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Volumn 42, Issue 26, 1999, Pages 5348-5358

Comparative molecular field analysis of fungal squalene epoxidase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZYLAMINE DERIVATIVE; OXYGENASE INHIBITOR; SQUALENE MONOOXYGENASE; TERBINAFINE;

EID: 0033619988     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9806852     Document Type: Article
Times cited : (37)

References (43)
  • 2
    • 0023182209 scopus 로고
    • Allylamine derivatives - A new class of active substances in antifungal chemotherapy
    • Stutz, A. Allylamine Derivatives - A New Class of Active Substances in Antifungal Chemotherapy. Angew. Chem., Int. Ed. Engl. 1987, 26, 320-328.
    • (1987) Angew. Chem., Int. Ed. Engl. , vol.26 , pp. 320-328
    • Stutz, A.1
  • 3
    • 0025022276 scopus 로고
    • Inhibition of squalene epoxidase and sterol side-chain methylation by allylamines
    • Ryder, N. S. Inhibition of Squalene Epoxidase and Sterol Side-Chain Methylation by Allylamines. Biochem. Soc. Trans. 1980, 18, 45-46.
    • (1980) Biochem. Soc. Trans. , vol.18 , pp. 45-46
    • Ryder, N.S.1
  • 4
    • 0022384997 scopus 로고
    • Inhibition of squalene epoxidase by allylamine antimycotic compounds - A comparative study of fungal and mammalian enzymes
    • Ryder, N. S.; Dupont, M. Inhibition of Squalene Epoxidase by Allylamine Antimycotic Compounds - A Comparative Study of Fungal and Mammalian Enzymes. Biochem. J. 1985, 230, 765-770.
    • (1985) Biochem. J. , vol.230 , pp. 765-770
    • Ryder, N.S.1    Dupont, M.2
  • 5
    • 0020360216 scopus 로고
    • Squalene and ergosterol biosynthesis in fungi treated with naftifine, a new antimycotic agent
    • Paltauf, F.; Daum, G.; Zuder, G.; Hogenauer, G.; Schulz, G.; Seidl, G. Squalene and Ergosterol Biosynthesis In Fungi Treated with Naftifine, A New Antimycotic Agent. Biochim. Biophys. Acta 1982, 712, 268-273.
    • (1982) Biochim. Biophys. Acta , vol.712 , pp. 268-273
    • Paltauf, F.1    Daum, G.2    Zuder, G.3    Hogenauer, G.4    Schulz, G.5    Seidl, G.6
  • 6
    • 0026031236 scopus 로고
    • Synthesis and structure-activity relationships of Benzo[b]thienylallylamine antimycotics
    • Nussbaumer, P.; Petranyi, G.; Stutz, A. Synthesis and Structure-Activity Relationships of Benzo[b]thienylallylamine Antimycotics. J. Med. Chem. 1991, 34, 65-73.
    • (1991) J. Med. Chem. , vol.34 , pp. 65-73
    • Nussbaumer, P.1    Petranyi, G.2    Stutz, A.3
  • 7
    • 0027282428 scopus 로고
    • Synthesis and structure-activity relationships of phenyl-substituted benzylamine antimycotics: A novel benzylbenzylamine antifungal agent for systemic treatment
    • Nussbaumer, P.; Dorfstatter, G.; Grassberger, M. A.; Leitner, I.; Meingasser, J. G.; Thirring, K.; Stutz, A. Synthesis and Structure-Activity Relationships of Phenyl-substituted Benzylamine Antimycotics: A Novel Benzylbenzylamine Antifungal Agent for Systemic Treatment. J. Med. Chem. 1993, 36, 2115-2120.
    • (1993) J. Med. Chem. , vol.36 , pp. 2115-2120
    • Nussbaumer, P.1    Dorfstatter, G.2    Grassberger, M.A.3    Leitner, I.4    Meingasser, J.G.5    Thirring, K.6    Stutz, A.7
  • 8
    • 0027426864 scopus 로고
    • Synthesis and structure-activity relationships of naphthalene-substituted derivatives of the allylamine antimycotic terbinafine
    • Nussbaumer, P.; Dorfstatter, G.; Leitner, I.; Mraz, K.; Vylpel, H.; Stutz, A. Synthesis and Structure-Activity Relationships of Naphthalene-Substituted Derivatives of the Allylamine Antimycotic Terbinafine. J. Med. Chem. 1993, 36, 2810-2816.
    • (1993) J. Med. Chem. , vol.36 , pp. 2810-2816
    • Nussbaumer, P.1    Dorfstatter, G.2    Leitner, I.3    Mraz, K.4    Vylpel, H.5    Stutz, A.6
  • 9
    • 0028326187 scopus 로고
    • Synthesis of structure-activity relationships of the novel homopropargylamine antimycotics
    • Nussbaumer, P.; Leitner, I.; Stutz, A. Synthesis of Structure-Activity Relationships of the Novel Homopropargylamine Antimycotics. J. Med. Chem. 1994, 37, 610-615.
    • (1994) J. Med. Chem. , vol.37 , pp. 610-615
    • Nussbaumer, P.1    Leitner, I.2    Stutz, A.3
  • 10
    • 0029000697 scopus 로고
    • Synthesis and structure-activity relationships of side-chain substituted analogues of the allylamine antimycotic terbinafine lacking the central amino function
    • Nussbaumer, P.; Leitner, I.; Mraz, K.; Stutz, A. Synthesis and Structure-Activity Relationships of Side-Chain Substituted Analogues of the Allylamine Antimycotic Terbinafine Lacking the Central Amino Function. J. Med. Chem. 1995, 38, 1831-1836.
    • (1995) J. Med. Chem. , vol.38 , pp. 1831-1836
    • Nussbaumer, P.1    Leitner, I.2    Mraz, K.3    Stutz, A.4
  • 11
    • 0023751431 scopus 로고
    • Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer, R. D.; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 12
    • 0027397374 scopus 로고
    • On the prediction of binding properties of drug molecules by comparative molecular field analysis
    • Klebe, G.; Abraham, U. On the Prediction of Binding Properties of Drug Molecules by Comparative Molecular Field Analysis. J. Med. Chem. 1993, 36, 70-80.
    • (1993) J. Med. Chem. , vol.36 , pp. 70-80
    • Klebe, G.1    Abraham, U.2
  • 13
    • 0027308233 scopus 로고
    • Three-dimensional quantitative structure-activity relationship of angiotensin converting enzyme and thermolysin inhibitors. II. A comparison of CoMFA models incorporating molecular orbital fields and desolvation free energies based on active-analogue and complementary-receptor-field alignment rules
    • Waller, C. L.; Marshall, G. R. Three-Dimensional Quantitative Structure-Activity Relationship of Angiotensin Converting Enzyme and Thermolysin Inhibitors. II. A Comparison of CoMFA Models Incorporating Molecular Orbital Fields and Desolvation Free Energies Based on Active-Analogue and Complementary-Receptor-Field Alignment Rules. J. Med. Chem. 1993, 36, 2390-2403.
    • (1993) J. Med. Chem. , vol.36 , pp. 2390-2403
    • Waller, C.L.1    Marshall, G.R.2
  • 14
    • 0027183015 scopus 로고
    • 3D-QSAR of angiotensin-converting enzyme and thermolysin inhibitors: A comparison of CoMFA models based on deduced and experimentally determined active site geometries
    • Depriest, S. A.; Mayer, D.; Naylor, C. B.; Marshall, G. R. 3D-QSAR of Angiotensin-Converting Enzyme and Thermolysin inhibitors: A Comparison of CoMFA Models Based on Deduced and Experimentally Determined Active Site Geometries. J. Am. Chem. Soc. 1993, 115, 5372-5384.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5372-5384
    • Depriest, S.A.1    Mayer, D.2    Naylor, C.B.3    Marshall, G.R.4
  • 15
    • 0027762073 scopus 로고
    • Three-dimensional QSAR of human immunodeficiency virus (I) protease inhibitors. 1. A CoMFA study employing experimentally determined alignment rules
    • Waller, C. L.; Oprea, T. I.; Gliotti, A.; Marshall, G. R. Three-Dimensional QSAR of Human Immunodeficiency Virus (I) Protease Inhibitors. 1. A CoMFA Study Employing Experimentally Determined Alignment Rules. J. Med. Chem. 1993, 36, 4152-4160.
    • (1993) J. Med. Chem. , vol.36 , pp. 4152-4160
    • Waller, C.L.1    Oprea, T.I.2    Gliotti, A.3    Marshall, G.R.4
  • 16
    • 0028924311 scopus 로고
    • Three-dimensional quantitative structure activity relationship (QSAR) of HIV integrase inhibitors: A comparative molecular field analysis study
    • Raghavan, K.; Buolawmini, J. K.; Fesen, M.; Pommier, Y.; Kohn, K. W.; Weinstein, J. N. Three-Dimensional Quantitative Structure Activity Relationship (QSAR) of HIV Integrase Inhibitors: A Comparative Molecular Field Analysis Study. J. Med. Chem. 1995, 38, 890-897.
    • (1995) J. Med. Chem. , vol.38 , pp. 890-897
    • Raghavan, K.1    Buolawmini, J.K.2    Fesen, M.3    Pommier, Y.4    Kohn, K.W.5    Weinstein, J.N.6
  • 17
    • 0030054277 scopus 로고    scopus 로고
    • A comparative molecular field analysis study of N-Benzylpiperidines as acetylcholinesterase inhibitors
    • Tong, W.; Collantes, E. R.; Chen, Y.; Welsh, W. J. A Comparative Molecular Field Analysis Study of N-Benzylpiperidines as Acetylcholinesterase Inhibitors. J. Med. Chem. 1996, 39, 380-387.
    • (1996) J. Med. Chem. , vol.39 , pp. 380-387
    • Tong, W.1    Collantes, E.R.2    Chen, Y.3    Welsh, W.J.4
  • 18
    • 0000261607 scopus 로고    scopus 로고
    • Structure-based alignment and comparative molecular field analysis of acetylcholinesterase inhibitors
    • Cho, S. J.; Garsia, M. L. S.; Bier, J.; Tropsha, A. Structure-Based Alignment and Comparative Molecular Field Analysis of Acetylcholinesterase Inhibitors. J. Med. Chem. 1996, 39, 5064-5071.
    • (1996) J. Med. Chem. , vol.39 , pp. 5064-5071
    • Cho, S.J.1    Garsia, M.L.S.2    Bier, J.3    Tropsha, A.4
  • 19
    • 0030892498 scopus 로고    scopus 로고
    • Reliability of comparative molecular field analysis models: Effects of data scaling and variable selection using a set of human synovial fluid phospholipase A2 inhibitors
    • Ortiz, A. R.; Pastor, M.; Palomer, A.; Cruciani, G.; Gago, F.; Wade, R. C. Reliability of Comparative Molecular Field Analysis Models: Effects of Data Scaling and Variable Selection Using a Set of Human Synovial Fluid Phospholipase A2 Inhibitors. J. Med. Chem. 1997, 40, 1136-1148.
    • (1997) J. Med. Chem. , vol.40 , pp. 1136-1148
    • Ortiz, A.R.1    Pastor, M.2    Palomer, A.3    Cruciani, G.4    Gago, F.5    Wade, R.C.6
  • 20
    • 0030636777 scopus 로고    scopus 로고
    • Comparative molecular field analysis and molecular modeling studies of 20-(S)-camptothecin analogues as inhibitors of DNA topoisomerase i and anticancer/antitumor agents
    • Carrigan, S. W.; Fox, P. C.; Wall, M. E.; Wani, M. C.; Bowen, P. J. Comparative Molecular Field Analysis and Molecular Modeling Studies of 20-(S)-Camptothecin Analogues as Inhibitors of DNA topoisomerase I and Anticancer/antitumor Agents. J. Comput.-Aided Mol. Des. 1997, 11, 71-78.
    • (1997) J. Comput.-Aided Mol. Des. , vol.11 , pp. 71-78
    • Carrigan, S.W.1    Fox, P.C.2    Wall, M.E.3    Wani, M.C.4    Bowen, P.J.5
  • 21
    • 0032972812 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure activity relationship of interleukin-1β converting enzyme inhibitors: A comparative molecular field analysis study
    • Kulkarni, S. S.; Kulkarni, V. M. Three-Dimensional Quantitative Structure Activity Relationship of Interleukin-1β Converting Enzyme Inhibitors: A Comparative Molecular Field Analysis Study. J. Med. Chem. 1999, 42, 373-380.
    • (1999) J. Med. Chem. , vol.42 , pp. 373-380
    • Kulkarni, S.S.1    Kulkarni, V.M.2
  • 22
    • 0027032097 scopus 로고
    • A comparison of progestin and androgen binding using the CoMFA technique
    • Loghney, D. A.; Schwender, C. F. A Comparison of Progestin and Androgen Binding using the CoMFA technique. J. Comput.-Aided Mol. Des. 1992, 6, 569-581.
    • (1992) J. Comput.-aided Mol. Des. , vol.6 , pp. 569-581
    • Loghney, D.A.1    Schwender, C.F.2
  • 24
    • 0029012712 scopus 로고
    • Three-dimensional quantitative structure activity relationship of sulfonamide endothelin inhibitors
    • Krystek, S. R.; Hunt, J. T.; Stein, P. D.; Stouch, T. R. Three-Dimensional Quantitative Structure Activity Relationship of Sulfonamide Endothelin Inhibitors. J. Med. Chem. 1995, 38, 659-668.
    • (1995) J. Med. Chem. , vol.38 , pp. 659-668
    • Krystek, S.R.1    Hunt, J.T.2    Stein, P.D.3    Stouch, T.R.4
  • 25
    • 0031052115 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relaionship of melatonin receptor ligands: A comparative molecular field analysis study
    • Sicsic, S.; Serraz, I.; Andrieux, J.; Bremont, B.; Allanmant, M. M.; Poncet, A.; Shen, S.; Langlois, M. Three-Dimensional Quantitative Structure-Activity Relaionship of Melatonin Receptor Ligands: A Comparative Molecular Field Analysis Study. J. Med. Chem. 1997, 40, 739-748.
    • (1997) J. Med. Chem. , vol.40 , pp. 739-748
    • Sicsic, S.1    Serraz, I.2    Andrieux, J.3    Bremont, B.4    Allanmant, M.M.5    Poncet, A.6    Shen, S.7    Langlois, M.8
  • 26
    • 15444338833 scopus 로고    scopus 로고
    • Flavonoid derivatives as adenosine receptor antagonists: A comparison of the hypothetical receptor binding site based on a comparative molecular field analysis model
    • Moro, S.; Rhee, A. M.; Sanders, L. H.; Jacobson, K. A. Flavonoid Derivatives as Adenosine Receptor Antagonists: A Comparison of the Hypothetical Receptor Binding Site Based on a Comparative Molecular Field Analysis Model. J. Med. Chem. 1998, 41, 46-52.
    • (1998) J. Med. Chem. , vol.41 , pp. 46-52
    • Moro, S.1    Rhee, A.M.2    Sanders, L.H.3    Jacobson, K.A.4
  • 27
    • 0031012989 scopus 로고    scopus 로고
    • Diltiazem-like calcium entry blockers. A hypothesis of the receptor-binding site based on a comparative molecular field analysis model
    • Corelli, F.; Manetti, F.; Tafi, A.; Campiani, G.; Nacci, V.; Botta, M. Diltiazem-like Calcium Entry Blockers. A Hypothesis of the Receptor-Binding Site Based on a Comparative Molecular Field Analysis Model. J. Med. Chem. 1997, 40, 125-131.
    • (1997) J. Med. Chem. , vol.40 , pp. 125-131
    • Corelli, F.1    Manetti, F.2    Tafi, A.3    Campiani, G.4    Nacci, V.5    Botta, M.6
  • 29
    • 0026638019 scopus 로고
    • Comparative molecular field analysis of anticoccidial triazines
    • McFarland, J. W. Comparative Molecular Field Analysis of Anticoccidial Triazines. J. Med. Chem. 1992, 35, 2543-2550.
    • (1992) J. Med. Chem. , vol.35 , pp. 2543-2550
    • McFarland, J.W.1
  • 32
    • 0026572175 scopus 로고
    • CoMFA analysis of the interaction of antipicornavirus compounds in the binding pocket of human rhinovirus-14
    • Diana, G. D.; Kowalczyk, P.; Treasurywala, A. M.; Oglesby, R. C.; Pevear, D. C.; Dutko, F. J. CoMFA Analysis of the Interaction of Antipicornavirus Compounds in the Binding Pocket of Human Rhinovirus-14. J. Med. Chem. 1992, 35, 1002-1008.
    • (1992) J. Med. Chem. , vol.35 , pp. 1002-1008
    • Diana, G.D.1    Kowalczyk, P.2    Treasurywala, A.M.3    Oglesby, R.C.4    Pevear, D.C.5    Dutko, F.J.6
  • 34
    • 0032576701 scopus 로고    scopus 로고
    • Quantitative analysis of the structural requirements for blockade of the N-Methyl D-aspartate receptor at the phencyclidine binding site
    • Kroemer, R. T.; Koutsilieri, E.; Hecht, P.; Liedl, K. R.; Riederer, P.; Kornhuber, J. Quantitative Analysis of the Structural Requirements for Blockade of the N-Methyl D-aspartate Receptor at the Phencyclidine Binding Site. J. Med. Chem. 1998, 41, 393-400.
    • (1998) J. Med. Chem. , vol.41 , pp. 393-400
    • Kroemer, R.T.1    Koutsilieri, E.2    Hecht, P.3    Liedl, K.R.4    Riederer, P.5    Kornhuber, J.6
  • 35
    • 0026774557 scopus 로고
    • A combined use of quantum chemical parameters, hydrophobic and geometrical descriptors to establish QSARs of allylamine antimycotics
    • Hecht, P.; Vylpel, H.; Nussbaumer, P.; Berner, H. A Combined Use of Quantum Chemical Parameters, Hydrophobic and Geometrical Descriptors to Establish QSARs of Allylamine Antimycotics. Quant. Struct.-Act. Relat. 1992, 11, 339-347.
    • (1992) Quant. Struct.-Act. Relat. , vol.11 , pp. 339-347
    • Hecht, P.1    Vylpel, H.2    Nussbaumer, P.3    Berner, H.4
  • 36
    • 0342867038 scopus 로고    scopus 로고
    • SYBYL 6.22 is available from Tripos Associates Inc., Hanley Road, St. Louis, MO 63144-2913
    • SYBYL 6.22 is available from Tripos Associates Inc., Hanley Road, St. Louis, MO 63144-2913.
  • 37
    • 84988115618 scopus 로고
    • Validation of the general-purpose tripos 5.2 force field
    • Clark, M.; Cramer, R. D., III; Van Opdenbosh, N. Validation of the General-Purpose Tripos 5.2 force field. J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clark, M.1    Cramer R.D. III2    Van Opdenbosh, N.3
  • 39
    • 24444468650 scopus 로고
    • Ground state of molecules: 38 the MNDO method. Approximations and parameters
    • Dewar, M. J. S.; Thiel, W. Ground State of Molecules: 38 The MNDO Method. Approximations and Parameters. J. Am. Chem. Soc. 1977, 99, 4899-4915.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4899-4915
    • Dewar, M.J.S.1    Thiel, W.2
  • 40
    • 0342867037 scopus 로고    scopus 로고
    • MOPAC 6.00 is available from Quantum Chemical Program Exchange, Indiana University, no. 455
    • MOPAC 6.00 is available from Quantum Chemical Program Exchange, Indiana University, no. 455.
  • 41
    • 0342867036 scopus 로고    scopus 로고
    • Cerius2 3.5 is available from Molecular Simulation Inc., Scranton Road, San Diego, CA
    • Cerius2 3.5 is available from Molecular Simulation Inc., Scranton Road, San Diego, CA.
  • 42
    • 0342432568 scopus 로고    scopus 로고
    • ClogP version 1.0.0; Biobyte Corp., 201 West 4th Street, Suite 204, Claremount, CA 91711
    • ClogP version 1.0.0; Biobyte Corp., 201 West 4th Street, Suite 204, Claremount, CA 91711.
  • 43
    • 0031059044 scopus 로고    scopus 로고
    • Antiulcer agents 6. Analysis of the in vitro biochemical and in vivo gastric antisecretory activity of substituted imidazo[1,2-α]pyridines and related analogues using comparative molecular field analysis and hypothetical active site lattice methodologies
    • Kaminski, J. J.; Doweyko, A. M. Antiulcer Agents 6. Analysis of the in vitro Biochemical and in vivo Gastric Antisecretory Activity of Substituted Imidazo[1,2-α]pyridines and Related Analogues Using Comparative Molecular Field Analysis and Hypothetical Active Site Lattice Methodologies. J. Med. Chem. 1997, 40, 427-436.
    • (1997) J. Med. Chem. , vol.40 , pp. 427-436
    • Kaminski, J.J.1    Doweyko, A.M.2


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