LEADER 05550nam 22007211 450 001 9910823151403321 005 20240401225220.0 010 $a3-527-66516-1 010 $a3-527-66514-5 010 $a3-527-66517-X 035 $a(CKB)2550000001157308 035 $a(EBL)1524298 035 $a(OCoLC)862371218 035 $a(SSID)ssj0001163812 035 $a(PQKBManifestationID)11743493 035 $a(PQKBTitleCode)TC0001163812 035 $a(PQKBWorkID)11164433 035 $a(PQKB)10707958 035 $a(OCoLC)868979349 035 $a(MiAaPQ)EBC1524298 035 $a(MiAaPQ)EBC4044464 035 $a(Au-PeEL)EBL1524298 035 $a(CaPaEBR)ebr10799628 035 $a(CaONFJC)MIL540351 035 $a(PPN)178872997 035 $a(EXLCZ)992550000001157308 100 $a20131107h20142014 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aScaffold hopping in medicinal chemistry /$fedited by Nathan Brown 205 $a1st ed. 210 1$aWeinheim, Germany :$cWiley-VCH,$d[2014] 210 4$dİ2014 215 $a1 online resource (326 p.) 225 1 $aMethods and principles in medicinal chemistry ;$vvolume 58 300 $aDescription based upon print version of record. 311 $a3-527-33364-9 311 $a1-306-09100-4 320 $aIncludes bibliographical references and index. 327 $aScaffold Hopping in Medicinal Chemistry; Contents; List of Contributors; Preface; A Personal Foreword; Part One: Scaffolds: Identification, Representation Diversity, and Navigation; 1 Identifying and Representing Scaffolds; 1.1 Introduction; 1.2 History of Scaffold Representations; 1.3 Functional versus Structural Molecular Scaffolds; 1.4 Objective and Invariant Scaffold Representations; 1.4.1 Molecular Frameworks; 1.4.2 Scaffold Tree; 1.5 Maximum Common Substructures; 1.6 Privileged Scaffolds; 1.7 Conclusions; References; 2 Markush Structures and Chemical Patents; 2.1 Introduction 327 $a2.2 Encoding Markush Structures2.2.1 The r_group Record; 2.2.1.1 Exact R Groups; 2.2.1.2 Inexact R Groups; 2.2.1.3 Fused R Groups; 2.2.2 The Menguin Program; 2.2.3 Correspondence between the MIL File and the Markush Structure; 2.3 The Search Algorithm; 2.3.1 Matching R Groups; 2.3.1.1 Exact R Groups; 2.3.1.2 Inexact R Groups; 2.3.1.3 Fused R Groups; 2.3.1.4 Hydrogen Atoms; 2.3.1.5 Managing Multiple Fragment/R Group Matches; 2.4 Using Periscope for Scaffold Hopping; 2.4.1 Substructure Searching; 2.4.2 Free-Wilson Analysis; 2.4.3 Fast Followers; 2.5 Conclusions; References 327 $a3 Scaffold Diversity in Medicinal Chemistry Space3.1 Introduction; 3.1.1 Scaffold Representation; 3.1.2 What Do We Mean by Scaffold Diversity?; 3.2 Scaffold Composition of Medicinal Chemistry Space; 3.2.1 Natural Products as a Source of Novel Medicinal Chemistry Scaffolds; 3.2.2 Enumerating Potential Medicinal Chemistry Scaffolds; 3.2.3 Using Scaffold Composition to Interpret Bioactivity Data; 3.3 Metrics for Quantifying the Scaffold Diversity of Medicinal Chemistry Space; 3.4 Visualizing the Scaffold Diversity of Medicinal Chemistry Space; 3.5 Conclusions; References 327 $a4 Scaffold Mining of Publicly Available Compound Data4.1 Introduction; 4.2 Scaffold Definition; 4.3 Selectivity of Scaffolds; 4.3.1 Privileged Substructures; 4.3.2 Target Community-Selective Scaffolds; 4.3.3 Target-Selective Scaffolds; 4.4 Target Promiscuity of Scaffolds; 4.4.1 Promiscuous BM Scaffolds and CSKs; 4.4.2 Scaffold-Target Family Profiles; 4.4.3 Promiscuous Scaffolds in Drugs; 4.5 Activity Cliff-Forming Scaffolds; 4.5.1 Activity Cliff Concept; 4.5.2 Multitarget Cliff-Forming Scaffolds; 4.6 Scaffolds with Defined Activity Progression; 4.6.1 Activity Profile Sequences 327 $a4.6.2 Conserved Scaffolds4.7 Scaffold Diversity of Pharmaceutical Targets; 4.7.1 Scaffold Hopping Potential; 4.7.2 Structural Relationships between Scaffolds; 4.7.3 Scaffold Hopping in Virtual Screening; 4.8 Conclusions; References; 5 Exploring Virtual Scaffold Spaces; 5.1 Introduction; 5.1.1 Virtual Chemistry; 5.1.2 Chemical Space; 5.1.3 Scaffold Definition; 5.2 The Comprehensive Enumeration of Parts of Chemical Space; 5.2.1 Fragments; 5.2.2 Ring Systems; 5.2.3 Reagents; 5.3 The Iterative Generation of Virtual Compounds; 5.3.1 Transformations; 5.3.2 Manual Selection of Chemical Modifications 327 $a5.3.3 Analog Generators 330 $aThis first systematic treatment of the concept and practice of scaffold hopping shows the tricks of the trade and provides invaluable guidance for the reader's own projects.The first section serves as an introduction to the topic by describing the concept of scaffolds, their discovery, diversity and representation, and their importance for finding new chemical entities. The following part describes the most common tools and methods for scaffold hopping, whether topological, shape-based or structure-based. Methods such as CATS, Feature Trees, Feature Point Pharmacophores (FEPOPS), and S 410 0$aMethods and principles in medicinal chemistry ;$vv. 58. 606 $aPharmaceutical chemistry 606 $aDrug interactions 615 0$aPharmaceutical chemistry. 615 0$aDrug interactions. 676 $a615.19 701 $aBrown$b Nathan$0828243 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910823151403321 996 $aScaffold hopping in medicinal chemistry$94014349 997 $aUNINA