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Volumn 8, Issue 1, 2011, Pages 14-25

QSAR analysis of isosteviol derivatives as α-glucosidase inhibitors with element count and other descriptors

Author keywords

glucosidase inhibitor; Glycoprotein; Hydrophobicity; Isosteviol; Nitrogen count; QSAR

Indexed keywords

ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; ISOSTEVIOL DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

EID: 78650861840     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018011793663859     Document Type: Article
Times cited : (19)

References (44)
  • 1
    • 42749087181 scopus 로고    scopus 로고
    • Binding mode analyses and pharmacophore model development for sulphonamide chalcone derivatives, a new class of α-glucosidase inhibitors
    • Kavitha, B.; Nagakumar, B.; Ki, H.P.; Keun, W.L. Binding mode analyses and pharmacophore model development for sulphonamide chalcone derivatives, a new class of α-glucosidase inhibitors. J. Mol. Graph. Model., 2008, 26, 1202-1212.
    • (2008) J. Mol. Graph. Model. , vol.26 , pp. 1202-1212
    • Kavitha, B.1    Nagakumar, B.2    Ki, H.P.3    Keun, W.L.4
  • 3
    • 0036141030 scopus 로고    scopus 로고
    • The glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step
    • Marie-Jeanne, P.O.; Rym, B.; Re Gis, G.; Marie, P.K.; Emmanuel, F. The glucosidase inhibitor 1-deoxynojirimycin blocks human immunodeficiency virus envelope glycoprotein-mediated membrane fusion at the CXCR4 binding step. Mol. Pharmacol., 2002, 61, 186-193.
    • (2002) Mol. Pharmacol. , vol.61 , pp. 186-193
    • Marie-Jeanne, P.O.1    Rym, B.2    Re Gis, G.3    Marie, P.K.4    Emmanuel, F.5
  • 4
    • 4143138851 scopus 로고    scopus 로고
    • Computer aided molecular design of novel glucosidase inhibitors for AIDS treatment
    • Silva, C.H.T.P.; Taft, C.A. Computer aided molecular design of novel glucosidase inhibitors for AIDS treatment. J. Biomol. Struct. Dyn., 2004, 22, 59-63.
    • (2004) J. Biomol. Struct. Dyn. , vol.22 , pp. 59-63
    • Silva, C.H.T.P.1    Taft, C.A.2
  • 5
    • 0038820035 scopus 로고    scopus 로고
    • Crystal structure of Thermotoga maritime α-glucosidase AglA defines a new clan of NAD+ dependent glucosidases
    • Jacinta, A.L.; Timm, M.; Wolfgang, L.; Volker, H.; Norbert, S. Crystal structure of Thermotoga maritime α-glucosidase AglA defines a new clan of NAD+ dependent glucosidases. J. Biol. Chem., 2003, 278, 19151-19158.
    • (2003) J. Biol. Chem. , vol.278 , pp. 19151-19158
    • Jacinta, A.L.1    Timm, M.2    Wolfgang, L.3    Volker, H.4    Norbert, S.5
  • 7
    • 0027959359 scopus 로고
    • Inhibition of α-glucosidase i of the glycoproteinprocessing enzymes by 6-0-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells
    • Debra, T.; Mohinder, S.K.; Tara, M.B.; Gordon, B.; Prasad, S.S.; Stanley, T. Inhibition of α-glucosidase I of the glycoproteinprocessing enzymes by 6-0-butanoyl castanospermine (MDL 28,574) and its consequences in human immunodeficiency virus-infected T cells. Antimicrob. Agents Chemother., 1994, 38, 1780-1787.
    • (1994) Antimicrob. Agents Chemother. , vol.38 , pp. 1780-1787
    • Debra, T.1    Mohinder, S.K.2    Tara, M.B.3    Gordon, B.4    Prasad, S.S.5    Stanley, T.6
  • 8
    • 22144477181 scopus 로고    scopus 로고
    • Homology modeling and molecular interaction field studies of α-glucosidase as a guide to structure based drug design of novel proposed anti-HIV inhibitors
    • Tomich, C.H.; da Silva, P.; Ivone, C.; Taft, C.A. Homology modeling and molecular interaction field studies of α-glucosidase as a guide to structure based drug design of novel proposed anti-HIV inhibitors. J. Comput. Aided Drug Des., 2005, 19, 83-92.
    • (2005) J. Comput. Aided Drug Des. , vol.19 , pp. 83-92
    • Tomich, C.H.1    Da Silva, P.2    Ivone, C.3    Taft, C.A.4
  • 9
    • 48449092937 scopus 로고    scopus 로고
    • Synthesis inhibitory activities and QSAR study of xanthone derivatives as α-glucosidase inhibitors
    • Yan, L.; Zhuofeng, K.; Jianfang, C.; Wen-Hua, C.; Lin, M.; Bo, W. Synthesis, inhibitory activities and QSAR study of xanthone derivatives as α-glucosidase inhibitors. Bioorg. Med. Chem., 2008, 16, 7185-7192.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7185-7192
    • Yan, L.1    Zhuofeng, K.2    Jianfang, C.3    Wen-Hua, C.4    Lin, M.5    Bo, W.6
  • 11
    • 0026633949 scopus 로고
    • Renal excretion of stevioside in rats
    • Melis, M.S. Renal excretion of stevioside in rats. J. Nat. Prod., 1992, 55, 688-690.
    • (1992) J. Nat. Prod. , vol.55 , pp. 688-690
    • Melis, M.S.1
  • 12
    • 39049123050 scopus 로고    scopus 로고
    • Microbial transformation of isosteviol and bioactivities against the glucocorticoid/androgen response elements
    • Chang, S.F.; Yang, L.M.; Lo, C.H.; Liaw, J.H.; Wang, L.H.; Li, S.J. Microbial transformation of isosteviol and bioactivities against the glucocorticoid/androgen response elements. J. Nat. Prod., 2008, 71, 87-92.
    • (2008) J. Nat. Prod. , vol.71 , pp. 87-92
    • Chang, S.F.1    Yang, L.M.2    Lo, C.H.3    Liaw, J.H.4    Wang, L.H.5    Li, S.J.6
  • 13
    • 0043053467 scopus 로고    scopus 로고
    • Inhibitory effect of stevioside on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two stage carcinogenesis in mouse skin
    • Yasukawa, K.; Kitanika, S.; Seo, S. Inhibitory effect of stevioside on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two stage carcinogenesis in mouse skin. Biol. Pharm. Bull., 2002, 25, 1488-1490.
    • (2002) Biol. Pharm. Bull. , vol.25 , pp. 1488-1490
    • Yasukawa, K.1    Kitanika, S.2    Seo, S.3
  • 14
    • 78650880393 scopus 로고    scopus 로고
    • Chem BioOffice 2008, CambridgeSoft Corp, UK, 2008
    • Chem BioOffice 2008, CambridgeSoft Corp, UK, 2008.
  • 17
    • 8844285333 scopus 로고    scopus 로고
    • QSAR modelling of HIV-1 reverse transcriptase inhibition by benzoxazinones using a combination of P-VSA and pharmacophore feature descriptors
    • Balaji, S.; Karthikeyan, C.; Moorthy, N.S.H.N.; Trivedi, P. QSAR modelling of HIV-1 reverse transcriptase inhibition by benzoxazinones using a combination of P-VSA and pharmacophore feature descriptors. Bioorg. Med. Chem. Lett., 2004, 14, 6089-6094.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 6089-6094
    • Balaji, S.1    Karthikeyan, C.2    Moorthy, N.S.H.N.3    Trivedi, P.4
  • 19
    • 58949091558 scopus 로고    scopus 로고
    • QSAR study of substituted 2-pyridinyl quanidine as selective uro kinase-type plasminogen activator (uPA) inhibitors
    • Karthikeyan, C.; Moorthy, N.S.H.N.; Trivedi, P. QSAR study of substituted 2-pyridinyl quanidine as selective uro kinase-type plasminogen activator (uPA) inhibitors. J. Enzyme Inhib. Med. Chem., 2009, 24, 6-13.
    • (2009) J. Enzyme Inhib. Med. Chem , vol.24 , pp. 6-13
    • Karthikeyan, C.1    Moorthy, N.S.H.N.2    Trivedi, P.3
  • 20
    • 0343831900 scopus 로고    scopus 로고
    • Quantitative structure activity relationship (QSAR) study of new fluorovinyloxyacetamides
    • Cho, D.H.; Lee, S.K.; Kim, B.T.; No, K.T. Quantitative structure activity relationship (QSAR) study of new fluorovinyloxyacetamides. Bull. Korean Chem. Soc., 2001, 22, 388-394.
    • (2001) Bull. Korean Chem. Soc , vol.22 , pp. 388-394
    • Cho, D.H.1    Lee, S.K.2    Kim, B.T.3    No, K.T.4
  • 21
    • 30244459245 scopus 로고
    • Testing for serial correlation in least squares regression. II
    • Durbin, J.; Watson, G.S. Testing for serial correlation in least squares regression. II. Biometrika, 1951, 38, 159-178.
    • (1951) Biometrika , vol.38 , pp. 159-178
    • Durbin, J.1    Watson, G.S.2
  • 22
    • 34250628103 scopus 로고    scopus 로고
    • Principle of QSAR model validation: Internal and external
    • Gramatica, P. Principle of QSAR model validation: internal and external. QSAR Comb. Sci., 2007, 26, 694-701.
    • (2007) QSAR Comb. Sci. , vol.26 , pp. 694-701
    • Gramatica, P.1
  • 23
    • 0038724207 scopus 로고    scopus 로고
    • The importance of earnest, validation is the absolute essential application and interpretation of QSPR models
    • Tropsha, A.; Gramatica, P.; Gombar, V.K. The importance of earnest, validation is the absolute essential application and interpretation of QSPR models. QSAR Comb. Sci., 2003, 22, 69-77.
    • (2003) QSAR Comb. Sci. , vol.22 , pp. 69-77
    • Tropsha, A.1    Gramatica, P.2    Gombar, V.K.3
  • 24
    • 0043132440 scopus 로고    scopus 로고
    • Methods for reliability and uncertainty assessment and for applicability evaluation of classification and regression based QSARs
    • Erikkson, L.; Jaworsha, J.; Worth, A.P.; Mark, T.D.C.; Robert, M.M.; Gramatica, P. Methods for reliability and uncertainty assessment and for applicability evaluation of classification and regression based QSARs. Environ. Health Perspect., 2003, 111, 1361-1375.
    • (2003) Environ. Health Perspect. , vol.111 , pp. 1361-1375
    • Erikkson, L.1    Jaworsha, J.2    Worth, A.P.3    Mark, T.D.C.4    Robert, M.M.5    Gramatica, P.6
  • 26
    • 84918743166 scopus 로고
    • Dennis. Influential observation in linear regression
    • Cook, R.; Dennis. Influential observation in linear regression. J. Am. Stat. Assoc. 1979, 74, 169-174.
    • (1979) J. Am. Stat. Assoc. , vol.74 , pp. 169-174
    • Cook, R.1
  • 27
    • 78650854138 scopus 로고
    • Linear models for continuous data
    • Rodriquez, G. Linear models for continuous data, Chapter 2. 1993-2000, pp. 49-58 (http://data.princeton.edu/wws509/notes).
    • (1993) Chapter 2 , pp. 49-58
    • Rodriquez, G.1
  • 29
    • 15944401769 scopus 로고    scopus 로고
    • QSAR analyses of conformationally restricted 1,5-diaryl pyrazoles as selective COX-2 inhibitors: Application of connection table representation of ligands
    • Prasanna, S.; Manivannan, E.; Chaturvedi, S.C. QSAR analyses of conformationally restricted 1,5-diaryl pyrazoles as selective COX-2 inhibitors: application of connection table representation of ligands. Bioorg. Med. Chem. Lett., 2005, 15, 2097-2102.
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 2097-2102
    • Prasanna, S.1    Manivannan, E.2    Chaturvedi, S.C.3
  • 30
    • 0030040323 scopus 로고    scopus 로고
    • Reduced surface: An efficient way to compute molecular surfaces
    • Sanner, M.F.; Olson, A.J.; Spehner, J.C. Reduced surface: an efficient way to compute molecular surfaces. Biopolymer, 1996, 38, 305-320.
    • (1996) Biopolymer , vol.38 , pp. 305-320
    • Sanner, M.F.1    Olson, A.J.2    Spehner, J.C.3
  • 31
    • 0037498039 scopus 로고    scopus 로고
    • ADME evaluation in drug discovery. 2. Prediction of partition coefficient by atom-additive approach based on atom-weighted solvent accessible surface areas
    • Hou, T.J.; Xu, X.J. ADME evaluation in drug discovery. 2. Prediction of partition coefficient by atom-additive approach based on atom-weighted solvent accessible surface areas. J. Chem. Inf. Comput. Sci., 2003, 43, 1058-1067.
    • (2003) J. Chem. Inf. Comput. Sci. , vol.43 , pp. 1058-1067
    • Hou, T.J.1    Xu, X.J.2
  • 32
    • 0022649317 scopus 로고
    • A new approach of structure activity relationships: The 'potential of molecular lipophilicity
    • Audry, E.; Dubost, J.P.; Colleter, J.C.; Dallet, P. A new approach of structure activity relationships: The 'potential of molecular lipophilicity. Eur. J. Med. Chem., 1986, 21, 71-72.
    • (1986) Eur. J. Med. Chem. , vol.21 , pp. 71-72
    • Audry, E.1    Dubost, J.P.2    Colleter, J.C.3    Dallet, P.4
  • 33
    • 0015755443 scopus 로고
    • Statistical analysis of a series of partition coefficients with special reference to the predictability of folding of drug molecules. Introduction of hydrophobic fragmental constants (f-values)
    • Nys, G.G.; Rekker, R.F. Statistical analysis of a series of partition coefficients with special reference to the predictability of folding of drug molecules. Introduction of hydrophobic fragmental constants (f-values). Chim. Therap., 1973, 8, 521-535.
    • (1973) Chim. Therap. , vol.8 , pp. 521-535
    • Nys, G.G.1    Rekker, R.F.2
  • 34
    • 0016350063 scopus 로고
    • The concept of hydrophobic fragmental constants (f-values) II. Extension to its applicability to the calculation of lipophiIicities of aromatic and heteroaromatic structures
    • Nys, G.G.; Rekker, R.F. The concept of hydrophobic fragmental constants (f-values) II. Extension to its applicability to the calculation of lipophiIicities of aromatic and heteroaromatic structures. Eur. J. Med. Chem-Chim. Therap., 1974, 9, 361-375.
    • (1974) Eur. J. Med. Chem-Chim. Therap. , vol.9 , pp. 361-375
    • Nys, G.G.1    Rekker, R.F.2
  • 35
    • 0035055492 scopus 로고    scopus 로고
    • Substructure and whole molecule approaches for calculating log P
    • Mannhold, R.; van de Waterbeemed. Substructure and whole molecule approaches for calculating log P. J. Comput. Aided Mol. Des., 2001, 15, 337-354.
    • (2001) J. Comput. Aided Mol. Des. , vol.15 , pp. 337-354
    • Mannhold, R.1    Van De, W.2
  • 36
    • 0026292147 scopus 로고
    • HINT - A new method of empirical hydrophobic field calculation for CoMFA
    • Kellogg, G.E.; Semus, S.F.; Abraham, D.J.; HINT - A new method of empirical hydrophobic field calculation for CoMFA. J. Comput. Aided Mol. Des., 1991, 5, 545-552.
    • (1991) J. Comput. Aided Mol. Des. , vol.5 , pp. 545-552
    • Kellogg, G.E.1    Semus, S.F.2    Abraham, D.J.3
  • 37
    • 0001126839 scopus 로고
    • New tools for modeling and understanding hydrophobicity and hydrophobic interactions
    • Kellogg, G.E.; Joshi, G.S.; Abraham, D.J. New tools for modeling and understanding hydrophobicity and hydrophobic interactions. Med. Chem. Res., 1992, 1, 444-453.
    • (1992) Med. Chem. Res. , vol.1 , pp. 444-453
    • Kellogg, G.E.1    Joshi, G.S.2    Abraham, D.J.3
  • 38
    • 0027080363 scopus 로고
    • KEY LOCK, and LOCKSMITH. Complementary hydrophobicity map predictions of drug structure from a known receptor/receptor structure from known drugs
    • Kellogg, G.E.; Abraham, D.J. KEY, LOCK, and LOCKSMITH. Complementary hydrophobicity map predictions of drug structure from a known receptor/receptor structure from known drugs. J. Mol. Graphics, 1992, 10, 212-217.
    • (1992) J. Mol. Graphics , vol.10 , pp. 212-217
    • Kellogg, G.E.1    Abraham, D.J.2
  • 39
    • 0028455325 scopus 로고
    • Evaluating docked complexes with the HINT exponential function and empirical atomic hydrophobicities
    • Meng, E.C.; Kuntz, I.D.; Abraham, D.J.; Kellogg, G.E. Evaluating docked complexes with the HINT exponential function and empirical atomic hydrophobicities. J. Comput. Aided Mol. Des., 1994, 8, 299-306.
    • (1994) J. Comput. Aided Mol. Des. , vol.8 , pp. 299-306
    • Meng, E.C.1    Kuntz, I.D.2    Abraham, D.J.3    Kellogg, G.E.4
  • 40
    • 0343517556 scopus 로고    scopus 로고
    • Hydrophobicity: Is LogPo/w more than the sum of its parts?
    • Kellogg, G.E.; Abraham, D.J. Hydrophobicity: Is LogPo/w more than the sum of its parts?. Eur. J. Med. Chem., 2000, 35, 651-661.
    • (2000) Eur. J. Med. Chem. , vol.35 , pp. 651-661
    • Kellogg, G.E.1    Abraham, D.J.2
  • 41
    • 0032976819 scopus 로고    scopus 로고
    • Development of empirical biomolecular interaction models that incorporate hydrophobicity and hydropathy. The HINT paradigm
    • Kellogg, G.E.; Abraham, D.J. Development of empirical biomolecular interaction models that incorporate hydrophobicity and hydropathy. The HINT paradigm. Analysis, 1999, 27, 19-22.
    • (1999) Analysis , vol.27 , pp. 19-22
    • Kellogg, G.E.1    Abraham, D.J.2
  • 42
    • 78650014134 scopus 로고
    • Testing for serial correlation in least squares regression.1
    • Durbin, J.; Watson, G.S. Testing for serial correlation in least squares regression.1. Biometrika, 1950, 37, 409-428.
    • (1950) Biometrika , vol.37 , pp. 409-428
    • Durbin, J.1    Watson, G.S.2
  • 43
    • 42149090634 scopus 로고    scopus 로고
    • Structure-activity landscape index: Identifying and quantifying activity cliffs
    • Guha, R.; Van Drie, J.H. Structure-activity landscape index: Identifying and quantifying activity cliffs. J. Chem. Inf. Model., 2008, 48, 646-658.
    • (2008) J. Chem. Inf. Model. , vol.48 , pp. 646-658
    • Guha, R.1    Van Drie, J.H.2


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