Table of Contents
March 25, 2004
Volume 47, Issue 7
Pages 1595-1868
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).
Letters
Pyrazolo[3,4-d]pyrimidines Endowed with Antiproliferative Activity on Ductal Infiltrating Carcinoma Cells
Fabio Carraro, Annalisa Pucci, Antonella Naldini, Silvia Schenone, Olga Bruno, Angelo Ranise, Francesco Bondavalli, Chiara Brullo, Paola Fossa, Giulia Menozzi, Luisa Mosti, Fabrizio Manetti, and Maurizio Botta
pp 1595–1598Publication Date (Web): February 21, 2004 (Letter)
DOI: 10.1021/jm034257u
Hi-Res PDF7-Alkoxy-4-phenylamino-3-quinolinecar-bonitriles as Dual Inhibitors of Src and Abl Kinases
Diane H. Boschelli, Yanong D. Wang, Steve Johnson, Biqi Wu, Fei Ye, Ana Carolina Barrios Sosa, Jennifer M. Golas, and Frank Boschelli
pp 1599–1601Publication Date (Web): February 27, 2004 (Letter)
DOI: 10.1021/jm0499458
Identification of 2-{2-[2-(5-Bromo-2- methoxyphenyl)-ethyl]-3-fluorophenyl}-4,5-dihydro-1H-imidazole (ML00253764), a Small Molecule Melanocortin 4 Receptor Antagonist That Effectively Reduces Tumor-Induced Weight Loss in a Mouse Model
Tricia J. Vos, Andrei Caracoti, Jennifer L. Che, Mingshi Dai, Cheryl A. Farrer, Nancy E. Forsyth, Stacey V. Drabic, Robert A. Horlick, Diana Lamppu, David L. Yowe, Suresh Balani, Ping Li, Hang Zeng, Ingrid B. J. K. Joseph, Luis E. Rodriguez, Martin P. Maguire, Michael A. Patane, and Christopher F. Claiborne
pp 1602–1604Publication Date (Web): February 28, 2004 (Letter)
DOI: 10.1021/jm034244g
Structure−Activity Study on a Novel Series of Macrocyclic Inhibitors of the Hepatitis C Virus NS3 Protease Leading to the Discovery of BILN 2061
Montse Llinàs-Brunet, Murray D. Bailey, Gordon Bolger, Christian Brochu, Anne-Marie Faucher, Jean Marie Ferland, Michel Garneau, Elise Ghiro, Vida Gorys, Chantal Grand-Maître, Ted Halmos, Nicole Lapeyre-Paquette, Francine Liard, Martin Poirier, Manon Rhéaume, Youla S. Tsantrizos, and Daniel Lamarre
pp 1605–1608Publication Date (Web): March 02, 2004 (Letter)
DOI: 10.1021/jm0342414
Design and Synthesis of a Fluoroindolocarbazole Series as Selective Topoisomerase I Active Agents. Discovery of Water-Soluble 3,9-Difluoro-12,13-dihydro-13-[6-amino-β- d-glucopyranosyl]-5H,13H-benzo[b]- thienyl[2,3-a]pyrrolo[3,4-c]carbazole- 5,7(6H)-dione (BMS-251873) with Curative Antitumor Activity against Prostate Carcinoma Xenograft Tumor Model
Balu N. Balasubramanian, Denis R. St. Laurent, Mark G. Saulnier, Byron H. Long, Carol Bachand, Francis Beaulieu, Wendy Clarke, Milind Deshpande, Jeffrey Eummer, Craig R. Fairchild, David B. Frennesson, Robert Kramer, Frank Y. Lee, Mikael Mahler, Alain Martel, B. Narasimhulu Naidu, William C. Rose, John Russell, Edward Ruediger, Carola Solomon, Karen M. Stoffan, Henry Wong, Kurt Zimmermann, and Dolatrai M. Vyas
pp 1609–1612Publication Date (Web): February 20, 2004 (Letter)
DOI: 10.1021/jm034197s
Predicting the Cell Differentiation Activity of 1α,25-Dihydroxyvitamin D3 Side Chain Analogues from Docking Simulations
Fredy Sussman, Antonio Rumbo, M. Carmen Villaverde, and Antonio Mouriño
pp 1613–1616Publication Date (Web): March 02, 2004 (Letter)
DOI: 10.1021/jm034157o
Articles
A New Series of Highly Potent Non-Peptide Bradykinin B2 Receptor Antagonists Incorporating the 4-Heteroarylquinoline Framework. Improvement of Aqueous Solubility and New Insights into Species Difference
Yuki Sawada, Hiroshi Kayakiri, Yoshito Abe, Keisuke Imai, Tsuyoshi Mizutani, Noriaki Inamura, Masayuki Asano, Ichiro Aramori, Chie Hatori, Akira Katayama, Teruo Oku, and Hirokazu Tanaka
pp 1617–1630Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm030159x
Synthesis, Structure−Activity Relationships, and Mechanism of Drug Resistance of d- and l-β-3‘-Fluoro-2‘,3‘-unsaturated-4‘-thionucleosides as Anti-HIV Agents
Wei Zhu, Youhoon Chong, Hyunah Choo, Judy Mathews, Raymond F. Schinazi, and Chung K. Chu
pp 1631–1640Publication Date (Web): February 19, 2004 (Article)
DOI: 10.1021/jm0303148
Countering Cooperative Effects in Protease Inhibitors Using Constrained β-Strand-Mimicking Templates in Focused Combinatorial Libraries
Robert C. Reid, Leonard K. Pattenden, Joel D. A. Tyndall, Jennifer L. Martin, Terry Walsh, and David P. Fairlie
pp 1641–1651Publication Date (Web): February 19, 2004 (Article)
DOI: 10.1021/jm030337m
Unraveling the Active Conformation of Urotensin II
Alfonso Carotenuto, Paolo Grieco, Pietro Campiglia, Ettore Novellino, and Paolo Rovero
pp 1652–1661Publication Date (Web): February 19, 2004 (Article)
DOI: 10.1021/jm0309912
2-Anilino-4-(thiazol-5-yl)pyrimidine CDK Inhibitors: Synthesis, SAR Analysis, X-ray Crystallography, and Biological Activity
Shudong Wang, Christopher Meades, Gavin Wood, Andrew Osnowski, Sian Anderson, Rhoda Yuill, Mark Thomas, Mokdad Mezna, Wayne Jackson, Carol Midgley, Gary Griffiths, Ian Fleming, Simon Green, Iain McNae, Su-Ying Wu, Campbell McInnes, Daniella Zheleva, Malcolm D. Walkinshaw, and Peter M. Fischer
pp 1662–1675Publication Date (Web): February 07, 2004 (Article)
DOI: 10.1021/jm0309957
Synthesis and Monoamine Transporter Binding of 2-(Diarylmethoxymethyl)-3β-aryltropane Derivatives
Lifen Xu, Santosh S. Kulkarni, Sari Izenwasser, Jonathan L. Katz, Theresa Kopajtic, Stacey A. Lomenzo, Amy Hauck Newman, and Mark L. Trudell
pp 1676–1682Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm030430a
Validation of Molecular Docking Calculations Involving FGF-1 and FGF-2
Ian Bytheway and Siska Cochran
pp 1683–1693Publication Date (Web): February 18, 2004 (Article)
DOI: 10.1021/jm030447t
Enzymatic Release of Antitumor Ether Lipids by Specific Phospholipase A2 Activation of Liposome-Forming Prodrugs
Thomas L. Andresen, Jesper Davidsen, Mikael Begtrup, Ole G. Mouritsen, and Kent Jørgensen
pp 1694–1703Publication Date (Web): February 24, 2004 (Article)
DOI: 10.1021/jm031029r
Discovery of a Potent and Novel Motilin Agonist
James J. Li, Hann-Guang Chao, Haixia Wang, Joseph A. Tino, R. Michael Lawrence, William R. Ewing, Zhengping Ma, Mujing Yan, Dorothy Slusarchyk, Ramakrishna Seethala, Huabin Sun, Danshi Li, Neil T. Burford, Robert H. Stoffel, Mary Ellen Salyan, Cindy Y. Li, Michael Witkus, Ning Zhao, Adam Rich, and David A. Gordon
pp 1704–1708Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm0304865
Discovery of Potent Inhibitors of Dihydroneopterin Aldolase Using CrystaLEAD High-Throughput X-ray Crystallographic Screening and Structure-Directed Lead Optimization
William J. Sanders, Vicki L. Nienaber, Claude G. Lerner, J. Owen McCall, Sean M. Merrick, Susan J. Swanson, John E. Harlan, Vincent S. Stoll, Geoffrey F. Stamper, Stephen F. Betz, Kevin R. Condroski, Robert P. Meadows, Jean M. Severin, Karl A. Walter, Peter Magdalinos, Clarissa G. Jakob, Rolf Wagner, and Bruce A. Beutel
pp 1709–1718Publication Date (Web): February 18, 2004 (Article)
DOI: 10.1021/jm030497y
N-(Cycloalkylamino)acyl-2-aminothiazole Inhibitors of Cyclin-Dependent Kinase 2. N-[5-[[[5-(1,1-Dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4- piperidinecarboxamide (BMS-387032), a Highly Efficacious and Selective Antitumor Agent
Raj N. Misra, Hai-yun Xiao, Kyoung S. Kim, Songfeng Lu, Wen-Ching Han, Stephanie A. Barbosa, John T. Hunt, David B. Rawlins, Weifang Shan, Syed Z. Ahmed, Ligang Qian, Bang-Chi Chen, Rulin Zhao, Mark S. Bednarz, Kristen A. Kellar, Janet G. Mulheron, Roberta Batorsky, Urvashi Roongta, Amrita Kamath, Punit Marathe, Sunanda A. Ranadive, John S. Sack, John S. Tokarski, Nikola P. Pavletich, Francis Y. F. Lee, Kevin R. Webster, and S. David Kimball
pp 1719–1728Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm0305568
Synthesis of Urea-Based Inhibitors as Active Site Probes of Glutamate Carboxypeptidase II: Efficacy as Analgesic Agents
Alan P. Kozikowski, Jiazhong Zhang, Fajun Nan, Pavel A. Petukhov, Ewa Grajkowska, Jarda T. Wroblewski, Tatsuo Yamamoto, Tomasz Bzdega, Barbara Wroblewska, and Joseph H. Neale
pp 1729–1738Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm0306226
Glide: A New Approach for Rapid, Accurate Docking and Scoring. 1. Method and Assessment of Docking Accuracy
Richard A. Friesner, Jay L. Banks, Robert B. Murphy, Thomas A. Halgren, Jasna J. Klicic, Daniel T. Mainz, Matthew P. Repasky, Eric H. Knoll, Mee Shelley, Jason K. Perry, David E. Shaw, Perry Francis, and Peter S. Shenkin
pp 1739–1749Publication Date (Web): February 27, 2004 (Article)
DOI: 10.1021/jm0306430
Glide: A New Approach for Rapid, Accurate Docking and Scoring. 2. Enrichment Factors in Database Screening
Thomas A. Halgren, Robert B. Murphy, Richard A. Friesner, Hege S. Beard, Leah L. Frye, W. Thomas Pollard, and Jay L. Banks
pp 1750–1759Publication Date (Web): February 27, 2004 (Article)
DOI: 10.1021/jm030644s
Inactivation of Purified Human Recombinant Monoamine Oxidases A and B by Rasagiline and Its Analogues
Frantisek Hubálek, Claudia Binda, Min Li, Yaacov Herzig, Jeffrey Sterling, Moussa B. H. Youdim, Andrea Mattevi, and Dale E. Edmondson
pp 1760–1766Publication Date (Web): February 27, 2004 (Article)
DOI: 10.1021/jm0310885
Crystal Structures of Monoamine Oxidase B in Complex with Four Inhibitors of the N-Propargylaminoindan Class
Claudia Binda, Frantisek Hubálek, Min Li, Yaacov Herzig, Jeffrey Sterling, Dale E. Edmondson, and Andrea Mattevi
pp 1767–1774Publication Date (Web): February 27, 2004 (Article)
DOI: 10.1021/jm031087c
Antineoplastic Agents. 499. Synthesis of Hystatin 2 and Related 1H-Benzo[de][1,6]-naphthyridinium Salts from Aaptamine1
George R. Pettit, Holger Hoffmann, Delbert L. Herald, Peter M. Blumberg, Ernest Hamel, Jean M. Schmidt, Yung Chang, Robin K. Pettit, Nancy E. Lewin, and Larry V. Pearce
pp 1775–1782Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm030070r
Surface Activity Profiling of Drugs Applied to the Prediction of Blood−Brain Barrier Permeability
Pekka Suomalainen, Christoffer Johans, Tim Söderlund, and Paavo K. J. Kinnunen
pp 1783–1788Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm0309001
Synthesis and Biological Evaluation in Human Monocyte-Derived Macrophages of N-(N-Acetyl-l-cysteinyl)-S-acetylcysteamine Analogues with Potent Antioxidant and Anti-HIV Activities
Joël Oiry, Patricia Mialocq, Jean-Yves Puy, Philippe Fretier, Nathalie Dereuddre-Bosquet, Dominique Dormont, Jean-Louis Imbach, and Pascal Clayette
pp 1789–1795Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm030374d
Fluorinated Phenylcyclopropylamines. 1. Synthesis and Effect of Fluorine Substitution at the Cyclopropane Ring on Inhibition of Microbial Tyramine Oxidase
Shinichi Yoshida, Oliver G. J. Meyer, Thomas C. Rosen, Günter Haufe, Song Ye, Milton J. Sloan, and Kenneth L. Kirk
pp 1796–1806Publication Date (Web): February 27, 2004 (Article)
DOI: 10.1021/jm030398k
3-Phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-a]phthalazines and Analogues: High-Affinity γ-Aminobutyric Acid-A Benzodiazepine Receptor Ligands with α2, α3, and α5-Subtype Binding Selectivity over α1
Robert W. Carling, Kevin W. Moore, Leslie J. Street, Deborah Wild, Catherine Isted, Paul D. Leeson, Steven Thomas, Desmond O'Connor, Ruth M. McKernan, Katherine Quirk, Susan M. Cook, John R. Atack, Keith A. Wafford, Sally A. Thompson, Gerard R. Dawson, Pushpinder Ferris, and José L. Castro
pp 1807–1822Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm031020p
Synthesis and Antitubulin Activity of N1- and N4-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania
Gautam Bhattacharya, Johnathan Herman, Dawn Delfín, Manar M. Salem, Todd Barszcz, Mike Mollet, Guy Riccio, Reto Brun, and Karl A. Werbovetz
pp 1823–1832Publication Date (Web): February 14, 2004 (Article)
DOI: 10.1021/jm0304461
Novel Endoperoxide Antimalarials: Synthesis, Heme Binding, and Antimalarial Activity
Dennis K. Taylor, Thomas D. Avery, Ben W. Greatrex, Edward R. T. Tiekink, Ian G. Macreadie, Peter I. Macreadie, Adam D. Humphries, Martha Kalkanidis, Emma N. Fox, Nectarios Klonis, and Leann Tilley
pp 1833–1839Publication Date (Web): February 27, 2004 (Article)
DOI: 10.1021/jm0305319
Design and Synthesis of 3‘- and 5‘-O-(3-Benzenesulfonylfuroxan-4-yl)-2‘-deoxyuridines: Biological Evaluation as Hybrid Nitric Oxide Donor−Nucleoside Anticancer Agents
Sameh Moharram, Aihua Zhou, Leonard I. Wiebe, and Edward E. Knaus
pp 1840–1846Publication Date (Web): February 24, 2004 (Article)
DOI: 10.1021/jm030544m
Brief Articles
Discovery of a New Family of Inhibitors of Human Cytomegalovirus (HCMV) Based upon Lipophilic Alkyl Furano Pyrimidine Dideoxy Nucleosides: Action via a Novel Non-Nucleosidic Mechanism
Christopher McGuigan, Ranjith N. Pathirana, Robert Snoeck, Graciela Andrei, Erik De Clercq, and Jan Balzarini
pp 1847–1851Publication Date (Web): March 02, 2004 (Article)
DOI: 10.1021/jm030857h
N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides. A New Class of Potent and Selective Ligands at the Peripheral Benzodiazepine Receptor
Giampaolo Primofiore, Federico Da Settimo, Sabrina Taliani, Francesca Simorini, Maria Paola Patrizi, Ettore Novellino, Giovanni Greco, Enrico Abignente, Barbara Costa, Beatrice Chelli, and Claudia Martini
pp 1852–1855Publication Date (Web): February 24, 2004 (Brief Article)
DOI: 10.1021/jm030973k
Synthesis and Biological Evaluation of Novel Chloroethylaminoanthraquinones with Potent Cytotoxic Activity against Cisplatin-Resistant Tumor Cells
Klaus Pors, Zennia Paniwnyk, Ketan C. Ruparelia, Paul H. Teesdale-Spittle, John A. Hartley, Lloyd R. Kelland, and Laurence H. Patterson
pp 1856–1859Publication Date (Web): February 27, 2004 (Brief Article)
DOI: 10.1021/jm031070u
QSAR Study of Anticonvulsant Negative Allosteric Modulators of the AMPA Receptor
Antonio Macchiarulo, Laura De Luca, Gabriele Costantino, Maria Letizia Barreca, Rosaria Gitto, Roberto Pellicciari, and Alba Chimirri
pp 1860–1863Publication Date (Web): March 02, 2004 (Brief Article)
DOI: 10.1021/jm0310838
Structure−Activity Study of the ORL1 Antagonist Ac-Arg-d-Cha-Qaa-d-Arg-d-p-ClPhe-NH2
Sylvia Van Cauwenberghe, Frédéric Simonin, Jérôme Cluzeau, Jérôme A. J. Becker, William. D. Lubell, and Dirk Tourwé
pp 1864–1867Publication Date (Web): March 03, 2004 (Brief Article)
DOI: 10.1021/jm031034v
Book Reviews
Drug Bioavailability: Estimation of Solubility, Permeability, Absorption and Bioavailability Edited by H. van de Waterbeemd, H. Lennemas, and P. Artursson. Wiley-VCH, Weinheim, Germany. 2003. xvii + 579 pp. 18 × 24.5 cm. ISBN 3-527-30438-X. $195.00.
Gordon L. Amidon
p 1868Publication Date (Web): February 27, 2004 (Book Review)
DOI: 10.1021/jm040011t
Absorption and Drug Development By Alex Avdeef. Wiley/Interscience, Hoboken, NJ. 2003. xxiv + 287 pp. 16 × 24 cm. ISBN 0471423653. $89.95.
Samuel H. Yalkowsky
p 1868Publication Date (Web): February 24, 2004 (Book Review)
DOI: 10.1021/jm040012l