Table of Contents
December 1, 2005
Volume 48, Issue 24
Pages 7503-7917
About the Cover: Illustration of the binding mode of a biheteroaryl inhibitor to vascular endothelial growth factor receptor-2 (Kuo, G.-H.; et al. J. Med. Chem. 2005, 48, 1886-1900).
Perspective
Heat Shock Protein 90 Inhibitors. A Text Book Example of Medicinal Chemistry?
Yves L. Janin
pp 7503–7512Publication Date (Web): November 08, 2005 (Perspective)
DOI: 10.1021/jm050759r
Hi-Res PDF Letters
Rhodamine-Labeled 2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane Analogues as High-Affinity Fluorescent Probes for the Dopamine Transporter
Joo Hwan Cha, Mu-Fa Zou, Erika M. Adkins, Søren G. F. Rasmussen, Claus Juul Loland, Bernhard Schoenenberger, Ulrik Gether, and Amy Hauck Newman
pp 7513–7516Publication Date (Web): November 05, 2005 (Letter)
DOI: 10.1021/jm050431y
Discovery of a Potent, Orally Available, and Isoform-Selective Retinoic Acid β2 Receptor Agonist
Birgitte W. Lund, Fabrice Piu, Natalie K. Gauthier, Anne Eeg, Erika Currier, Vladimir Sherbukhin, Mark R. Brann, Uli Hacksell, and Roger Olsson
pp 7517–7519Publication Date (Web): November 04, 2005 (Letter)
DOI: 10.1021/jm050891r
Articles
Design and Synthesis of Tri-Ring P3 Benzamide-Containing Aminonitriles as Potent, Selective, Orally Effective Inhibitors of Cathepsin K
James T. Palmer, Clifford Bryant, Dan-Xiong Wang, Dana E. Davis, Eduardo L. Setti, Robert M. Rydzewski, Shankar Venkatraman, Zong-Qiang Tian, Leland C. Burrill, Rohan V. Mendonca, Eric Springman, John McCarter, Tobee Chung, Harry Cheung, James W. Janc, Mary McGrath, John R. Somoza, Philip Enriquez, Z. Walter Yu, Robert M. Strickley, Liang Liu, Michael C. Venuti, M. David Percival, Jean-Pierre Falgueyret, Peppi Prasit, Renata Oballa, Denis Riendeau, Robert N. Young, Gregg Wesolowski, Sevgi B. Rodan, Colena Johnson, Donald B. Kimmel, and Gideon Rodan
pp 7520–7534Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm058198r
Lysosomotropism of Basic Cathepsin K Inhibitors Contributes to Increased Cellular Potencies against Off-Target Cathepsins and Reduced Functional Selectivity
Jean-Pierre Falgueyret, Sylvie Desmarais, Renata Oballa, W. Cameron Black, Wanda Cromlish, Karine Khougaz, Sonia Lamontagne, Frederic Massé, Denis Riendeau, Sylvie Toulmond, and M. David Percival
pp 7535–7543Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm0504961
Combining in Silico Tools and NMR Data To Validate Protein−Ligand Structural Models: Application to Matrix Metalloproteinases
Ivano Bertini, Marco Fragai, Andrea Giachetti, Claudio Luchinat, Massimiliano Maletta, Giacomo Parigi, and Kwon Joo Yeo
pp 7544–7559Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050574k
2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as Covalent-Binding, Irreversible Inhibitors of the Kinase Domain of Vascular Endothelial Growth Factor Receptor-2
Allan Wissner, M. Brawner Floyd, Bernard D. Johnson, Heidi Fraser, Charles Ingalls, Thomas Nittoli, Russell G. Dushin, Carolyn Discafani, Ramaswamy Nilakantan, Joseph Marini, Malini Ravi, Kinwang Cheung, Xingzhi Tan, Sylvia Musto, Tami Annable, Marshall M. Siegel, and Frank Loganzo
pp 7560–7581Publication Date (Web): November 03, 2005 (Article)
DOI: 10.1021/jm050559f
Crystal Structures for HIV-1 Reverse Transcriptase in Complexes with Three Pyridinone Derivatives: A New Class of Non-Nucleoside Inhibitors Effective against a Broad Range of Drug-Resistant Strains
Daniel M. Himmel, Kalyan Das, Arthur D. Clark, Jr., Stephen H. Hughes, Abdellah Benjahad, Said Oumouch, Jérôme Guillemont, Sophie Coupa, Alain Poncelet, Imre Csoka, Christophe Meyer, Koen Andries, Chi Hung Nguyen, David S. Grierson, and Eddy Arnold
pp 7582–7591Publication Date (Web): November 02, 2005 (Article)
DOI: 10.1021/jm0500323
3,6-Disubstituted Coumarins as Mechanism-Based Inhibitors of Thrombin and Factor Xa
Raphaël Frédérick, Séverine Robert, Caroline Charlier, Jérôme de Ruyck, Johan Wouters, Bernard Pirotte, Bernard Masereel, and Lionel Pochet
pp 7592–7603Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050448g
Structural Basis of Inhibitor Specificity of the Human Protooncogene Proviral Insertion Site in Moloney Murine Leukemia Virus (PIM-1) Kinase
Alex N. Bullock, Judit É. Debreczeni, Oleg Y. Fedorov, Adam Nelson, Brian D. Marsden, and Stefan Knapp
pp 7604–7614Publication Date (Web): October 27, 2005 (Article)
DOI: 10.1021/jm0504858
Pharmacophoric Features of Biguanide Derivatives: An Electronic and Structural Analysis
Prasad V. Bharatam, Dhilon S. Patel, and Pansy Iqbal
pp 7615–7622Publication Date (Web): November 03, 2005 (Article)
DOI: 10.1021/jm050602z
Preorganization of the Hydroxyethylene Dipeptide Isostere: The Preferred Conformation in Solution Resembles the Conformation Bound to BACE
Paloma Vidal, David Timm, Howard Broughton, Shu-Hui Chen, José A. Martín, Alfonso Rivera-Sagredo, James R. McCarthy, Michael J. Shapiro, and Juan F. Espinosa
pp 7623–7627Publication Date (Web): November 02, 2005 (Article)
DOI: 10.1021/jm050631+
Full Text HTMLIdentification of the Structural Requirements of the Receptor-Binding Affinity of Diphenolic Azoles to Estrogen Receptors α and β by Three-Dimensional Quantitative Structure−Activity Relationship and Structure−Activity Relationship Analysis
Assia Demyttenaere-Kovatcheva, Mark T. D. Cronin, Emilio Benfenati, Alessandra Roncaglioni, and Elena LoPiparo
pp 7628–7636Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050604j
N-Benzylisatin Sulfonamide Analogues as Potent Caspase-3 Inhibitors: Synthesis, in Vitro Activity, and Molecular Modeling Studies
Wenhua Chu, Jun Zhang, Chenbo Zeng, Justin Rothfuss, Zhude Tu, Yunxiang Chu, David E. Reichert, Michael J. Welch, and Robert H. Mach
pp 7637–7647Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm0506625
Doxazolidine, a Proposed Active Metabolite of Doxorubicin That Cross-links DNA
Glen C. Post, Benjamin L. Barthel, David J. Burkhart, John R. Hagadorn, and Tad H. Koch
pp 7648–7657Publication Date (Web): November 04, 2005 (Article)
DOI: 10.1021/jm050678v
Design, Synthesis, and Microbiological Evaluation of New Candida albicans CYP51 Inhibitors
Fausto Schiaffella, Antonio Macchiarulo, Lara Milanese, Anna Vecchiarelli, Gabriele Costantino, Donatella Pietrella, and Renata Fringuelli
pp 7658–7666Publication Date (Web): November 01, 2005 (Article)
DOI: 10.1021/jm050685j
Conformationally Constrained CCK4 Analogues Incorporating IBTM and BTD β-Turn Mimetics
Mercedes Martín-Martínez, Natalia De la Figuera, Miriam LaTorre, M. Teresa García-López, Edurne Cenarruzabeitia, Joaquín Del Río, and Rosario González-Muñiz
pp 7667–7674Publication Date (Web): November 02, 2005 (Article)
DOI: 10.1021/jm050689o
Grafting Aminocyclopentane Carboxylic Acids onto the RGD Tripeptide Sequence Generates Low Nanomolar αVβ3/αVβ5 Integrin Dual Binders
Giovanni Casiraghi, Gloria Rassu, Luciana Auzzas, Paola Burreddu, Enrico Gaetani, Lucia Battistini, Franca Zanardi, Claudio Curti, Giuseppe Nicastro, Laura Belvisi, Ilaria Motto, Massimo Castorina, Giuseppe Giannini, and Claudio Pisano
pp 7675–7687Publication Date (Web): November 04, 2005 (Article)
DOI: 10.1021/jm050698x
Interaction of Papain-like Cysteine Proteases with Dipeptide-Derived Nitriles
Reik Löser, Klaus Schilling, Elke Dimmig, and Michael Gütschow
pp 7688–7707Publication Date (Web): November 03, 2005 (Article)
DOI: 10.1021/jm050686b
Mono- or Diphenylpyridazines Connected to N-(2,4-Difluorophenyl)-N‘-heptylurea as Acyl-CoA:Cholesterol Acyltransferase Inhibitors
Arianna Gelain, Ilaria Bettinelli, Daniela Barlocco, Byoung-Mog Kwon, Tae-Sook Jeong, Kyung-Hyun Cho, and Lucio Toma
pp 7708–7713Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050703x
Binding of the Anticancer Prodrug CB1954 to the Activating Enzyme NQO2 Revealed by the Crystal Structure of Their Complex
Majed AbuKhader, John Heap, Cristina De Matteis, Barrie Kellam, Stephen W. Doughty, Nigel Minton, and Massimo Paoli
pp 7714–7719Publication Date (Web): November 02, 2005 (Article)
DOI: 10.1021/jm050730n
Syntheses, Biological Evaluation, and Molecular Modeling of 18F-Labeled 4-Anilidopiperidines as μ-Opioid Receptor Imaging Agents
Gjermund Henriksen, Stefan Platzer, János Marton, Andrea Hauser, Achim Berthele, Markus Schwaiger, Luciana Marinelli, Antonio Lavecchia, Ettore Novellino, and Hans-Jürgen Wester
pp 7720–7732Publication Date (Web): November 03, 2005 (Article)
DOI: 10.1021/jm0507274
Novel Lavendamycin Analogues as Antitumor Agents: Synthesis, in Vitro Cytotoxicity, Structure−Metabolism, and Computational Molecular Modeling Studies with NAD(P)H:Quinone Oxidoreductase 1
Mary Hassani, Wen Cai, David C. Holley, Jayana P. Lineswala, Babu R. Maharjan, G. Reza Ebrahimian, Hassan Seradj, Mark G. Stocksdale, Farahnaz Mohammadi, Christopher C. Marvin, John M. Gerdes, Howard D. Beall, and Mohammad Behforouz
pp 7733–7749Publication Date (Web): November 08, 2005 (Article)
DOI: 10.1021/jm050758z
Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 8.1 {2-[2-(4-Chlorobenzyloxy)phenoxy]ethyl}-[2-(2,6-dimethoxyphenoxy)ethyl]amine (Clopenphendioxan) as a Tool to Highlight the Involvement of α1D- and α1B-Adrenoreceptor Subtypes in the Regulation of Human PC-3 Prostate Cancer Cell Apoptosis and Proliferation
Wilma Quaglia, Giorgio Santoni, Maria Pigini, Alessandro Piergentili, Francesco Gentili, Michela Buccioni, Michela Mosca, Roberta Lucciarini, Consuelo Amantini, Massimo Ivan Nabissi, Patrizia Ballarini, Elena Poggesi, Amedeo Leonardi, and Mario Giannella
pp 7750–7763Publication Date (Web): November 02, 2005 (Article)
DOI: 10.1021/jm0580398
Docking Studies and Ligand Recognition in Folylpolyglutamate Synthetase
Xiao-Jian Tan and Heather A. Carlson
pp 7764–7772Publication Date (Web): November 01, 2005 (Article)
DOI: 10.1021/jm0507734
Conformationally Sampled Pharmacophore for Peptidic δ Opioid Ligands
Denzil Bernard, Andrew Coop, and Alexander D. MacKerell Jr.
pp 7773–7780Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm050785p
Small Molecule Inhibitors of Dynamin I GTPase Activity: Development of Dimeric Tyrphostins
Timothy Hill, Luke R. Odell, Jennifer K. Edwards, Mark E. Graham, Andrew B. McGeachie, Jenny Rusak, Annie Quan, Ruben Abagyan, Janet L. Scott, Phillip J. Robinson, and Adam McCluskey
pp 7781–7788Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm040208l
Design, Synthesis, and Biological Evaluation of Sirtinol Analogues as Class III Histone/Protein Deacetylase (Sirtuin) Inhibitors
Antonello Mai, Silvio Massa, Siva Lavu, Riccardo Pezzi, Silvia Simeoni, Rino Ragno, Francesca R. Mariotti, Francesco Chiani, Giorgio Camilloni, and David A. Sinclair
pp 7789–7795Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm050100l
Evaluating the Molecular Mechanics Poisson−Boltzmann Surface Area Free Energy Method Using a Congeneric Series of Ligands to p38 MAP Kinase
David A. Pearlman
pp 7796–7807Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050306m
Adenosine Kinase Inhibitors. 6. Synthesis, Water Solubility, and Antinociceptive Activity of 5-Phenyl-7-(5-deoxy-β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidines Substituted at C4 with Glycinamides and Related Compounds
Brett C. Bookser, Bheemarao G. Ugarkar, Michael C. Matelich, Robert H. Lemus, Matthew Allan, Megumi Tsuchiya, Masami Nakane, Atsushi Nagahisa, James B. Wiesner, and Mark D. Erion
pp 7808–7820Publication Date (Web): November 03, 2005 (Article)
DOI: 10.1021/jm050394a
Platinum-Based Antitumor Drugs Containing Enantiomerically Pure α-Trifluoromethyl Alanine as Ligand
Nicola Margiotta, Paride Papadia, Francesco Lazzaro, Marcello Crucianelli, Francesco De Angelis, Claudio Pisano, Loredana Vesci, and Giovanni Natile
pp 7821–7828Publication Date (Web): November 01, 2005 (Article)
DOI: 10.1021/jm0504003
Discovery of Potent Chromen-4-one Inhibitors of the DNA-Dependent Protein Kinase (DNA-PK) Using a Small-Molecule Library Approach
Ian R. Hardcastle, Xiaoling Cockcroft, Nicola J. Curtin, Marine Desage El-Murr, Justin J. J. Leahy, Martin Stockley, Bernard T. Golding, Laurent Rigoreau, Caroline Richardson, Graeme C. M. Smith, and Roger J. Griffin
pp 7829–7846Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm050444b
On the Use of Nonfluorescent Dye Labeled Ligands in FRET-Based Receptor Binding Studies
Chouaib Tahtaoui, Fabrice Guillier, Philippe Klotz, Jean-Luc Galzi, Marcel Hibert, and Brigitte Ilien
pp 7847–7859Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050459+
Carbonic Anhydrase Inhibitors. The Mitochondrial Isozyme VB as a New Target for Sulfonamide and Sulfamate Inhibitors
Isao Nishimori, Daniela Vullo, Alessio Innocenti, Andrea Scozzafava, Antonio Mastrolorenzo, and Claudiu T. Supuran
pp 7860–7866Publication Date (Web): October 29, 2005 (Article)
DOI: 10.1021/jm050483n
Synthesis and Pharmacology of Willardiine Derivatives Acting as Antagonists of Kainate Receptors
Nigel P. Dolman, Helen M. Troop, Julia C. A. More, Andrew Alt, Jody L. Knauss, Robert Nistico, Samantha Jack, Richard M. Morley, Zuner A. Bortolotto, Peter J. Roberts, David Bleakman, Graham L. Collingridge, and David E. Jane
pp 7867–7881Publication Date (Web): November 05, 2005 (Article)
DOI: 10.1021/jm050584l
Discovery and Development of a New Class of Potent, Selective, Orally Active Oxytocin Receptor Antagonists
Anna Quattropani, Jérôme Dorbais, David Covini, Pierre-André Pittet, Véronique Colovray, Russell J. Thomas, Richard Coxhead, Serge Halazy, Alexander Scheer, Marc Missotten, Guidon Ayala, Charles Bradshaw, Anne-Marie De Raemy-Schenk, Anthony Nichols, Rocco Cirillo, Enrico Gillio Tos, Claudio Giachetti, Lucia Golzio, Paolo Marinelli, Dennis J. Church, Claude Barberis, André Chollet, and Matthias K. Schwarz
pp 7882–7905Publication Date (Web): November 01, 2005 (Article)
DOI: 10.1021/jm050645f
Brief Articles
Design, Synthesis, and Biological Evaluation of Hybrid Molecules Containing α-Methylene-γ-Butyrolactones and α-Bromoacryloyl Moieties
Romeo Romagnoli, Pier Giovanni Baraldi, Mojgan Aghazadeh Tabrizi, Jaime Bermejo, Francisco Estévez, Monica Borgatti, and Roberto Gambari
pp 7906–7910Publication Date (Web): October 29, 2005 (Brief Article)
DOI: 10.1021/jm058012o
Structure of a Synthetic Fragment of the Lipopolysaccharide (LPS) Binding Protein When Bound to LPS and Design of a Peptidic LPS Inhibitor
Primož Pristovšek, Saša Simčič, Branka Wraber, and Uroš Urleb
pp 7911–7914Publication Date (Web): November 01, 2005 (Brief Article)
DOI: 10.1021/jm050762a
Book Reviews
Progress in Medicinal Chemistry. Volume 43 Edited by F. D. King and G. Lawton. Elsevier B.V., Amsterdam, The Netherlands. 2005. x + 289 pp. 14.5 × 22 cm. ISBN 0 444 51572 0. $159.00.
Jonathan L. Vennerstrom
pp 7915–7916Publication Date (Web): October 29, 2005 (Book Review)
DOI: 10.1021/jm0582726
Microwaves in Organic and Medicinal Chemistry By C. Oliver Kappe and Alexander Stadler. (Volume 25 of Methods and Principles in Medicinal Chemistry. Edited by R. Mannhold, H. Kubinyi, and G. Folkers.) Wiley VCH, Weinheim, Germany. 2005. xii + 409 pp. 17.5 × 24.5 cm. ISBN -527-31210-2. $170.00.
Thomas J. Caggiano
p 7915Publication Date (Web): October 27, 2005 (Book Review)
DOI: 10.1021/jm058273y
Advances in Organic Chemistry. Volume 1 Edited by Atta-ur-Rahman and Gerhard Jenner. Bentham Science Publishers, Hilversum, The Netherlands. 2005. vi + 568 pp. 17.5 × 25 cm. ISBN 90-77527-02-8. $130.00.
Michael B. Jarstfer
p 7916Publication Date (Web): November 08, 2005 (Book Review)
DOI: 10.1021/jm0582773
Additions and Corrections
A Common Pharmacophore for a Diverse Set of Colchicine Site Inhibitors Using a Structure-Based Approach.
Tam Luong Nguyen, Connor McGrath, Ann R. Hermone, James C. Burnett, Daniel W. Zaharevitz, Billy W. Day, Peter Wipf, Ernest Hamel, and Rick Gussio:
p 7917Publication Date (Web): November 01, 2005 (Addition/Correction)
DOI: 10.1021/jm058275i