8
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • DOI 10.1016/S0169-409X(00)00129-0, PII S0169409X00001290
    • 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. 2001, 46, 3-26 (Pubitemid 33653411)
    • (2000) Advanced Drug Delivery Reviews , vol.46 , Issue.1-3 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 9
    • 0034461768 scopus 로고    scopus 로고
    • Drug-like properties and the causes of poor solubility and poor permeability
    • DOI 10.1016/S1056-8719(00)00107-6, PII S1056871900001076
    • Lipinski, C. A. Drug-like Properties and the Causes of Poor Solubility and Poor Permeability J. Pharmacol. Toxicol. Methods 2000, 44, 235-249 (Pubitemid 32239479)
    • (2000) Journal of Pharmacological and Toxicological Methods , vol.44 , Issue.1 , pp. 235-249
    • Lipinski, C.A.1
  • 10
    • 0001085722 scopus 로고
    • Linear Free-Energy Relationship between Partition Coefficients and the Aqueous Solubility of Organic Liquids
    • Hansch, C.; Quinlan, J. E.; Lawrence, G. L. Linear Free-Energy Relationship between Partition Coefficients and the Aqueous Solubility of Organic Liquids J. Org. Chem. 1968, 33, 347-350
    • (1968) J. Org. Chem. , vol.33 , pp. 347-350
    • Hansch, C.1    Quinlan, J.E.2    Lawrence, G.L.3
  • 11
    • 0019470712 scopus 로고
    • Solubility and partitioning IV: Aqueous solubility and octanol-water partition coefficients of liquid nonelectrolytes
    • DOI 10.1002/jps.2600700510
    • Valvani, S. C.; Yalkowsky, S. H.; Roseman, T. J. Solubility and Partitioning IV: Aqueous Solubility and Octanol-Water Partition Coefficients of Liquid Nonelectrolytes J. Pharm. Sci. 1981, 70, 502-507 (Pubitemid 11075795)
    • (1981) Journal of Pharmaceutical Sciences , vol.70 , Issue.5 , pp. 502-507
    • Valvani, S.C.1    Yalkowsky, S.H.2    Roseman, T.J.3
  • 12
    • 0018927965 scopus 로고
    • Water solubility and octanol/water partition coefficients of organics. Limitations of the solubility-partition coefficient correlation
    • DOI 10.1021/es60170a013
    • Banerjee, S; Yalkowsky, S. H; Valvani, S. C. Water Solubility and Octanol/Water Partition Coefficients of Organics: Limitations of the Solubility-Partition Coefficient Correlation Environ. Sci. Technol. 1980, 10, 1227-1229 (Pubitemid 10030051)
    • (1980) Environmental Science and Technology , vol.14 , Issue.10 , pp. 1227-1229
    • Banerjee, S.1    Yalkowsky, S.H.2    Valvani, S.C.3
  • 13
    • 0035138216 scopus 로고    scopus 로고
    • Estimation of the aqueous solubility I: Application to organic nonelectrolytes
    • DOI 10.1002/1520-6017(200102)90:2<234::AID-JPS14>3.0.CO;2-V
    • Jain, N.; Yalkowsky, S. H. Estimation of the Aqueous Solubility I: Application to Organic Nonelectrolytes J. Pharm. Sci. 2001, 90, 234-252 (Pubitemid 32158051)
    • (2001) Journal of Pharmaceutical Sciences , vol.90 , Issue.2 , pp. 234-252
    • Jain, N.1    Yalkowsky, S.H.2
  • 14
    • 0019166075 scopus 로고
    • Solubility and partitioning I: Solubility of nonelectrolytes in water
    • DOI 10.1002/jps.2600690814
    • Yalkowsky, S. H.; Valvani, S. C. Solubility and Partitioning I: Solubility of Non Electrolytes in Water J. Pharm. Sci. 1980, 69, 912-922 (Pubitemid 11234579)
    • (1980) Journal of Pharmaceutical Sciences , vol.69 , Issue.8 , pp. 912-922
    • Yalkowsky, S.H.1    Valvani, S.C.2
  • 15
    • 0035263415 scopus 로고    scopus 로고
    • Prediction of drug solubility by the general solubility equation (GSE)
    • DOI 10.1021/ci000338c
    • Ran, Y.; Yalkowsky, S. H. Prediction of Drug Solubility by the General Solubility Equation (GSE) J. Chem. Inf. Comput. Sci. 2001, 41, 354-357 (Pubitemid 32408650)
    • (2001) Journal of Chemical Information and Computer Sciences , vol.41 , Issue.2 , pp. 354-357
    • Ran, Y.1    Yalkowsky, S.H.2
  • 16
    • 0001410276 scopus 로고
    • Are Crystal Structures Predictable
    • Gavezzotti, A. Are Crystal Structures Predictable- Acc. Chem. Res. 1994, 27, 309-314
    • (1994) Acc. Chem. Res. , vol.27 , pp. 309-314
    • Gavezzotti, A.1
  • 17
    • 0003998388 scopus 로고
    • 72 nd ed.; CRC Press: Boca Raton, FL.
    • Handbook of Chemistry and Physics, 72 nd ed.; CRC Press: Boca Raton, FL, 1991.
    • (1991) Handbook of Chemistry and Physics
  • 18
    • 71049126548 scopus 로고    scopus 로고
    • Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success
    • Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success J. Med. Chem. 2009, 52, 6752-6756
    • (2009) J. Med. Chem. , vol.52 , pp. 6752-6756
    • Lovering, F.1    Bikker, J.2    Humblet, C.3
  • 19
    • 79952782718 scopus 로고
    • Water Solubility of PCB Isomers
    • Hoover, T. B. Water Solubility of PCB Isomers PCB Newsl. 1971, 3, 4-5
    • (1971) PCB Newsl. , vol.3 , pp. 4-5
    • Hoover, T.B.1
  • 20
    • 0018613260 scopus 로고
    • Solubility of polychlorinated biphenyls and capacitor fluid in water
    • DOI 10.1016/0043-1354(79)90169-6
    • Lee, M. C.; Chian, E. S. K.; Griffin, R. A. Solubility of Polychlorinated Biphenyls and Capacitor Fluid Water Water Res. 1979, 13, 1249-1258 (Pubitemid 10167175)
    • (1979) Water Research , vol.13 , Issue.12 , pp. 1249-1258
    • Lee, M.C.1    Chian, E.S.K.2    Griffin, R.A.3
  • 21
    • 37049075182 scopus 로고
    • Molecular Symmetry, Melting Temperatures and Melting Enthalpies of Substituted Benzenes and Naphthalenes
    • Gavezzotti, A. Molecular Symmetry, Melting Temperatures and Melting Enthalpies of Substituted Benzenes and Naphthalenes J. Chem. Soc., Perkin Trans. 2 1995, 1399-1404
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 1399-1404
    • Gavezzotti, A.1
  • 22
    • 0000602569 scopus 로고    scopus 로고
    • Estimation of Entropy of Melting from Molecular Structure: A Non-Group Contribution Method
    • Dannenfelser, R.-M.; Yalkowsky, S. H. Estimation of Entropy of Melting from Molecular Structure: A Non-Group Contribution Method Ind. Eng. Chem. Res. 1996, 35, 1483-1486 (Pubitemid 126460306)
    • (1996) Industrial and Engineering Chemistry Research , vol.35 , Issue.4 , pp. 1483-1486
    • Dannenfelser, R.-M.1    Yalkowsky, S.H.2
  • 23
    • 79952783519 scopus 로고    scopus 로고
    • Molecular Drug Properties: Measurement and Prediction
    • Mannhold, R., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany
    • Lipinski, C. A. In Molecular Drug Properties: Measurement and Prediction; Mannhold, R., Ed.; Methods and Principles in Medicinal Chemistry, Vol. 37; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008; pp 257 - 282.
    • (2008) Methods and Principles in Medicinal Chemistry , vol.37 , pp. 257-282
    • Lipinski, C.A.1    Mannhold, R.2
  • 24
    • 77649142032 scopus 로고    scopus 로고
    • Predicting Aqueous Solubility: The Role of Crystallinity
    • Chu, K. A.; Yalkowsky, S. H. Predicting Aqueous Solubility: The Role of Crystallinity Curr. Drug Metab. 2009, 10, 1184-1191
    • (2009) Curr. Drug Metab. , vol.10 , pp. 1184-1191
    • Chu, K.A.1    Yalkowsky, S.H.2
  • 25
    • 76649105413 scopus 로고    scopus 로고
    • Estimation of the Ideal Solubility (Crystal-Liquid Fugacity Ratio) of Organic Compounds
    • Yalkowsky, S. H.; Wu, M. Estimation of the Ideal Solubility (Crystal-Liquid Fugacity Ratio) of Organic Compounds J. Pharm. Sci. 2010, 99, 1100-1106
    • (2010) J. Pharm. Sci. , vol.99 , pp. 1100-1106
    • Yalkowsky, S.H.1    Wu, M.2
  • 29
    • 18644374475 scopus 로고    scopus 로고
    • Optimization of amide-based inhibitors of soluble epoxide hydrolase with improved water solubility
    • DOI 10.1021/jm0500929
    • Kim, I. H.; Heirtzler, F. R.; Morisseau, C.; Nishi, K.; Tsai, H. J.; Hammock, B. D. Optimization of Amide-Based Inhibitors of Soluble Epoxide Hydrolase with Improved Water Solubility J. Med. Chem. 2005, 48, 3621-3629 (Pubitemid 40664110)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.10 , pp. 3621-3629
    • Kim, I.-H.1    Heirtzler, F.R.2    Morisseau, C.3    Nishi, K.4    Tsai, H.-J.5    Hammock, B.D.6
  • 35
    • 0023903939 scopus 로고
    • Neutrophils as Potential Participants in Acute Myocardial Ischemia: Relevance to Reperfusion
    • Mehta, J. L.; Nichols, W. W.; Mehta, P. Neutrophils as Potential Participants in Acute Myocardial Ischemia: Relevance to Reperfusion J. Am. Coll. Cardiol. 1988, 11, 1309-1316
    • (1988) J. Am. Coll. Cardiol. , vol.11 , pp. 1309-1316
    • Mehta, J.L.1    Nichols, W.W.2    Mehta, P.3
  • 36
    • 0024598265 scopus 로고
    • Early in Reperfusion, Leukocytes Alter Perfused Coronary Capillarity and Vascular Resistance
    • Reynolds, J. M.; Mcdonagh, P. F. Early in Reperfusion, Leukocytes Alter Perfused Coronary Capillarity and Vascular Resistance Am. J. Physiol.: Heart Circ. Physiol. 1989, 256, H982-H989
    • (1989) Am. J. Physiol.: Heart Circ. Physiol. , vol.256
    • Reynolds, J.M.1    McDonagh, P.F.2
  • 39
    • 0027315841 scopus 로고
    • Site-directed mutagenesis of the arginine-glycine-aspartic acid in vitronectin abolishes cell adhesion
    • Cherny, R. C.; Honan, M. A.; Perumal, P. Site-Directed Mutagenesis of Arginine-Glycine Aspartic Acid in Vitronectin Abolishes Cell Adhesion J. Biol. Chem. 1993, 268, 9725-9729 (Pubitemid 23146033)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.13 , pp. 9725-9729
    • Cherny, R.C.1    Honan, M.A.2    Thiagarajan, P.3
  • 44
    • 2342635206 scopus 로고    scopus 로고
    • Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution
    • DOI 10.1016/j.chroma.2003.10.084, PII S0021967303019095
    • Valkó, K. Application of High-Performance Liquid Chromatography Based Measurements of Lipophilicity to Model Biological Distribution J. Chromatogr., A 2004, 1037, 299-310 (Pubitemid 38591346)
    • (2004) Journal of Chromatography A , vol.1037 , Issue.1-2 , pp. 299-310
    • Valko, K.1
  • 45
    • 79952813319 scopus 로고    scopus 로고
    • 3 Dual Antagonists
    • Torisawa, Y., Ed.; CMC Publishing: Tokyo
    • 3 Dual Antagonists. In Soyaku Shien Kenkyu no Tenbo; Torisawa, Y., Ed.; CMC Publishing: Tokyo, 2008; pp 3 - 13.
    • (2008) Soyaku Shien Kenkyu No Tenbo , pp. 3-13
    • Ishikawa, M.1    Ajito, K.2
  • 47
    • 19444383619 scopus 로고    scopus 로고
    • 3 and glycoprotein IIb/IIIa inhibition causes reduction in infarct size in a model of acute coronary thrombosis and primary angioplasty
    • DOI 10.1016/j.cardiores.2005.01.016, PII S0008636305000441
    • 3 and Glycoprotein IIb/IIIa Inhibition Causes Reduction in Infarct Size in a Model of Acute Coronary Thrombosis and Primary Angioplasty Cardiovasc. Res. 2005, 66, 552-561 (Pubitemid 40725767)
    • (2005) Cardiovascular Research , vol.66 , Issue.3 , pp. 552-561
    • Sakuma, T.1    Sari, I.2    Goodman, C.N.3    Lindner, J.R.4    Klibanov, A.L.5    Kaul, S.6
  • 48
    • 33747783554 scopus 로고    scopus 로고
    • Evaluating the 'no reflow' phenomenon with myocardial contrast echocardiography
    • DOI 10.1007/s00395-006-0618-z
    • Kaul, S. Evaluating the "No Reflow" Phenomenon with Myocardial Contrast Echocardiography Basic Res. Cardiol. 2006, 101, 391-399 (Pubitemid 44275872)
    • (2006) Basic Research in Cardiology , vol.101 , Issue.5 , pp. 391-399
    • Kaul, S.1
  • 49
    • 75149143486 scopus 로고    scopus 로고
    • -Naphthoflavone Analogs as Potent and Soluble Aryl Hydrocarbon Receptor Agonists: Improvement of Solubility by Disruption of Molecular Planarity
    • Fujita, Y.; Yonehara, M.; Tetsuhashi, M.; Noguchi-Yachide, T.; Hashimoto, Y.; Ishikawa, M. -Naphthoflavone Analogs as Potent and Soluble Aryl Hydrocarbon Receptor Agonists: Improvement of Solubility by Disruption of Molecular Planarity Bioorg. Med. Chem. 2010, 18, 1194-1203
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 1194-1203
    • Fujita, Y.1    Yonehara, M.2    Tetsuhashi, M.3    Noguchi-Yachide, T.4    Hashimoto, Y.5    Ishikawa, M.6
  • 51
    • 0037450429 scopus 로고    scopus 로고
    • Functional role of AhR in the expression of toxic effects by TCDD
    • DOI 10.1016/S0304-4165(02)00485-3, PII S0304416502004853
    • Mimura, J.; Fujii-Kuriyama, Y. Functional Role of AhR in the Expression of Toxic Effects by TCDD Biochim. Biophys. Acta 2003, 1619, 263-268 (Pubitemid 36160604)
    • (2003) Biochimica et Biophysica Acta - General Subjects , vol.1619 , Issue.3 , pp. 263-268
    • Mimura, J.1    Fujii-Kuriyama, Y.2
  • 52
    • 68949172534 scopus 로고    scopus 로고
    • The Aryl Hydrocarbon Receptor in Immunity
    • Esser, C.; Rannug, A.; Stockinger, B. The Aryl Hydrocarbon Receptor in Immunity Trends Immunol. 2009, 30, 447-454
    • (2009) Trends Immunol. , vol.30 , pp. 447-454
    • Esser, C.1    Rannug, A.2    Stockinger, B.3
  • 53
    • 0022671959 scopus 로고
    • Water Solubility of 2,3,7,8-Tetrachlorodibenzo-para-dioxin
    • Marple, L.; Brunck, R.; Throop, L. Water Solubility of 2,3,7,8-Tetrachlorodibenzo-para-dioxin Environ. Sci. Technol. 1986, 20, 180-182
    • (1986) Environ. Sci. Technol. , vol.20 , pp. 180-182
    • Marple, L.1    Brunck, R.2    Throop, L.3
  • 55
    • 66449102422 scopus 로고    scopus 로고
    • Genotoxicity of Environmentally Relevant Concentrations of Water-Soluble Oil Components in Cod (Gadus morhua)
    • Holth, T. F.; Beylich, B. A.; Skarphedinsdottir, H.; Liewenborg, B.; Grung, M.; Hylland, K. Genotoxicity of Environmentally Relevant Concentrations of Water-Soluble Oil Components in Cod (Gadus morhua) Environ. Sci. Technol. 2009, 43, 3329-3334
    • (2009) Environ. Sci. Tenhnol. , vol.43 , pp. 3329-3334
    • Holth, T.F.1    Beylich, B.A.2    Skarphedinsdottir, H.3    Liewenborg, B.4    Grung, M.5    Hylland, K.6
  • 57
    • 77957574845 scopus 로고    scopus 로고
    • Improvement of Water-Solubility of Biarylcarboxylic Acid Peroxisome Proliferator-Activated Receptor (PPAR) -Selective Partial Agonists by Disruption of Molecular Planarity/Symmetry
    • Kasuga, J.; Ishikawa, M; Yonehara, M.; Makishima, M.; Hashimoto, Y.; Miyachi, H. Improvement of Water-Solubility of Biarylcarboxylic Acid Peroxisome Proliferator-Activated Receptor (PPAR) -Selective Partial Agonists by Disruption of Molecular Planarity/Symmetry Bioorg. Med. Chem. 2010, 18, 7164-7173
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 7164-7173
    • Kasuga, J.1    Ishikawa, M.2    Yonehara, M.3    Makishima, M.4    Hashimoto, Y.5    Miyachi, H.6
  • 59
    • 36549038966 scopus 로고    scopus 로고
    • PPAR agonists: Multimodal drugs for the treatment of type-2 diabetes
    • DOI 10.1016/j.beem.2007.09.004, PII S1521690X07000887, New Therapies for Diabetes
    • Gross, B.; Staels, B. PPAR Agonists: Multimodal Drugs for the Treatment of Type-2 Diabete Best Pract. Res., Clin. Endocrinol. Metab. 2007, 21, 687-710 (Pubitemid 350177568)
    • (2007) Best Practice and Research in Clinical Endocrinology and Metabolism , vol.21 , Issue.4 , pp. 687-710
    • Gross, B.1    Staels, B.2
  • 68
    • 33750976700 scopus 로고    scopus 로고
    • Matched molecular pairs as a guide in the optimization of pharmaceutical properties; a study of aqueous solubility, plasma protein binding and oral exposure
    • DOI 10.1021/jm0605233
    • Leach, A. G.; Jones, H. D.; Cosgrove, D. A.; Kenny, P. W.; Ruston, L.; MacFaul, P.; Wood, J. M.; Colclough, N.; Law, B. Matched Molecular Pairs as a Guide in the Optimization of Pharmaceutical Properties: A Study of Aqueous Solubility, Plasma Protein Binding and Oral Exposure J. Med. Chem. 2006, 49, 6672-6682 (Pubitemid 44749735)
    • (2006) Journal of Medicinal Chemistry , vol.49 , Issue.23 , pp. 6672-6682
    • Leach, A.G.1    Jones, H.D.2    Cosgrove, D.A.3    Kenny, P.W.4    Ruston, L.5    MacFaul, P.6    Wood, J.M.7    Colclough, N.8    Law, B.9
  • 69
    • 56249112601 scopus 로고    scopus 로고
    • Imidazole Pyrimidine Amides as Potent, Orally Bioavailable Cyclin-Dependent Kinase Inhibitors
    • Jones, C. D.; Andrews., D. M.; Barker, A. J. Imidazole Pyrimidine Amides as Potent, Orally Bioavailable Cyclin-Dependent Kinase Inhibitors Bioorg. Med. Chem. Lett. 2008, 18, 6486-6489
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 6486-6489
    • Jones, C.D.1    Andrews, D.M.2    Barker, A.J.3
  • 72
    • 0035821587 scopus 로고    scopus 로고
    • Structure-activity relationships of 1,4-dihydro-(1H,4H)-quinoxaline-2,3- diones as N-methyl-D-aspartate (glycine site) receptor antagonists. 1. Heterocyclic substituted 5-alkyl derivatives
    • DOI 10.1021/jm001124p
    • Fray, J. M.; Bull, D. J.; Carr, C. L.; Gautier, E. C. L.; Mowbray, C. E.; Stobie, A. Structure-Activity Relationships of 1,4-Dihydro-(1 H,4 H)-quinoxaline-2,3-diones as N -Methyl- d -aspartate (Glycine Site) Receptor Antagonists. 1. Heterocyclic Substituted 5-Alkyl Derivatives J. Med. Chem. 2001, 44, 1951-1962 (Pubitemid 32884519)
    • (2001) Journal of Medicinal Chemistry , vol.44 , Issue.12 , pp. 1951-1962
    • Fray, M.J.1    Bull, D.J.2    Carr, C.L.3    Gautier, E.C.L.4    Mowbray, C.E.5    Stobie, A.6
  • 74
    • 41149173349 scopus 로고    scopus 로고
    • Synthesis and antitubercular activity of 7-(R)- and 7-(S)-methyl-2-nitro- 6-(S)-(4-(trifluoromethoxy)benzyloxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3] oxazines, analogues of PA-824
    • DOI 10.1016/j.bmcl.2008.03.011, PII S0960894X08002758
    • Li, X.; Manjunatha, U. H.; Goodwin, M. B.; Knox, J. E.; Lipinski, C. A.; Keller, T. H.; Barry, C. E.; Dowd, C. S. Synthesis and Antitubercular Activity of 7-(R)- and 7-(S)-Methyl-2-nitro-6-(S)-(4-(trifluoromethoxy)benzyloxy)-6,7- dihydro-5 H -imidazo[2,1- b ][1,3]oxazines, Analogues of PA-824 Bioorg. Med. Chem. Lett. 2008, 18, 2256-2262 (Pubitemid 351442913)
    • (2008) Bioorganic and Medicinal Chemistry Letters , vol.18 , Issue.7 , pp. 2256-2262
    • Li, X.1    Manjunatha, U.H.2    Goodwin, M.B.3    Knox, J.E.4    Lipinski, C.A.5    Keller, T.H.6    Barry III, C.E.7    Dowd, C.S.8
  • 78
    • 18644374475 scopus 로고    scopus 로고
    • Optimization of amide-based inhibitors of soluble epoxide hydrolase with improved water solubility
    • DOI 10.1021/jm0500929
    • Kim, I.-H.; Heirtzler, F. R.; Morisseau, C.; Nishi, K.; Tsai, H.-J.; Hammock, B. D. Optimization of Amide-Based Inhibitors of Soluble Epoxide Hydrolase with Improved Water Solubility J. Med. Chem. 2005, 48, 3621-3629 (Pubitemid 40664110)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.10 , pp. 3621-3629
    • Kim, I.-H.1    Heirtzler, F.R.2    Morisseau, C.3    Nishi, K.4    Tsai, H.-J.5    Hammock, B.D.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.