Table of Contents
June 3, 2004
Volume 47, Issue 12
Pages 2945-3328
About the Cover: Molecular modeling of overlayed trisubstituted acridine derivatives (mauve and green) complexed with G-quadruplex DNA (Harrison, R. J.; et al. J. Med. Chem. 2003, 46, 4463-4476).
Perspective
A Medicinal Chemistry Perspective on Artemisinin and Related Endoperoxides
Paul M. O'Neill and Gary H. Posner
pp 2945–2964Publication Date (Web): May 12, 2004 (Perspective)
DOI: 10.1021/jm030571c
Hi-Res PDF Letters
Synthesis and Antibacterial Activity of a Novel Class of 4‘-Substituted 16-Membered Ring Macrolides Derived from Tylosin
Ly T. Phan, Tianying Jian, Zhigang Chen, Yao-Ling Qiu, Zhaolin Wang, Theresa Beach, Alex Polemeropoulos, and Yat Sun Or
pp 2965–2968Publication Date (Web): May 4, 2004 (Letter)
DOI: 10.1021/jm034233n
A Bivalent Ligand (KDN-21) Reveals Spinal δ and κ Opioid Receptors Are Organized as Heterodimers That Give Rise to δ1 and κ2 Phenotypes. Selective Targeting of δ−κ Heterodimers
Rashmi G. Bhushan, Shiv K. Sharma, Zhihua Xie, David J. Daniels, and Philip S. Portoghese
pp 2969–2972Publication Date (Web): May 8, 2004 (Letter)
DOI: 10.1021/jm0342358
A Novel Series of Piperidin-4-yl-1,3-Dihydroindol-2-ones as Agonist and Antagonist Ligands at the Nociceptin Receptor
Nurulain T. Zaveri, Faming Jiang, Cris M. Olsen, Jeffrey R. Deschamps, Damon Parrish, Willma Polgar, and Lawrence Toll
pp 2973–2976Publication Date (Web): May 4, 2004 (Letter)
DOI: 10.1021/jm034249d
The PDBbind Database: Collection of Binding Affinities for Protein−Ligand Complexes with Known Three-Dimensional Structures
Renxiao Wang, Xueliang Fang, Yipin Lu, and Shaomeng Wang
pp 2977–2980Publication Date (Web): May 4, 2004 (Letter)
DOI: 10.1021/jm030580l
Sultam Hydroxamates as Novel Matrix Metalloproteinase Inhibitors
Robert J. Cherney, Ruowei Mo, Dayton T. Meyer, Karl D. Hardman, Rui-Qin Liu, Maryanne B. Covington, Mingxin Qian, Zelda R. Wasserman, David D. Christ, James M. Trzaskos, Robert C. Newton, and Carl P. Decicco
pp 2981–2983Publication Date (Web): May 8, 2004 (Letter)
DOI: 10.1021/jm049833g
Articles
Antiproliferative and Phenotype-Transforming Antitumor Agents Derived from Cysteine
Matthew P. Glenn, Pia Kahnberg, Glen M. Boyle, Karl A. Hansford, Dhiraj Hans, Adam C. Martyn, Peter G. Parsons, and David P. Fairlie
pp 2984–2994Publication Date (Web): April 29, 2004 (Article)
DOI: 10.1021/jm030222i
Discovery and Evaluation of Potent P1 Aryl Heterocycle-Based Thrombin Inhibitors
Mary Beth Young, James C. Barrow, Kristen L. Glass, George F. Lundell, Christina L. Newton, Janetta M. Pellicore, Kenneth E. Rittle, Harold G. Selnick, Kenneth J. Stauffer, Joseph P. Vacca, Peter D. Williams, Dennis Bohn, Franklin C. Clayton, Jacquelynn J. Cook, Julie A. Krueger, Lawrence C. Kuo, S. Dale Lewis, Bobby J. Lucas, Daniel R. McMasters, Cynthia Miller-Stein, Beth L. Pietrak, Audrey A. Wallace, Rebecca B. White, Bradley Wong, Youwei Yan, and Philippe G. Nantermet
pp 2995–3008Publication Date (Web): May 8, 2004 (Article)
DOI: 10.1021/jm030303e
Synthesis, Molecular Modeling, and Biological Studies of Novel Piperidine-Based Analogues of Cocaine: Evidence of Unfavorable Interactions Proximal to the 3α-Position of the Piperidine Ring
Pavel A. Petukhov, Jianrong Zhang, Cheng Z. Wang, Yan Ping Ye, Kenneth M. Johnson, and Alan P. Kozikowski
pp 3009–3018Publication Date (Web): May 12, 2004 (Article)
DOI: 10.1021/jm0303296
Study on Affinity Profile toward Native Human and Bovine Adenosine Receptors of a Series of 1,8-Naphthyridine Derivatives
Pier Luigi Ferrarini, Laura Betti, Tiziana Cavallini, Gino Giannaccini, Antonio Lucacchini, Clementina Manera, Adriano Martinelli, Gabriella Ortore, Giuseppe Saccomanni, and Tiziano Tuccinardi
pp 3019–3031Publication Date (Web): May 11, 2004 (Article)
DOI: 10.1021/jm030977p
Assessing Scoring Functions for Protein−Ligand Interactions
Philippe Ferrara, Holger Gohlke, Daniel J. Price, Gerhard Klebe, and Charles L. Brooks III
pp 3032–3047Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm030489h
Development of a 3D Model for the Human Cannabinoid CB1 Receptor
Outi M. H. Salo, Maija Lahtela-Kakkonen, Jukka Gynther, Tomi Järvinen, and Antti Poso
pp 3048–3057Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm031052c
Anti-HIV Activity and Conformational Studies of Peptides Derived from the C-Terminal Sequence of SDF-1
Monica Dettin, Antonella Pasquato, Claudia Scarinci, Marisa Zanchetta, Anita De Rossi, and Carlo Di Bello
pp 3058–3064Publication Date (Web): May 7, 2004 (Article)
DOI: 10.1021/jm031067a
A Molecular Basis for the Selectivity of Thiadiazole Urea Inhibitors with Stromelysin-1 and Gelatinase-A from Generalized Born Molecular Dynamics Simulations
Robert C. Rizzo, Samuel Toba, and Irwin D. Kuntz
pp 3065–3074Publication Date (Web): April 28, 2004 (Article)
DOI: 10.1021/jm030570k
Characterization of a Ligand−Receptor Binding Event Using Receptor-Dependent Four-Dimensional Quantitative Structure−Activity Relationship Analysis
Dahua Pan, Jianzhong Liu, Craig Senese, Anton J. Hopfinger, and Yufeng Tseng
pp 3075–3088Publication Date (Web): April 24, 2004 (Article)
DOI: 10.1021/jm030586a
New Series of Morpholine and 1,4-Oxazepane Derivatives as Dopamine D4 Receptor Ligands: Synthesis and 3D-QSAR Model
Karine Audouze, Elsebet Østergaard Nielsen, and Dan Peters
pp 3089–3104Publication Date (Web): May 5, 2004 (Article)
DOI: 10.1021/jm031111m
Synthesis and Quantitative Structure−Activity Relationship of Hydrazones of N-Amino-N‘-hydroxyguanidine as Electron Acceptors for Xanthine Oxidase
Peteris Prusis, Maija Dambrova, Victor Andrianov, Eugene Rozhkov, Valentina Semenikhina, Irena Piskunova, Enock Ongwae, Torbjörn Lundstedt, Ivars Kalvinsh, and Jarl E. S. Wikberg
pp 3105–3110Publication Date (Web): May 8, 2004 (Article)
DOI: 10.1021/jm031127c
Integrating Fragment Assembly and Biophysical Methods in the Chemical Advancement of Small-Molecule Antagonists of IL-2: An Approach for Inhibiting Protein−Protein Interactions
Brian C. Raimundo, Johan D. Oslob, Andrew C. Braisted, Jennifer Hyde, Robert S. McDowell, Mike Randal, Nathan D. Waal, Jennifer Wilkinson, Chul H. Yu, and Michelle R. Arkin
pp 3111–3130Publication Date (Web): May 7, 2004 (Article)
DOI: 10.1021/jm049967u
Conformationally Constrained Peptide Analogues of pTyr-Glu-Glu-Ile as Inhibitors of the Src SH2 Domain Binding
Nguyen-Hai Nam, Guofeng Ye, Gongqin Sun, and Keykavous Parang
pp 3131–3141Publication Date (Web): May 11, 2004 (Article)
DOI: 10.1021/jm040008+
Full Text HTMLSDOCKER: A Method Utilizing Existing X-ray Structures To Improve Docking Accuracy
Guosheng Wu and Michal Vieth
pp 3142–3148Publication Date (Web): May 7, 2004 (Article)
DOI: 10.1021/jm040015y
Design, Synthesis, Anti-HIV Activities, and Metabolic Stabilities of Alkenyldiarylmethane (ADAM) Non-nucleoside Reverse Transcriptase Inhibitors
Maximilian A. Silvestri, Muthukaman Nagarajan, Erik De Clercq, Christophe Pannecouque, and Mark Cushman
pp 3149–3162Publication Date (Web): May 12, 2004 (Article)
DOI: 10.1021/jm049916x
Synthesis and Structure−Activity Relationships of a Novel Series of 2,3,5,6,7,9-Hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide KATP Channel Openers: Discovery of (−)-(9S)-9-(3-Bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide (A-278637), a Potent KATP Opener That Selectively Inhibits Spontaneous Bladder Contractions
William A. Carroll, Robert J. Altenbach, Hao Bai, Jorge D. Brioni, Michael E. Brune, Steven A. Buckner, Christopher Cassidy, Yiyuan Chen, Michael J. Coghlan, Anthony V. Daza, Irene Drizin, Thomas A. Fey, Michael Fitzgerald, Murali Gopalakrishnan, Robert J. Gregg, Rodger F. Henry, Mark W. Holladay, Linda L. King, Michael E. Kort, Philip R. Kym, Ivan Milicic, Rui Tang, Sean C. Turner, Kristi L. Whiteaker, Lin Yi, Henry Zhang, and James P. Sullivan
pp 3163–3179Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm030356w
Synthesis and Structure−Activity Relationships of a Novel Series of Tricyclic Dihydropyridine-Based KATP Openers That Potently Inhibit Bladder Contractions in Vitro
William A. Carroll, Konstantinos A. Agrios, Robert J. Altenbach, Steven A. Buckner, Yiyuan Chen, Michael J. Coghlan, Anthony V. Daza, Irene Drizin, Murali Gopalakrishnan, Rodger F. Henry, Michael E. Kort, Philip R. Kym, Ivan Milicic, Jamie C. Smith, Rui Tang, Sean C. Turner, Kristi L. Whiteaker, Henry Zhang, and James P. Sullivan
pp 3180–3192Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm030357o
Chemometric Studies on the Bactericidal Activity of Quinolones via an Extended VolSurf Approach
Giovanni Cianchetta, Raimund Mannhold, Gabriele Cruciani, Massimo Baroni, and Violetta Cecchetti
pp 3193–3201Publication Date (Web): May 7, 2004 (Article)
DOI: 10.1021/jm030986y
Arylcyanoguanidines as Activators of Kir6.2/SUR1KATP Channels and Inhibitors of Insulin Release
Tina M. Tagmose, Søren C. Schou, John P. Mogensen, Flemming E. Nielsen, Per O. G. Arkhammar, Philip Wahl, Birgit S. Hansen, Anne Worsaae, Harrie C. M. Boonen, Marie-Hélène Antoine, Philippe Lebrun, and John Bondo Hansen
pp 3202–3211Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm031018y
Synthesis and Structure−Activity Relationships of Parasiticidal Thiosemicarbazone Cysteine Protease Inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi
Doron C. Greenbaum, Zachary Mackey, Elizabeth Hansell, Patricia Doyle, Jiri Gut, Conor R. Caffrey, Julia Lehrman, Philip J. Rosenthal, James H. McKerrow, and Kelly Chibale
pp 3212–3219Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm030549j
Synthesis and Structure−Activity Studies on N-[5-(1H-Imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an Imidazole-Containing α1A-Adrenoceptor Agonist1
Robert J. Altenbach, Albert Khilevich, Teodozyj Kolasa, Jeffrey J. Rohde, Pramila A. Bhatia, Meena V. Patel, Xenia B. Searle, Fan Yang, William H. Bunnelle, Karin Tietje, Erol K. Bayburt, William A. Carroll, Michael D. Meyer, Rodger Henry, Steven A. Buckner, Jane Kuk, Anthony V. Daza, Ivan V. Milicic, John C. Cain, Chae H. Kang, Lynne M. Ireland, Tracy L. Carr, Thomas R. Miller, Arthur A. Hancock, Masaki Nakane, Timothy A. Esbenshade, Michael E. Brune, Alyssa B. O'Neill, Donna M. Gauvin, Sweta P. Katwala, Mark W. Holladay, Jorge D. Brioni, and James P. Sullivan
pp 3220–3235Publication Date (Web): May 11, 2004 (Article)
DOI: 10.1021/jm030551a
Generation of New Protein Kinase Inhibitors Utilizing Cytochrome P450 Mutant Enzymes for Indigoid Synthesis
F. Peter Guengerich, Jennifer L. Sorrells, Sophie Schmitt, Joel A. Krauser, Pramod Aryal, and Laurent Meijer
pp 3236–3241Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm030561b
Synthesis and Biological Evaluation of 14-Alkoxymorphinans. 21.1 Novel 4-Alkoxy and 14-Phenylpropoxy Derivatives of the μ Opioid Receptor Antagonist Cyprodime
Mariana Spetea, Falko Schüllner, Radu C. Moisa, Ilona P. Berzetei-Gurske, Barbara Schraml, Cynthia Dörfler, Mario D. Aceto, Louis S. Harris, Andrew Coop, and Helmut Schmidhammer
pp 3242–3247Publication Date (Web): May 8, 2004 (Article)
DOI: 10.1021/jm031126k
Conformationally Constrained Analogues of Diacylglycerol. 21. A Solid-Phase Method of Synthesis of Diacylglycerol Lactones as a Prelude to a Combinatorial Approach for the Synthesis of Protein Kinase C Isozyme-Specific Ligands
Dehui Duan, Nancy E. Lewin, Dina M. Sigano, Peter M. Blumberg, and Victor E. Marquez
pp 3248–3254Publication Date (Web): May 7, 2004 (Article)
DOI: 10.1021/jm030610k
(2R)-2-Ethylchromane-2-carboxylic Acids: Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents
Hiroo Koyama, Daniel J. Miller, Julia K. Boueres, Ranjit C. Desai, A. Brian Jones, Joel P. Berger, Karen L. MacNaul, Linda J. Kelly, Thomas W. Doebber, Margaret S. Wu, Gaochao Zhou, Pei-ran Wang, Marc C. Ippolito, Yu-Sheng Chao, Arun K. Agrawal, Ronald Franklin, James V. Heck, Samuel D. Wright, David E. Moller, and Soumya P. Sahoo
pp 3255–3263Publication Date (Web): May 7, 2004 (Article)
DOI: 10.1021/jm030621d
Meta-Substituted Aryl(thio)ethers as Potent Partial Agonists (or Antagonists) for the Histamine H3 Receptor Lacking a Nitrogen Atom in the Side Chain
Nadia Pelloux-Léon, Abdellatif Fkyerat, Antonia Piripitsi, Wasyl Tertiuk, Walter Schunack, Holger Stark, Monique Garbarg, Xavier Ligneau, Jean-Michel Arrang, Jean-Charles Schwartz, and C. Robin Ganellin
pp 3264–3274Publication Date (Web): May 8, 2004 (Article)
DOI: 10.1021/jm031141p
Targeting the Polyamine Pathway with Transition-State Analogue Inhibitors of 5‘-Methylthioadenosine Phosphorylase
Gary B. Evans, Richard H. Furneaux, Vern L. Schramm, Vipender Singh, and Peter C. Tyler
pp 3275–3281Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm0306475
Design, Synthesis, and Structure−Activity Relationships of Haloenol Lactones: Site-Directed and Isozyme-Selective Glutathione S-Transferase Inhibitors
Zhixing Wu, Gurpreet Singh Minhas, Dingyi Wen, Hualiang Jiang, Kaixian Chen, Piotr Zimniak, and Jiang Zheng
pp 3282–3294Publication Date (Web): May 4, 2004 (Article)
DOI: 10.1021/jm0499615
Aziridinyldinitrobenzamides: Synthesis and Structure−Activity Relationships for Activation by E. coli Nitroreductase
Nuala A. Helsby, Graham J. Atwell, Shangjin Yang, Brian D. Palmer, Robert F. Anderson, Susan M. Pullen, Dianne M. Ferry, Alison Hogg, William R. Wilson, and William A. Denny
pp 3295–3307Publication Date (Web): May 12, 2004 (Article)
DOI: 10.1021/jm0498699
Mitomycin Dimers: Polyfunctional Cross-Linkers of DNA
Manuel M. Paz, Gopinatha Suresh Kumar, Mark Glover, Michael J. Waring, and Maria Tomasz
pp 3308–3319Publication Date (Web): May 1, 2004 (Article)
DOI: 10.1021/jm049863j
Brief Articles
2-Aminopyridines as Highly Selective Inducible Nitric Oxide Synthase Inhibitors. Differential Binding Modes Dependent on Nitrogen Substitution
Stephen Connolly, Anders Aberg, Andrew Arvai, Haydn G. Beaton, David R. Cheshire, Anthony R. Cook, Sally Cooper, David Cox, Peter Hamley, Phil Mallinder, Ian Millichip, David J. Nicholls, Robin J. Rosenfeld, Stephen A. St-Gallay, John Tainer, Alan C. Tinker, and Alan V. Wallace
pp 3320–3323Publication Date (Web): May 7, 2004 (Brief Article)
DOI: 10.1021/jm031035n
Development of a New Type of Allosteric Modulator of Muscarinic Receptors: Hybrids of the Antagonist AF-DX 384 and the Hexamethonio Derivative W84
Marion Mohr, Eberhard Heller, Ameneh Ataie, Klaus Mohr, and Ulrike Holzgrabe
pp 3324–3327Publication Date (Web): May 7, 2004 (Brief Article)
DOI: 10.1021/jm031095t
Book Reviews
Molecular Modelling for Beginners By Alan Hinchliffe. Wiley, Chichester, U.K. 2003. xviii + 410 pp. 17 × 24.5 cm. ISBN 0-4708-4310-1. $35.00.
David J. Livingstone
p 3328Publication Date (Web): May 8, 2004 (Book Review)
DOI: 10.1021/jm0400698