Table of Contents
February 24, 2005
Volume 48, Issue 4
Pages 897-1296
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).
Letters
Minor Structural Modifications Convert the Dual TP/CRTH2 Antagonist Ramatroban into a Highly Selective and Potent CRTH2 Antagonist
Trond Ulven and Evi Kostenis
pp 897–900Publication Date (Web): January 27, 2005 (Letter)
DOI: 10.1021/jm049036i
Hi-Res PDFFully 2‘-Modified Oligonucleotide Duplexes with Improved in Vitro Potency and Stability Compared to Unmodified Small Interfering RNA
Charles R. Allerson, Namir Sioufi, Russell Jarres, Thazha P. Prakash, Nishant Naik, Andres Berdeja, Lisa Wanders, Richard H. Griffey, Eric E. Swayze, and Balkrishen Bhat
pp 901–904Publication Date (Web): January 20, 2005 (Letter)
DOI: 10.1021/jm049167j
Discovery and Structure−Activity Relationship of Quinuclidine Benzamides as Agonists of α7 Nicotinic Acetylcholine Receptors
Alice L. Bodnar, Luz A. Cortes-Burgos, Karen K. Cook, Dac M. Dinh, Vincent E. Groppi, Mihaly Hajos, Nicole R. Higdon, William E. Hoffmann, Raymond S. Hurst, Jason K. Myers, Bruce N. Rogers, Theron M. Wall, Mark L. Wolfe, and Erik Wong
pp 905–908Publication Date (Web): January 21, 2005 (Letter)
DOI: 10.1021/jm049363q
Discovery and Cocrystal Structure of Benzodiazepinedione HDM2 Antagonists That Activate p53 in Cells
Bruce L. Grasberger, Tianbao Lu, Carsten Schubert, Daniel J. Parks, Theodore E. Carver, Holly K. Koblish, Maxwell D. Cummings, Louis V. LaFrance, Karen L. Milkiewicz, Raul R. Calvo, Diane Maguire, Jennifer Lattanze, Carol F. Franks, Shuyuan Zhao, Kannan Ramachandren, Gwendolyn R. Bylebyl, Marie Zhang, Carl L. Manthey, Eugene C. Petrella, Michael W. Pantoliano, Ingrid C. Deckman, John C. Spurlino, Anna C. Maroney, Bruce E. Tomczuk, Christopher J. Molloy, and Roger F. Bone
pp 909–912Publication Date (Web): February 01, 2005 (Letter)
DOI: 10.1021/jm049137g
Improving Specificity vs Bacterial Thymidylate Synthases through N-Dansyl Modulation of Didansyltyrosine
Donatella Tondi, Alberto Venturelli, Stefania Ferrari, Stefano Ghelli, and M. Paola Costi
pp 913–916Publication Date (Web): February 02, 2005 (Letter)
DOI: 10.1021/jm0491445
Articles
Three-Dimensional Structure−Activity Relationships of Nonsteroidal Ligands in Complex with Androgen Receptor Ligand-Binding Domain
Annu A. Söderholm, Pekka T. Lehtovuori, and Tommi H. Nyrönen
pp 917–925Publication Date (Web): January 26, 2005 (Article)
DOI: 10.1021/jm0495879
Design, Synthesis, and Biological Evaluation of Novel Potent and Selective αvβ3/αvβ5 Integrin Dual Inhibitors with Improved Bioavailability. Selection of the Molecular Core
Juan José Marugán, Carl Manthey, Beth Anaclerio, Lou Lafrance, Tianbao Lu, Tom Markotan, Kristi A. Leonard, Carl Crysler, Stephen Eisennagel, Malini Dasgupta, and Bruce Tomczuk
pp 926–934Publication Date (Web): January 28, 2005 (Article)
DOI: 10.1021/jm049725u
Multivariate Design, Synthesis, and Biological Evaluation of Peptide Inhibitors of FimC/FimH Protein−Protein Interactions in Uropathogenic Escherichia coli
Andreas Larsson, Susanne M. C. Johansson, Jerome S. Pinkner, Scott J. Hultgren, Fredrik Almqvist, Jan Kihlberg, and Anna Linusson
pp 935–945Publication Date (Web): February 01, 2005 (Article)
DOI: 10.1021/jm040818l
Application of a Flexible Synthesis of (5R)-Thiolactomycin To Develop New Inhibitors of Type I Fatty Acid Synthase
Jill M. McFadden, Susan M. Medghalchi, Jagan N. Thupari, Michael L. Pinn, Aravinda Vadlamudi, Katherine I. Miller, Francis P. Kuhajda, and Craig A. Townsend
pp 946–961Publication Date (Web): January 20, 2005 (Article)
DOI: 10.1021/jm049389h
Comparison of Automated Docking Programs as Virtual Screening Tools
Maxwell D. Cummings, Renee L. DesJarlais, Alan C. Gibbs, Venkatraman Mohan, and Edward P. Jaeger
pp 962–976Publication Date (Web): January 20, 2005 (Article)
DOI: 10.1021/jm049798d
Mechanism of Cytotoxicity of Copper(I) Complexes of 1,2-Bis(diphenylphosphino)ethane
Nusrat J. Sanghamitra, Pornima Phatak, Sanjeev Das, Ashoka G. Samuelson, and Kumaravel Somasundaram
pp 977–985Publication Date (Web): January 29, 2005 (Article)
DOI: 10.1021/jm049430g
Novel Anticholinesterases Based on the Molecular Skeletons of Furobenzofuran and Methanobenzodioxepine
Weiming Luo, Qian-sheng Yu, Ming Zhan, Damon Parrish, Jeffrey R. Deschamps, Santosh S. Kulkarni, Harold W. Holloway, George M. Alley, Debomoy K. Lahiri, Arnold Brossi, and Nigel H. Greig
pp 986–994Publication Date (Web): January 12, 2005 (Article)
DOI: 10.1021/jm049309+
Full Text HTMLCoMFA, Synthesis, and Pharmacological Evaluation of (E)-3-(2-Carboxy-2-arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic Acids: 3-[2-(3-Aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic Acid, a Potent Selective Glycine-Site NMDA Receptor Antagonist
Bruce M. Baron, Robert J. Cregge, Robert A. Farr, Dirk Friedrich, Raymond S. Gross, Boyd L. Harrison, David A. Janowick, Donald Matthews, Timothy C. McCloskey, Scott Meikrantz, Philip L. Nyce, Roy Vaz, and William A. Metz
pp 995–1018Publication Date (Web): February 01, 2005 (Article)
DOI: 10.1021/jm0491849
Novel Inhibitors of Human Histone Deacetylases: Design, Synthesis, Enzyme Inhibition, and Cancer Cell Growth Inhibition of SAHA-Based Non-hydroxamates
Takayoshi Suzuki, Yuki Nagano, Akiyasu Kouketsu, Azusa Matsuura, Sakiko Maruyama, Mineko Kurotaki, Hidehiko Nakagawa, and Naoki Miyata
pp 1019–1032Publication Date (Web): January 25, 2005 (Article)
DOI: 10.1021/jm049207j
Synthesis and Cellular Studies of Nonaggregated Water-Soluble Phthalocyanines
Wei Liu, Timothy J. Jensen, Frank R. Fronczek, Robert P. Hammer, Kevin M. Smith, and M. Graça H. Vicente
pp 1033–1041Publication Date (Web): January 27, 2005 (Article)
DOI: 10.1021/jm049375b
The Role of Intracellularly Released Formaldehyde and Butyric Acid in the Anticancer Activity of Acyloxyalkyl Esters
Abraham Nudelman, Inesa Levovich, Suzanne M. Cutts, Don R. Phillips, and Ada Rephaeli
pp 1042–1054Publication Date (Web): January 22, 2005 (Article)
DOI: 10.1021/jm049428p
Optimization and Validation of a Docking-Scoring Protocol; Application to Virtual Screening for COX-2 Inhibitors
Jean-Christophe Mozziconacci, Eric Arnoult, Philippe Bernard, Quoc Tuan Do, Christophe Marot, and Luc Morin-Allory
pp 1055–1068Publication Date (Web): February 01, 2005 (Article)
DOI: 10.1021/jm049332v
A New Method for Estimating the Importance of Hydrophobic Groups in the Binding Site of a Protein
Matthew D. Kelly and Ricardo L. Mancera
pp 1069–1078Publication Date (Web): January 15, 2005 (Article)
DOI: 10.1021/jm049524q
Extravascular Transport of Drugs in Tumor Tissue: Effect of Lipophilicity on Diffusion of Tirapazamine Analogues in Multicellular Layer Cultures
Frederik B. Pruijn, Joanna R. Sturman, H. D. Sarath Liyanage, Kevin O. Hicks, Michael P. Hay, and William R. Wilson
pp 1079–1087Publication Date (Web): January 27, 2005 (Article)
DOI: 10.1021/jm049549p
Structure-based Drug Discovery Using GPCR Homology Modeling: Successful Virtual Screening for Antagonists of the Alpha1A Adrenergic Receptor
Andreas Evers and Thomas Klabunde
pp 1088–1097Publication Date (Web): February 03, 2005 (Article)
DOI: 10.1021/jm0491804
Synthesis and Biological Evaluation of Dimeric RGD Peptide−Paclitaxel Conjugate as a Model for Integrin-Targeted Drug Delivery
Xiaoyuan Chen, Carmen Plasencia, Yingping Hou, and Nouri Neamati
pp 1098–1106Publication Date (Web): January 27, 2005 (Article)
DOI: 10.1021/jm049165z
Optimization of 6,7-Disubstituted-4-(arylamino)quinoline-3-carbonitriles as Orally Active, Irreversible Inhibitors of Human Epidermal Growth Factor Receptor-2 Kinase Activity
Hwei-Ru Tsou, Elsebe G. Overbeek-Klumpers, William A. Hallett, Marvin F. Reich, M. Brawner Floyd, Bernard D. Johnson, Ronald S. Michalak, Ramaswamy Nilakantan, Carolyn Discafani, Jonathan Golas, Sridhar K. Rabindran, Ru Shen, Xiaoqing Shi, Yu-Fen Wang, Janis Upeslacis, and Allan Wissner
pp 1107–1131Publication Date (Web): January 27, 2005 (Article)
DOI: 10.1021/jm040159c
Indazole Estrogens: Highly Selective Ligands for the Estrogen Receptor β
Meri De Angelis, Fabio Stossi, Kathryn A. Carlson, Benita S. Katzenellenbogen, and John A. Katzenellenbogen
pp 1132–1144Publication Date (Web): January 21, 2005 (Article)
DOI: 10.1021/jm049223g
Synthesis and Biological Evaluation of a New Series of 2,3,5-Substituted [1,2,4]-Thiadiazoles as Modulators of Adenosine A1 Receptors and Their Molecular Mechanism of Action
Anikó Göblyös, Henk de Vries, Johannes Brussee, and Adriaan P. IJzerman
pp 1145–1151Publication Date (Web): January 25, 2005 (Article)
DOI: 10.1021/jm049337s
Synthesis and Cytotoxic Evaluation of Novel Spirohydantoin Derivatives of the Dihydrothieno[2,3-b]naphtho-4,9-dione System
Isabel Gomez-Monterrey, Giovanni Santelli, Pietro Campiglia, Daniela Califano, Fabiano Falasconi, Claudio Pisano, Loredana Vesci, Teresa Lama, Paolo Grieco, and Ettore Novellino
pp 1152–1157Publication Date (Web): January 22, 2005 (Article)
DOI: 10.1021/jm0408565
Novel [2‘,5‘-Bis-O-(tert-butyldimethylsilyl)-β-d-ribofuranosyl]- 3‘-spiro-5‘ ‘-(4‘ ‘-amino-1‘ ‘,2‘ ‘-oxathiole-2‘ ‘,2‘ ‘-dioxide) Derivatives with Anti-HIV-1 and Anti-Human-Cytomegalovirus Activity
Sonia de Castro, Esther Lobatón, María-Jesús Pérez-Pérez, Ana San-Félix, Alessandra Cordeiro, Graciela Andrei, Robert Snoeck, Erik De Clercq, Jan Balzarini, María-José Camarasa, and Sonsoles Velázquez
pp 1158–1168Publication Date (Web): January 21, 2005 (Article)
DOI: 10.1021/jm040868q
3-[(2R)-Amino-2-phenylethyl]-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)- 6-methylpyrimidin-2,4-dione (NBI 42902) as a Potent and Orally Active Antagonist of the Human Gonadotropin-Releasing Hormone Receptor. Design, Synthesis, and in Vitro and in Vivo Characterization
Fabio C. Tucci, Yun-Fei Zhu, R. Scott Struthers, Zhiqiang Guo, Timothy D. Gross, Martin W. Rowbottom, Oscar Acevedo, Yinghong Gao, John Saunders, Qiu Xie, Greg J. Reinhart, Xin-Jun Liu, Nicholas Ling, Anne K. L. Bonneville, Takung Chen, Haig Bozigian, and Chen Chen
pp 1169–1178Publication Date (Web): January 25, 2005 (Article)
DOI: 10.1021/jm049218c
Modulation of MRP-1-Mediated Multidrug Resistance by Indomethacin Analogues
Claudia Rosenbaum, Sonja Röhrs, Oliver Müller, and Herbert Waldmann
pp 1179–1187Publication Date (Web): January 25, 2005 (Article)
DOI: 10.1021/jm0499099
Synthesis and Biological Evaluation of Neutral and Zwitterionic 3-Carboranyl Thymidine Analogues for Boron Neutron Capture Therapy
Youngjoo Byun, Junhua Yan, Ashraf S. Al-Madhoun, Jayaseharan Johnsamuel, Weilian Yang, Rolf F. Barth, Staffan Eriksson, and Werner Tjarks
pp 1188–1198Publication Date (Web): January 27, 2005 (Article)
DOI: 10.1021/jm0491896
Synthesis and Evaluation of S-Acyl-2-thioethyl Esters of Modified Nucleoside 5‘-Monophosphates as Inhibitors of Hepatitis C Virus RNA Replication
Thazha P. Prakash, Marija Prhavc, Anne B. Eldrup, P. Dan Cook, Steven S. Carroll, David B. Olsen, Mark W. Stahlhut, Joanne E. Tomassini, Malcolm MacCoss, Sheila M. Galloway, Catherine Hilliard, and Balkrishen Bhat
pp 1199–1210Publication Date (Web): February 01, 2005 (Article)
DOI: 10.1021/jm0495172
Synthesis and Evaluation of Double-Prodrugs against HIV. Conjugation of D4T with 6-Benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, Emivirine)-Type Reverse Transcriptase Inhibitors via the SATE Prodrug Approach
Lene Petersen, Per T. Jørgensen, Claus Nielsen, Thomas H. Hansen, John Nielsen, and Erik B. Pedersen
pp 1211–1220Publication Date (Web): January 22, 2005 (Article)
DOI: 10.1021/jm040845b
Synthesis, Nicotinic Acetylcholine Receptor Binding, and Antinociceptive Properties of 3‘-Substituted Deschloroepibatidine Analogues. Novel Nicotinic Antagonists
F. Ivy Carroll, Wei Ma, Yasuno Yokota, Jeffrey R. Lee, Lawrence E. Brieaddy, Hernán A. Navarro, M. I. Damaj, and Billy R. Martin
pp 1221–1228Publication Date (Web): February 01, 2005 (Article)
DOI: 10.1021/jm040160b
Chiral DNA Gyrase Inhibitors. 3. Probing the Chiral Preference of the Active Site of DNA Gyrase. Synthesis of 10-Fluoro-6-methyl-6,7-dihydro-9-piperazinyl- 2H-benzo[a]quinolizin-20-one-3-carboxylic Acid Analogues
Robert A. Fecik, Pratik Devasthale, Segaran Pillai, Ali Keschavarz-Shokri, Linus Shen, and Lester A. Mitscher
pp 1229–1236Publication Date (Web): January 26, 2005 (Article)
DOI: 10.1021/jm0401356
8-Substituted Analogues of 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl- adenine: Highly Potent and Selective PDE4 Inhibitors
John W. F. Whitehead, Gary P. Lee, Parviz Gharagozloo, Peter Hofer, André Gehrig, Peter Wintergerst, Donald Smyth, William McCoull, Mohamed Hachicha, Aniket Patel, and Donald J. Kyle
pp 1237–1243Publication Date (Web): January 27, 2005 (Article)
DOI: 10.1021/jm030603w
Degradation, Insulin Secretion, and Antihyperglycemic Actions of Two Palmitate-Derivitized N-Terminal Pyroglutamyl Analogues of Glucose-Dependent Insulinotropic Polypeptide
Nigel Irwin, Brian D. Green, Victor A. Gault, Brett Greer, Patrick Harriott, Clifford J. Bailey, Peter R. Flatt, and Finbarr P. M. O'Harte
pp 1244–1250Publication Date (Web): February 01, 2005 (Article)
DOI: 10.1021/jm049262s
Brief Articles
Synthesis of (±)-2-O-[4‘-(N-9‘ ‘-Purinyl)butyl] myo-Inositol 1,4,5-Tris(phosphate), a Potent Full Agonist at the d-myo-Inositol 1,4,5-Tris(phosphate) Receptor
Marc-Antoine Moris, Annabelle Z. Caron, Gaétan Guillemette, Didier Rognan, Martine Schmitt, and Gilbert Schlewer
pp 1251–1255Publication Date (Web): January 27, 2005 (Brief Article)
DOI: 10.1021/jm049458s
Antiviral Activity of Glycyrrhizic Acid Derivatives against SARS−Coronavirus
Gerold Hoever, Lidia Baltina, Martin Michaelis, Rimma Kondratenko, Lia Baltina, Genrich A. Tolstikov, Hans W. Doerr, and Jindrich Cinatl, Jr.
pp 1256–1259Publication Date (Web): January 19, 2005 (Brief Article)
DOI: 10.1021/jm0493008
New Potential Antihistaminic Compounds. Virtual Combinatorial Chemistry, Computational Screening, Real Synthesis, and Pharmacological Evaluation
María J. Duart, Gerardo M. Antón-Fos, Pedro A. Alemán, Joan B. Gay-Roig, María E. González-Rosende, Jorge Gálvez, and Ramón García-Domenech
pp 1260–1264Publication Date (Web): January 29, 2005 (Brief Article)
DOI: 10.1021/jm040877z
Identification from a Positional Scanning Peptoid Library of in Vivo Active Compounds That Neutralize Bacterial Endotoxins
Puig Mora, Isabel Masip, Nuria Cortés, Regina Marquina, Ramón Merino, Jesús Merino, Teresa Carbonell, Ismael Mingarro, Angel Messeguer, and Enrique Pérez-Payá
pp 1265–1268Publication Date (Web): February 02, 2005 (Brief Article)
DOI: 10.1021/jm040834i
Antithrombin Activation by Nonsulfated, Non-Polysaccharide Organic Polymer
Bernhard H. Monien and Umesh R. Desai
pp 1269–1273Publication Date (Web): January 27, 2005 (Brief Article)
DOI: 10.1021/jm0492960
Amino Acid Ester Prodrugs of the Antiviral Agent 2-Bromo-5,6-dichloro-1-(β-d-ribofuranosyl)benzimidazole as Potential Substrates of hPEPT1 Transporter
Xueqin Song, Balvinder S. Vig, Philip L. Lorenzi, John C. Drach, Leroy B. Townsend, and Gordon L. Amidon
pp 1274–1277Publication Date (Web): February 01, 2005 (Brief Article)
DOI: 10.1021/jm049450i
CH···O and CH···N Hydrogen Bonds in Ligand Design: A Novel Quinazolin-4-ylthiazol-2-ylamine Protein Kinase Inhibitor
Albert C. Pierce, Ernst ter Haar, Hayley M. Binch, David P. Kay, Sanjay R. Patel, and Pan Li
pp 1278–1281Publication Date (Web): January 25, 2005 (Brief Article)
DOI: 10.1021/jm0492249
Novel 2-Alkylamino-1,4-benzoxazine Derivatives as Potent Neuroprotective Agents: Structure−Activity Relationship Studies
Estelle Blattes, Brian Lockhart, Pierre Lestage, Leslie Schwendimann, Pierre Gressens, Maurice-Bernard Fleury, and Martine Largeron
pp 1282–1286Publication Date (Web): January 25, 2005 (Brief Article)
DOI: 10.1021/jm040874m
Greater Than the Sum of Its Parts: Combining Models for Useful ADMET Prediction
Sean E. O'Brien and Marcel J. de Groot
pp 1287–1291Publication Date (Web): February 01, 2005 (Brief Article)
DOI: 10.1021/jm049254b
Synthesis, Antitumor Evaluation, and Apoptosis-Inducing Activity of Hydroxylated (E)-Stilbenes
Cedric J. Lion, Charles S. Matthews, Malcolm F. G. Stevens, and Andrew D. Westwell
pp 1292–1295Publication Date (Web): February 02, 2005 (Brief Article)
DOI: 10.1021/jm049238e
Book Reviews
Synthetic Multivalent Molecules: Concepts and Biomedical Applications By Seok-Ki Choi. Wiley-Interscience, Hoboken, NJ. 2004. xxvi + 418 pp. 16 × 24 cm. ISBN 0471563471. $99.95.
Jan W. F. Wasley
p 1296Publication Date (Web): January 29, 2005 (Book Review)
DOI: 10.1021/jm040212x
Introduction to Enzyme and Coenzyme Chemistry. Second Edition By T. D. H. Bugg. Blackwell Publishing, Oxford, U.K. x + 304 pp. 17.5 × 24 cm. ISBN 1-4051-1452-5. $75.00.
D. Eric Walters
p 1296Publication Date (Web): February 01, 2005 (Book Review)
DOI: 10.1021/jm040218m