Table of Contents
August 11, 2005
Volume 48, Issue 16
Pages 5059-5382
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
The Endocannabinoid System: Drug Targets, Lead Compounds, and Potential Therapeutic Applications
Didier M. Lambert and Christopher J. Fowler
pp 5059–5087Publication Date (Web): July 19, 2005 (Perspective)
DOI: 10.1021/jm058183t
Hi-Res PDF Letters
Design and Synthesis of Depeptidized Macrocyclic Inhibitors of Hepatitis C NS3-4A Protease Using Structure-Based Drug Design
Srikanth Venkatraman, F. George Njoroge, Viyyoor M. Girijavallabhan, Vincent S. Madison, Nanua H. Yao, Andrew J. Prongay, Nancy Butkiewicz, and John Pichardo
pp 5088–5091Publication Date (Web): July 14, 2005 (Letter)
DOI: 10.1021/jm0489556
Synthesis and Structure−Activity Relationship of Novel 6-Aryl-1,4- dihydrobenzo[d][1,3]oxazine-2-thiones as Progesterone Receptor Modulators Leading to the Potent and Selective Nonsteroidal Progesterone Receptor Agonist Tanaproget
Andrew Fensome, Reinhold Bender, Rajiv Chopra, Jeff Cohen, Mark A. Collins, Valerie Hudak, Karl Malakian, Susan Lockhead, Andrea Olland, Kristine Svenson, Eugene A. Terefenko, Ray J. Unwalla, James M. Wilhelm, Scott Wolfrom, Yuan Zhu, Zhiming Zhang, Puwen Zhang, Richard C. Winneker, and Jay Wrobel
pp 5092–5095Publication Date (Web): July 12, 2005 (Letter)
DOI: 10.1021/jm050358b
A Positron Emission Tomography Radioligand for the in Vivo Labeling of Metabotropic Glutamate 1 Receptor: (3-Ethyl-2-[11C]methyl-6-quinolinyl)(cis- 4-methoxycyclohexyl)methanone
Yiyun Huang, Raj Narendran, François Bischoff, Ningning Guo, Zhihong Zhu, Sung-A Bae, Anne S. Lesage, and Marc Laruelle
pp 5096–5099Publication Date (Web): July 12, 2005 (Letter)
DOI: 10.1021/jm050263+
Full Text HTMLDiscovery of Potent Poly(ADP-ribose) Polymerase-1 Inhibitors from the Modification of Indeno[1,2-c]isoquinolinone
Prakash G. Jagtap, Erkan Baloglu, Garry J. Southan, Jon G. Mabley, Hongshan Li, Jing Zhou, John van Duzer, Andrew L. Salzman, and Csaba Szabó
pp 5100–5103Publication Date (Web): July 16, 2005 (Letter)
DOI: 10.1021/jm0502891
Design and Synthesis of Tricyclic Imidazo[4,5-b]pyridin-2-ones as Corticotropin-Releasing Factor-1 Antagonists
Zhiqiang Guo, John E. Tellew, Raymond S. Gross, Brian Dyck, Jonathan Grey, Mustapha Haddach, Mehrak Kiankarimi, Marion Lanier, Bin-Feng Li, Zhiyong Luo, James R. McCarthy, Manisha Moorjani, John Saunders, Robert Sullivan, Xiaohu Zhang, Said Zamani-Kord, Dimitri E. Grigoriadis, Paul D. Crowe, Ta Kung Chen, and John P. Williams
pp 5104–5107Publication Date (Web): July 09, 2005 (Letter)
DOI: 10.1021/jm050384+
Discovery of Cell-Permeable Non-Peptide Inhibitors of β-Secretase by High-Throughput Docking and Continuum Electrostatics Calculations
Danzhi Huang, Urs Lüthi, Peter Kolb, Karin Edler, Marco Cecchini, Stephan Audetat, Alcide Barberis, and Amedeo Caflisch
pp 5108–5111Publication Date (Web): July 08, 2005 (Letter)
DOI: 10.1021/jm050499d
Articles
A Novel Immunostimulator, N2-[α-O-Benzyl-N-(acetylmuramyl)-l-alanyl-d- isoglutaminyl]-N6-trans-(m-nitrocinnamoyl)-l-lysine, and Its Adjuvancy on the Hepatitis B Surface Antigen
Hong-Zhen Yang, Song Xu, Xue-Yan Liao, Suo-De Zhang, Zheng-Lun Liang, Bai-He Liu, Jin-Ye Bai, Chao Jiang, Jian Ding, Gui-Fang Cheng, and Gang Liu
pp 5112–5122Publication Date (Web): July 14, 2005 (Article)
DOI: 10.1021/jm0493313
Ligand Selectivity for the Acetylcholine Binding Site of the Rat α4β2 and α3β4 Nicotinic Subtypes Investigated by Molecular Docking
William H. Bisson, Leonardo Scapozza, Gerrit Westera, Linjing Mu, and P. A. Schubiger
pp 5123–5130Publication Date (Web): July 14, 2005 (Article)
DOI: 10.1021/jm040881a
6-Aryl-8H-indeno[1,2-d]thiazol-2-ylamines: A1 Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency
Mahendra D. Chordia, Molly Zigler, Lauren J. Murphree, Heidi Figler, Timothy L. Macdonald, Ray A. Olsson, and Joel Linden
pp 5131–5139Publication Date (Web): July 09, 2005 (Article)
DOI: 10.1021/jm049132j
Antifungal Agents. 11. N-Substituted Derivatives of 1-[(Aryl)(4-aryl-1H-pyrrol-3-yl)methyl]-1H-imidazole: Synthesis, Anti-Candida Activity, and QSAR Studies
Roberto Di Santo, Andrea Tafi, Roberta Costi, Maurizo Botta, Marino Artico, Federico Corelli, Michela Forte, Fabiana Caporuscio, Letizia Angiolella, and Anna Teresa Palamara
pp 5140–5153Publication Date (Web): July 07, 2005 (Article)
DOI: 10.1021/jm048997u
A Rapid Computational Filter for Cytochrome P450 1A2 Inhibition Potential of Compound Libraries
Kamaldeep K. Chohan, Stuart W. Paine, Jaina Mistry, Patrick Barton, and Andrew M. Davis
pp 5154–5161Publication Date (Web): July 12, 2005 (Article)
DOI: 10.1021/jm048959a
Novel, Highly Potent Adenosine Deaminase Inhibitors Containing the Pyrazolo[3,4-d]pyrimidine Ring System. Synthesis, Structure−Activity Relationships, and Molecular Modeling Studies
Federico Da Settimo, Giampaolo Primofiore, Concettina La Motta, Sabrina Taliani, Francesca Simorini, Anna Maria Marini, Laura Mugnaini, Antonio Lavecchia, Ettore Novellino, Daniela Tuscano, and Claudia Martini
pp 5162–5174Publication Date (Web): July 09, 2005 (Article)
DOI: 10.1021/jm050136d
Structure-Based Design, Synthesis, and Memapsin 2 (BACE) Inhibitory Activity of Carbocyclic and Heterocyclic Peptidomimetics
Stephen Hanessian, Hongying Yun, Yihua Hou, Gaoqiang Yang, Malken Bayrakdarian, Eric Therrien, Nicolas Moitessier, Silvio Roggo, Siem Veenstra, Marina Tintelnot-Blomley, Jean-Michel Rondeau, Christian Ostermeier, André Strauss, Paul Ramage, Paolo Paganetti, Ulf Neumann, and Claudia Betschart
pp 5175–5190Publication Date (Web): July 15, 2005 (Article)
DOI: 10.1021/jm050142+
Application of Fluorescence Microscopy for Investigation of Cellular Distribution of Dinuclear Platinum Anticancer Drugs
Ganna V. Kalayda, Guofang Zhang, Tsion Abraham, Hans J. Tanke, and Jan Reedijk
pp 5191–5202Publication Date (Web): July 16, 2005 (Article)
DOI: 10.1021/jm050216h
Novel 17β-Substituted Conformationally Constrained Neurosteroids that Modulate GABAA Receptors
Charikleia Souli, Nicolaos Avlonitis, Theodora Calogeropoulou, Andrew Tsotinis, Gábor Maksay, Tímea Bíró, Aggeliki Politi, Thomas Mavromoustakos, Alexandros Makriyannis, Heribert Reis, and Manthos Papadopoulos
pp 5203–5214Publication Date (Web): July 20, 2005 (Article)
DOI: 10.1021/jm050271q
Discovery and Structure−Activity Relationship of 3-Aryl-5-aryl-1,2,4-oxadiazoles as a New Series of Apoptosis Inducers and Potential Anticancer Agents
Han-Zhong Zhang, Shailaja Kasibhatla, Jared Kuemmerle, William Kemnitzer, Kristin Ollis-Mason, Ling Qiu, Candace Crogan-Grundy, Ben Tseng, John Drewe, and Sui Xiong Cai
pp 5215–5223Publication Date (Web): July 13, 2005 (Article)
DOI: 10.1021/jm050292k
2-Acetylamino-3-[4-(2-acetylamino-2-carboxyethylsulfanylcarbonylamino)- phenylcarbamoylsulfanyl]propionic Acid and Its Derivatives as a Novel Class of Glutathione Reductase Inhibitors
Teresa Seefeldt, Chandradhar Dwivedi, Greg Peitz, Jocqueline Herman, Laura Carlson, Zhiling Zhang, and Xiangming Guan
pp 5224–5231Publication Date (Web): July 15, 2005 (Article)
DOI: 10.1021/jm050030i
A Chiral Benzoquinolizine-2-carboxylic Acid Arginine Salt Active against Vancomycin-Resistant Staphylococcus aureus
Noel J. de Souza, Shrikant V. Gupte, Prasad K. Deshpande, Vijaya N. Desai, Satish B. Bhawsar, Ravindra D. Yeole, Milind C. Shukla, Jacob Strahilevitz, David C. Hooper, Bülent Bozdogan, Peter C. Appelbaum, Michael R. Jacobs, Nitin Shetty, Mahesh V. Patel, Rasendrakumar Jha, and Habil F. Khorakiwala
pp 5232–5242Publication Date (Web): July 12, 2005 (Article)
DOI: 10.1021/jm050035f
A-Ring-Substituted Estrogen-3-O-sulfamates: Potent Multitargeted Anticancer Agents
Mathew P. Leese, Hatem A. M. Hejaz, Mary F. Mahon, Simon P. Newman, Atul Purohit, Michael J. Reed, and Barry V. L. Potter
pp 5243–5256Publication Date (Web): July 01, 2005 (Article)
DOI: 10.1021/jm050066a
Androsterone 3α-Ether-3β-Substituted and Androsterone 3β-Substituted Derivatives as Inhibitors of Type 3 17β-Hydroxysteroid Dehydrogenase: Chemical Synthesis and Structure−Activity Relationship
Béatrice Tchédam Ngatcha, Van Luu-The, Fernand Labrie, and Donald Poirier
pp 5257–5268Publication Date (Web): July 09, 2005 (Article)
DOI: 10.1021/jm058179h
Syntheses and Biological Activities of Disaccharide Daunorubicins
Guisheng Zhang, Lanyan Fang, Lizhi Zhu, Josephine E. Aimiuwu, Jie Shen, Hao Cheng, Mark T. Muller, Gun Eui Lee, Duxin Sun, and Peng George Wang
pp 5269–5278Publication Date (Web): July 12, 2005 (Article)
DOI: 10.1021/jm050144u
Development of Dual-Acting Benzofurans for Thromboxane A2 Receptor Antagonist and Prostacyclin Receptor Agonist: Synthesis, Structure−Activity Relationship, and Evaluation of Benzofuran Derivatives
Michihiro Ohno, Mitsuko Miyamoto, Kazuhiro Hoshi, Takahiro Takeda, Naohiro Yamada, and Atsushi Ohtake
pp 5279–5294Publication Date (Web): July 15, 2005 (Article)
DOI: 10.1021/jm050194z
Antidiabetic Activity of Passive Nonsteroidal Glucocorticoid Receptor Modulators
J. T. Link, Bryan Sorensen, Jyoti Patel, Marlena Grynfarb, Annika Goos-Nilsson, Jiahong Wang, Steven Fung, Denise Wilcox, Brad Zinker, Phong Nguyen, Bach Hickman, James M. Schmidt, Sue Swanson, Zhenping Tian, Thomas J. Reisch, Gary Rotert, Jia Du, Benjamin Lane, Thomas W. von Geldern, and Peer B. Jacobson
pp 5295–5304Publication Date (Web): July 13, 2005 (Article)
DOI: 10.1021/jm050205o
Dipeptides as Effective Prodrugs of the Unnatural Amino Acid (+)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic Acid (LY354740), a Selective Group II Metabotropic Glutamate Receptor Agonist
Ana Belén Bueno, Iván Collado, Alfonso de Dios, Carmen Domínguez, José Alfredo Martín, Luisa M. Martín, María Angeles Martínez-Grau, Carlos Montero, Concepción Pedregal, John Catlow, D. Scott Coffey, Michael P. Clay, Anne H. Dantzig, Terry Lindstrom, James A. Monn, Haiyan Jiang, Darryle D. Schoepp, Robert E. Stratford, Linda B. Tabas, Joseph P. Tizzano, Rebecca A. Wright, and Marc F. Herin
pp 5305–5320Publication Date (Web): July 15, 2005 (Article)
DOI: 10.1021/jm050235r
Novel Fluorinated Prodrugs for Activation by Carboxypeptidase G2 Showing Good in Vivo Antitumor Activity in Gene-Directed Enzyme Prodrug Therapy
Lawrence C. Davies, Frank Friedlos, Douglas Hedley, Jan Martin, Lesley M. Ogilvie, Ian J. Scanlon, and Caroline J. Springer
pp 5321–5328Publication Date (Web): July 12, 2005 (Article)
DOI: 10.1021/jm0502182
Synthesis of Classical, Four-Carbon Bridged 5-Substituted Furo[2,3-d]pyrimidine and 6-Substituted Pyrrolo[2,3-d]pyrimidine Analogues as Antifolates1
Aleem Gangjee, Yibin Zeng, John J. McGuire, and Roy L. Kisliuk
pp 5329–5336Publication Date (Web): July 09, 2005 (Article)
DOI: 10.1021/jm058213s
High-Affinity Epidermal Growth Factor Receptor (EGFR) Irreversible Inhibitors with Diminished Chemical Reactivities as Positron Emission Tomography (PET)-Imaging Agent Candidates of EGFR Overexpressing Tumors
Eyal Mishani, Galith Abourbeh, Orit Jacobson, Samar Dissoki, Revital Ben Daniel, Yulia Rozen, Mazal Shaul, and Alexander Levitzki
pp 5337–5348Publication Date (Web): July 12, 2005 (Article)
DOI: 10.1021/jm0580196
Designer Antibacterial Peptides Kill Fluoroquinolone-Resistant Clinical Isolates
Laszlo Otvos, Jr., John D. Wade, Feng Lin, Barry A. Condie, Joerg Hanrieder, and Ralf Hoffmann
pp 5349–5359Publication Date (Web): July 16, 2005 (Article)
DOI: 10.1021/jm050347i
Mechanism of Poly(acrylic acid) Acceleration of Antithrombin Inhibition of Thrombin: Implications for the Design of Novel Heparin Mimics
Bernhard H. Monien, Kai I. Cheang, and Umesh R. Desai
pp 5360–5368Publication Date (Web): July 13, 2005 (Article)
DOI: 10.1021/jm0503648
Brief Articles
Design and Synthesis of 4-(α-Hydroxymalonyl)phenylalanine as a New Phosphotyrosyl Mimetic and Its Use in Growth Factor Receptor Bound 2 Src-Homology 2 (Grb2 SH2) Domain-Binding Peptides
Sang-Uk Kang, Karen M. Worthy, Lakshman K. Bindu, Manchao Zhang, Dajun Yang, Robert J. Fisher, and Terrence R. Burke, Jr.
pp 5369–5372Publication Date (Web): July 12, 2005 (Brief Article)
DOI: 10.1021/jm050154v
Novel Immunomodulator FTY720 Is Phosphorylated in Rats and Humans To Form a Single Stereoisomer. Identification, Chemical Proof, and Biological Characterization of the Biologically Active Species and Its Enantiomer
Rainer Albert, Klaus Hinterding, Volker Brinkmann, Danilo Guerini, Constanze Müller-Hartwieg, Helmut Knecht, Corinne Simeon, Markus Streiff, Trixie Wagner, Karl Welzenbach, Frédéric Zécri, Markus Zollinger, Nigel Cooke, and Eric Francotte
pp 5373–5377Publication Date (Web): July 09, 2005 (Brief Article)
DOI: 10.1021/jm050242f
Efficient Transfection of DNA by Liposomes Formulated with Cationic Gemini Amphiphiles
Cecilia Bombelli, Francesca Faggioli, Paola Luciani, Giovanna Mancini, and Maria Grazia Sacco
pp 5378–5382Publication Date (Web): July 06, 2005 (Brief Article)
DOI: 10.1021/jm050477r