Table of Contents
June 30, 2005
Volume 48, Issue 13
Pages 4183-4490
About the Cover: Interaction of the β-L-enantiomer of a 4'-C-ethynyl-2',3'-dideoxynucleoside analogue (ent-14-TP) at the active site of HIV reverse transcriptase (Siddiqui, M. A.; et al. J. Med. Chem. 2004, 47, 5041-5048).
2005 American Chemical Society Award for Computers in Chemical and Pharmaceutical Research
Searching Techniques for Databases of Two- and Three-Dimensional Chemical Structures
Peter Willett
pp 4183–4199Publication Date (Web): May 28, 2005 (Perspective)
DOI: 10.1021/jm0582165
Hi-Res PDF Letters
Two Prodrugs of Potent and Selective GluR5 Kainate Receptor Antagonists Actives in Three Animal Models of Pain
Esteban Dominguez, Smriti Iyengar, Harlan E. Shannon, David Bleakman, Andrew Alt, Brian M. Arnold, Michael G. Bell, Thomas J. Bleisch, Jennifer L. Buckmaster, Ana M. Castano, Miriam Del Prado, Ana Escribano, Sandra A. Filla, Ken H. Ho, Kevin J. Hudziak, Carrie K. Jones, Jose A. Martinez-Perez, Ana Mateo, Brian M. Mathes, Edward L. Mattiuz, Ann Marie L. Ogden, Rosa Maria A. Simmons, Douglas R. Stack, Robert E. Stratford, Mark A. Winter, Zhipei Wu, and Paul L. Ornstein
pp 4200–4203Publication Date (Web): May 21, 2005 (Letter)
DOI: 10.1021/jm0491952
Ligand Binding Analysis for Human α5β1 Integrin: Strategies for Designing New α5β1 Integrin Antagonists
Luciana Marinelli, Axel Meyer, Dominik Heckmann, Antonio Lavecchia, Ettore Novellino, and Horst Kessler
pp 4204–4207Publication Date (Web): June 01, 2005 (Letter)
DOI: 10.1021/jm040224i
1-Acyl-1H-[1,2,4]triazole-3,5-diamine Analogues as Novel and Potent Anticancer Cyclin-Dependent Kinase Inhibitors: Synthesis and Evaluation of Biological Activities
Ronghui Lin, Peter J. Connolly, Shenlin Huang, Steven K. Wetter, Yanhua Lu, William V. Murray, Stuart L. Emanuel, Robert H. Gruninger, Angel R. Fuentes-Pesquera, Catherine A. Rugg, Steven A. Middleton, and Linda K. Jolliffe
pp 4208–4211Publication Date (Web): June 03, 2005 (Letter)
DOI: 10.1021/jm050267e
Novel, Potent Small-Molecule Inhibitors of the Molecular Chaperone Hsp90 Discovered through Structure-Based Design
Brian W. Dymock, Xavier Barril, Paul A. Brough, Julie E. Cansfield, Andrew Massey, Edward McDonald, Roderick E. Hubbard, Allan Surgenor, Stephen D. Roughley, Paul Webb, Paul Workman, Lisa Wright, and Martin J. Drysdale
pp 4212–4215Publication Date (Web): June 02, 2005 (Letter)
DOI: 10.1021/jm050355z
A Three-Dimensional Pharmacophore Model for 5-Hydroxytryptamine6 (5-HT6) Receptor Antagonists
María L. López-Rodríguez, Bellinda Benhamú, Tania de la Fuente, Arantxa Sanz, Leonardo Pardo, and Mercedes Campillo
pp 4216–4219Publication Date (Web): June 03, 2005 (Letter)
DOI: 10.1021/jm050247c
Design, Synthesis, and Biological Activities of Pyrrolylethanoneamine Derivatives, a Novel Class of Monoamine Oxidases Inhibitors
Roberto Di Santo, Roberta Costi, Alessandra Roux, Marino Artico, Olivia Befani, Tiziana Meninno, Enzo Agostinelli, Paola Palmegiani, Paola Turini, Roberto Cirilli, Rosella Ferretti, Bruno Gallinella, and Francesco La Torre
pp 4220–4223Publication Date (Web): June 03, 2005 (Letter)
DOI: 10.1021/jm050172c
Articles
Peptoid−Peptide Hybrids as Potent Novel Melanocortin Receptor Ligands
John A. W. Kruijtzer, Wouter A. J. Nijenhuis, Nienke Wanders, Willem Hendrik Gispen, Rob M. J. Liskamp, and Roger A. H. Adan
pp 4224–4230Publication Date (Web): May 25, 2005 (Article)
DOI: 10.1021/jm0490033
Synthesis and Ocular Effects of Imidazole Nitrolic Acids
Larisa Oresmaa, Hanna Kotikoski, Matti Haukka, Johanna Salminen, Olli Oksala, Esko Pohjala, Eeva Moilanen, Heikki Vapaatalo, Pirjo Vainiotalo, and Paula Aulaskari
pp 4231–4236Publication Date (Web): May 13, 2005 (Article)
DOI: 10.1021/jm048949+
Full Text HTMLFunctionalized Pyrrolidines Inhibit α-Mannosidase Activity and Growth of Human Glioblastoma and Melanoma Cells
Hélène Fiaux, Florence Popowycz, Sylvain Favre, Catherine Schütz, Pierre Vogel, Sandrine Gerber-Lemaire, and Lucienne Juillerat-Jeanneret
pp 4237–4246Publication Date (Web): June 01, 2005 (Article)
DOI: 10.1021/jm0409019
Positional Effect of Chemical Modifications on Short Interference RNA Activity in Mammalian Cells
Thazha P. Prakash, Charles R. Allerson, Prasad Dande, Timothy A. Vickers, Namir Sioufi, Russell Jarres, Brenda F. Baker, Eric E. Swayze, Richard H. Griffey, and Balkrishen Bhat
pp 4247–4253Publication Date (Web): May 27, 2005 (Article)
DOI: 10.1021/jm050044o
Synthesis, in Vitro Characterization, and Radiolabeling of N,N-Dimethyl-2-(2‘-amino-4‘-substituted-phenylthio)benzylamines: Potential Candidates as Selective Serotonin Transporter Radioligands
Nachwa Jarkas, Jonathan McConathy, Ronald J. Voll, and Mark M. Goodman
pp 4254–4265Publication Date (Web): June 04, 2005 (Article)
DOI: 10.1021/jm050079o
Reversion of Human Pgp-Dependent Multidrug Resistance by New Sesquiterpenes from Zinowiewia costaricensis
Francisco Muñoz-Martínez, Cristina R. Mendoza, Isabel L. Bazzocchi, Santiago Castanys, Ignacio A. Jiménez, and Francisco Gamarro
pp 4266–4275Publication Date (Web): June 02, 2005 (Article)
DOI: 10.1021/jm058003f
First Synthesis and Evaluation of the Inhibitory Effects of Aza Analogues of TSAO on HIV-1 Replication
Albert Nguyen Van Nhien, Cyrille Tomassi, Christophe Len, José Luis Marco-Contelles, Jan Balzarini, Christophe Pannecouque, Erik De Clercq, and Denis Postel
pp 4276–4284Publication Date (Web): May 26, 2005 (Article)
DOI: 10.1021/jm050091g
Synthesis and Biological Activity of Nitronyl Nitroxide Containing Peptides
Ming Zhao, Junling Liu, Chao Wang, Lili Wang, Hu Liu, and Shiqi Peng
pp 4285–4292Publication Date (Web): June 03, 2005 (Article)
DOI: 10.1021/jm050050k
Studies on the Apoptotic Activity of Natural and Synthetic Retinoids: Discovery of a New Class of Synthetic Terphenyls That Potently Support Cell Growth and Inhibit Apoptosis in Neuronal and HL-60 Cells
Daniele Simoni, Giuseppe Giannini, Marinella Roberti, Riccardo Rondanin, Riccardo Baruchello, Marcello Rossi, Giuseppina Grisolia, Francesco Paolo Invidiata, Stefania Aiello, Silvia Marino, Sabrina Cavallini, Anna Siniscalchi, Nicola Gebbia, Lucia Crosta, Stefania Grimaudo, Vincenzo Abbadessa, Antonietta Di Cristina, and Manlio Tolomeo
pp 4293–4299Publication Date (Web): June 03, 2005 (Article)
DOI: 10.1021/jm049080y
Synthesis and Evaluation of (17α,20Z)-21-(4-Substituted-phenyl)-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols as Ligands for the Estrogen Receptor-α Hormone Binding Domain: Comparison with 20E-Isomers
Robert N. Hanson, Carolyn J. Friel, Robert Dilis, Alun Hughes, and Eugene R. DeSombre
pp 4300–4311Publication Date (Web): June 02, 2005 (Article)
DOI: 10.1021/jm040157s
2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors
Marcello Allegretti, Riccardo Bertini, Maria Candida Cesta, Cinzia Bizzarri, Rosa Di Bitondo, Vito Di Cioccio, Emanuela Galliera, Valerio Berdini, Alessandra Topai, Giuseppe Zampella, Vincenzo Russo, Nicoletta Di Bello, Giuseppe Nano, Luca Nicolini, Massimo Locati, Piercarlo Fantucci, Saverio Florio, and Francesco Colotta
pp 4312–4331Publication Date (Web): May 27, 2005 (Article)
DOI: 10.1021/jm049082i
Structure-Based Design of Novel Chk1 Inhibitors: Insights into Hydrogen Bonding and Protein−Ligand Affinity
Nicolas Foloppe, Lisa M. Fisher, Rob Howes, Peter Kierstan, Andrew Potter, Alan G. S. Robertson, and Allan E. Surgenor
pp 4332–4345Publication Date (Web): May 25, 2005 (Article)
DOI: 10.1021/jm049022c
Quinic Acid Derivatives as Sialyl Lewisx-Mimicking Selectin Inhibitors: Design, Synthesis, and Crystal Structure in Complex with E-Selectin
Neelu Kaila, William S. Somers, Bert E. Thomas, Paresh Thakker, Kristin Janz, Silvano DeBernardo, Steve Tam, William J. Moore, Ruiyang Yang, Wojciech Wrona, Patricia W. Bedard, Deidre Crommie, James C. Keith, Jr., Desiree H. H. Tsao, Juan C. Alvarez, Heyu Ni, Erik Marchese, John T. Patton, John L. Magnani, and Raymond T. Camphausen
pp 4346–4357Publication Date (Web): May 25, 2005 (Article)
DOI: 10.1021/jm050049l
A Robust Clustering Method for Chemical Structures
Martin Stahl, Harald Mauser, Mark Tsui, and Neil R. Taylor
pp 4358–4366Publication Date (Web): June 02, 2005 (Article)
DOI: 10.1021/jm040213p
Pyrrolo[1,5]benzoxa(thia)zepines as a New Class of Potent Apoptotic Agents. Biological Studies and Identification of an Intracellular Location of Their Drug Target
Margaret M. Mc Gee, Sandra Gemma, Stefania Butini, Anna Ramunno, Daniela M. Zisterer, Caterina Fattorusso, Bruno Catalanotti, Gagan Kukreja, Isabella Fiorini, Claudio Pisano, Carla Cucco, Ettore Novellino, Vito Nacci, D. Clive Williams, and Giuseppe Campiani
pp 4367–4377Publication Date (Web): May 27, 2005 (Article)
DOI: 10.1021/jm049402y
Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation
Gabriella De Martino, Giuseppe La Regina, Alessandra Di Pasquali, Rino Ragno, Alberto Bergamini, Chiara Ciaprini, Anna Sinistro, Giovanni Maga, Emmanuele Crespan, Marino Artico, and Romano Silvestri
pp 4378–4388Publication Date (Web): May 27, 2005 (Article)
DOI: 10.1021/jm050273a
Pharmacophore, Drug Metabolism, and Pharmacokinetics Models on Non-Peptide AT1, AT2, and AT1/AT2 Angiotensin II Receptor Antagonists
Giuliano Berellini, Gabriele Cruciani, and Raimund Mannhold
pp 4389–4399Publication Date (Web): June 03, 2005 (Article)
DOI: 10.1021/jm049024x
Design and Synthesis of Potent Inhibitors of Plasmepsin I and II: X-ray Crystal Structure of Inhibitor in Complex with Plasmepsin II
Per-Ola Johansson, Jimmy Lindberg, Michael J. Blackman, Ingemar Kvarnström, Lotta Vrang, Elizabeth Hamelink, Anders Hallberg, Åsa Rosenquist, and Bertil Samuelsson
pp 4400–4409Publication Date (Web): June 02, 2005 (Article)
DOI: 10.1021/jm040884n
Three-Dimensional Quantitative Structure−Activity Relationship Analyses of β-Lactam Antibiotics and Tripeptides as Substrates of the Mammalian H+/Peptide Cotransporter PEPT1
Annegret Biegel, Sabine Gebauer, Bianka Hartrodt, Matthias Brandsch, Klaus Neubert, and Iris Thondorf
pp 4410–4419Publication Date (Web): May 26, 2005 (Article)
DOI: 10.1021/jm048982w
Design, Synthesis, and Antifolate Activity of New Analogues of Piritrexim and Other Diaminopyrimidine Dihydrofolate Reductase Inhibitors with ω-Carboxyalkoxy or ω-Carboxy-1-alkynyl Substitution in the Side Chain
David C. M. Chan, Hongning Fu, Ronald A. Forsch, Sherry F. Queener, and Andre Rosowsky
pp 4420–4431Publication Date (Web): June 07, 2005 (Article)
DOI: 10.1021/jm0581718
Unveiling the Full Potential of Flexible Receptor Docking Using Multiple Crystallographic Structures
Xavier Barril and S. David Morley
pp 4432–4443Publication Date (Web): May 24, 2005 (Article)
DOI: 10.1021/jm048972v
Cholinesterase Inhibitors: Xanthostigmine Derivatives Blocking the Acetylcholinesterase-Induced β-Amyloid Aggregation
Federica Belluti, Angela Rampa, Lorna Piazzi, Alessandra Bisi, Silvia Gobbi, Manuela Bartolini, Vincenza Andrisano, Andrea Cavalli, Maurizio Recanatini, and Piero Valenti
pp 4444–4456Publication Date (Web): May 27, 2005 (Article)
DOI: 10.1021/jm049515h
Design and Synthesis of α-Aryloxyphenylacetic Acid Derivatives: A Novel Class of PPARα/γ Dual Agonists with Potent Antihyperglycemic and Lipid Modulating Activity
Guo Q. Shi, James F. Dropinski, Brian M. McKeever, Shihua Xu, Joseph W. Becker, Joel P. Berger, Karen L. MacNaul, Alex Elbrecht, Gaochao Zhou, Thomas W. Doebber, Peiran Wang, Yu-Sheng Chao, Mike Forrest, James V. Heck, David E. Moller, and A. Brian Jones
pp 4457–4468Publication Date (Web): June 04, 2005 (Article)
DOI: 10.1021/jm0502135
Discovery of Potent Anilide Inhibitors against the Severe Acute Respiratory Syndrome 3CL Protease
Jiun-Jie Shie, Jim-Min Fang, Chih-Jung Kuo, Tun-Hsun Kuo, Po-Huang Liang, Hung-Jyun Huang, Wen-Bin Yang, Chun-Hung Lin, Jiun-Ling Chen, Yin-Ta Wu, and Chi-Huey Wong
pp 4469–4473Publication Date (Web): June 04, 2005 (Article)
DOI: 10.1021/jm050184y
A New Synthetic Agent with Potent but Selective Cytotoxic Activity against Cancer
Wieslaw M. Cholody, Teresa Kosakowska-Cholody, Melinda G. Hollingshead, Humcha K. Hariprakasha, and Christopher. J. Michejda
pp 4474–4481Publication Date (Web): June 08, 2005 (Article)
DOI: 10.1021/jm048946x
Brief Articles
Modeling of Purine Derivatives Transport across Cell Membranes Based on Their Partition Coefficient Determination and Quantum Chemical Calculations
Marcin Hoffmann, Maria Chrzanowska, Tadeusz Hermann, and Jacek Rychlewski
pp 4482–4486Publication Date (Web): May 27, 2005 (Brief Article)
DOI: 10.1021/jm0495273
Book Reviews
Name Reactions in Heterocyclic Chemistry Edited by Jie-Jack Li. John Wiley & Sons, Hoboken, NJ. 2005. xix + 558 pp. 19 × 24 cm. ISBN 0-471-30215-5. $125.00.
Ronald F. Borne
p 4487Publication Date (Web): June 03, 2005 (Book Review)
DOI: 10.1021/jm058210f
Predicting Chemical Toxicity and Fate Edited by Mark T. D. Cronin and David J. Livingstone. CRC Press, Boca Raton, FL. 2004. xviii + 445 pp. 18 × 26 cm. ISBN 0-415-27180-0. $98.95.
Gordon G. Cash
pp 4487–4488Publication Date (Web): June 03, 2005 (Book Review)
DOI: 10.1021/jm0582266
Mechanisms in Organic Reactions By Richard A. Jackson. The Royal Society of Chemistry, Cambridge, U.K. 2004. vi + 199 pp. 19 × 24.5 cm. ISBN 0-85404-642-9. £14.95.
Robert J. Kerns
p 4488Publication Date (Web): May 28, 2005 (Book Review)
DOI: 10.1021/jm058229i
Additions and Corrections
Synthesis and Evaluation of (Pyridylmethylene)tetrahydronaphthalenes/-indanes and Structurally Modified Derivatives: Potent and Selective Inhibitors of Aldosterone Synthase
Sarah Ulmschneider, Ursula Müller-Vieira, Christian D. Klein, Iris Antes, Thomas Lengauer, Rolf W. Hartmann:
pp 4489–4490Publication Date (Web): May 19, 2005 (Addition/Correction)
DOI: 10.1021/jm058022p