Comparison of Benzodiazepine-Like Compounds Using Topological Analysis and Genetic Algorithms

References

• Allen , F. H. , Kennard , O. and Taylor , R. 1983 . Systematic Analysis of Structural Data as a Research Technique in Organic Chemistry . Acć. Chem. Res. , 16 : 146 – 153 .
   Web of Science ®Google Scholar
• Anholt , R. R. H. , Pedersen , P. L. , De Souza , E. B. and Snyder , S. H. 1986 . The Peripheral-Type Benzodiazepine Receptor - Localization to the Mitochondrial Outer Membrane . J. Biol. Chem. , 261 : 576 – 583 .
   PubMed Web of Science ®Google Scholar
• Bader , R. F. W. 1990 . Atoms in Molecules – A Quantum Theory. , 438 Oxford : Oxford Science Publications, Clarendon Press .
   Google Scholar
• Bernassau , J. M. , Reversat , J. L. , Ferrara , P. , Caput , D. and Lefur , G. 1993 . A 3D Model of the Peripheral Benzodiazepine Receptor and its Implication in Intra Mitochondrial Cholesterol Transport . J. Mol. Graphics , 1 : 235 – 244 .
   Google Scholar
• Bourguignon , J.-J. , Chambon , J. P. and Wermuth , C. G. Triazolo [4,3-b]-pyridazines, procédé pour leur préparation et compositions pharmaceutiques les contenant . Eur. Pat, EP 156 734 . 1985 .
   Google Scholar
• Bourguignon , J.-J. , Wermuth , C. G. , Renaud de la Faverie , J. F. , Thollon , C. and Lombet , A. Preparation of Imidazo[1,2-c]quinazolines as Smooth Muscle Relaxants . Eur. Pat. Appl., EP446 141, 11th Sept. . 1991, 1991 . Chem. Abstr., 116, 21068g.
   Google Scholar
• Bourguignon , J.-J. 1993 . “ Endogenous and Synthetic Ligands of Mitochondrial Benzodiazepine Receptors: Structure-Affinity Relationships ” . In Peripheral Benzodiazepine Receptors , Edited by: Giesen-Crouse , E. 59 – 85 . London : Academic Press .
   Google Scholar
• Braestrup , C. and Squires , R. F. 1977 . Specific Benzodiazepine Receptors in Rat Brain Characterized by High-Affinity [3H]Diazepam Binding . Proc. Natl. Acad. Sci. USA , 74 : 3805 – 3809 .
   PubMed Web of Science ®Google Scholar
• Camerman , A. and Camerman , N. 1972 . Stereochemical Basis of Anticonvulsant Drug Action. II. Molecular Structure of Diazepam . J. Am. Chem. Soc. , 94 : 268 – 272 .
   Google Scholar
• Cartwright , H. M. 1993 . Applications of Artificial Intelligence in Chemistry. , 92 Oxford : Oxford University Press .
   Google Scholar
• Codding , P. W. and Muir , A. K. S. 1985 . Molecular Structure of Ro15–1788 and a Model for the Binding of Benzodiazepine Receptor Ligands . Molec. Pharmacol. , 28 : 178 – 184 .
   PubMed Web of Science ®Google Scholar
• Devillers , J. 1996 . “ Genetic Algorithms in Computer-Aided Molecular Design ” . In Genetic Algorithms in Molecular Modeling , Edited by: Devillers , J. 1 – 34 . London : Academic Press .
   Google Scholar
• Francis , J. E. , Cash , W. D. , Barbaz , B. S. , Bernard , P. S. , Lovell , R. A. , Mazzenga , G. C. , Friedmann , R. C. , Hyun , J. L. , Braunwalder , A. F. , Loo , P. S. and Bennett , D. A. 1991 . Synthesis and Benzodiazepine Binding Activity of a Series of Novel [1,2,4]Triazolo[1,5-c] quinazolin-5(6H)ones . J. Med. Chem. , 34 : 281 – 290 .
   PubMed Web of Science ®Google Scholar
• Goldberg , D. E. 1989 . Genetic Algorithms in Search, Optimization and Machine Learning. , 412 Reading : Addison-Wesley .
   Google Scholar
• Golender , V. , Vesterman , B. and Vorpagel , E. 1996 . Apex-3D Expert System for Drug Design . Network Science , 2
   Google Scholar
• Greene , J. , Kahn , S. , Savoj , H. , Sprague , P. and Teig , S. 1994 . Chemical Function Queries for 3D Database Search . J. Chem. Inf. Comput. Sci. , 34 : 1297 – 1308 .
   Google Scholar
• Hadjipavlou-Litina , D. and Hansch , C. 1994 . Quantitative Structure-Activity Relationships of the Benzodiazepines. A Review and Reevaluation . Chem. Rev. , 24 : 1483 – 1505 .
   Google Scholar
• Haefely , W. E. 1987 . Structure and Function of the Benzodiazepine Receptor . CHIMIA , 41 : 389 – 396 .
   Google Scholar
• Hall , S. R. and Stewart , J. M. 1990 . Xtal 3.0, Reference Manual , Edited by: Hall , S. R. and Stewart , J. M. 408 Perth : Universities of Western Australia and Maryland .
   Google Scholar
• Hempel , A. , Camerman , N. and Camerman , A. 1987 . Benzodiazepine Stereochemistry: Crystal Structures of the Diazepam Antagonist Ro 15–1788 and the Anomalous Benzodiazepine Ro 5–4864 . Can. J. Chem. , 65 : 1608 – 1612 .
   Google Scholar
• Holland , J. H. 1975 . Adaptation in Natural and Artificial Systems. , 211 Cambridge : MIT Press .
   Google Scholar
• Johnson , C. K. 1977 . “ ORCRIT – The Oak Ridge Critical Point Network Program ” . Oak Ridge, TN : Chemistry Division, Oak Ridge National Laboratory .
   Google Scholar
• Kubinyi , H. 1996 . “ A General View on Similarity and QSAR Studies ” . In Computer-Assisted Lead Finding and Optimization , L-1 Book of Abstracts .
   Google Scholar
• Leherte , L. , Fortier , S. , Glasgow , J. and Allen , F. H. 1994 . Molecular Scene Analysis: Application of a Topological Approach to the Automated Interpretation of Protein Electron Density Maps . Acta Cryst. , D50 : 155 – 166 .
   Google Scholar
• Lejeune , J. , Michel , A. G. and Vercauteren , D. P. 1986 . Interactive Flexible Molecular Fitting Program to be Integrated into Computer-Aided Molecular Modelling Systems . J. Mol. Graphics , 4 : 194 – 199 .
   Google Scholar
• Luke , B. T. 1996 . “ An Overview of Genetic Methods ” . In Genetic Algorithms in Molecular Modeling , Edited by: Devillers , J. 35 – 66 . London : Academic Press .
   Google Scholar
• Meurice , N. , Leherte , L. , Vercauteren , D. P. , Bourguignon , J.-J. and Wermuth , C. G. 1997a . “ Development of a Genetic Algorithm Especially Designed for the Comparison of Molecular Models: Application to the Elucidation of the Benzodazepine Receptor Pharmacophore ” . In Computer-Assisted Lead Finding and Optimization , Edited by: van de Waterbeemd , H. , Testa , B. and Folkers , G. 497 – 510 . Basel : Verlag Helvetica Chimica Acta (VHCA) .
   Google Scholar
• Meurice , N. , Norberg , B. , Durant , F. , Didier , B. , Bourguignon , J.-J. , Leherte , L. and Vercauteren , D. P. 1997b . Acta Cryst. , C Submitted for publication
   Google Scholar
• Meza , J. C. , Judson , R. S. , Faulkner , T. R. and Treasurywala , A. M. 1996 . A Comparison of a Direct Search Method and a Genetic Algorithm for Conformational Searching . J. Comput. Chem. , 17 : 1142 – 1151 .
   Web of Science ®Google Scholar
• Rohrer , D. C. 1995 . “ 3D Molecular Similarity Modelling in Computational Drug Design. In, Molecular Similarity and Reactivity ” . In From Quantum Chemical to Phenomenological Approaches , Edited by: Carbo , R. 141 – 161 . Dordrecht : Kluwer Academic .
   Google Scholar
• Sheridan , R. P. and Kearsley , S. K. 1995 . Using a Genetic Algorithm to Suggest Combinatorial Libraries . J. Chem. Inf. Comput. Sci. , 35 : 310 – 320 .
   Google Scholar
• Squires , R. F. and Braestrup , C. 1977 . Benzodiazepine Receptors in Rat Brain . Nature , 266 : 732 – 734 .
   PubMed Web of Science ®Google Scholar
• Tarzia , G. , Occelli , E. , Toja , E. , Barone , D. , Corsico , N. , Gallico , L. and Luzzani , F. 1988 . 6-(Alkylamino)-3-aryl-1,2,4-triazolo[3,4-c]phtalazines. A New Class of Benzodiazepine Receptor Ligands . J. Med. Chem. , 31 : 1115 – 1123 .
   PubMed Web of Science ®Google Scholar
• Tebib , S. , Bourguignon , J.-J. and Wermuth , C. G. 1987 . The Active Analog Approach Applied to the Pharmacophore Identification of Benzodiazepine Receptor Ligands . J. Comp. Aid. Mol. Design , 1 : 153 – 170 .
   PubMedGoogle Scholar
• Walters , D. E. 1995 . When There is no Receptor Crystal Structure: Building Useful Models of Receptor Sites . Network Science , 1
   Google Scholar
• Walters , D. E. and Hinds , E. M. 1994 . Genetically Evolved Receptor Models: A Computational Approach to Construction of Receptor Models . J. Med. Chem. , 37 : 2527 – 2536 .
   PubMed Web of Science ®Google Scholar
• Walters , D. E. and Muhammad , T. D. 1996 . “ Genetically Evolved Receptor Models (GERM): A Procedure for Construction of Atomic-Level Receptor Site Models in the Absence of a Receptor Crystal Structure ” . In Genetic Algorithms in Molecular Modeling , Edited by: Devillers , J. 193 – 210 . London : Academic Press .
   Google Scholar