Table of Contents
April 21, 2005
Volume 48, Issue 8
Pages 2725-3094
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).
Perspective
Cytochrome P450 in Silico: An Integrative Modeling Approach
Chris de Graaf, Nico P. E. Vermeulen, and K. Anton Feenstra
pp 2725–2755Publication Date (Web): April 14, 2005 (Perspective)
DOI: 10.1021/jm040180d
Hi-Res PDF Letters
Discovery of S-Phase Arresting Agents Derived from Noscapine
James T. Anderson, Anthony E. Ting, Sherry Boozer, Kurt R. Brunden, Joel Danzig, Tom Dent, John J. Harrington, Steven M. Murphy, Rob Perry, Amy Raber, Stephen E. Rundlett, Jianmin Wang, Nancy Wang, and Youssef L. Bennani
pp 2756–2758Publication Date (Web): March 30, 2005 (Letter)
DOI: 10.1021/jm0494220
Novel and Potent 17β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors
Harshani R. Lawrence, Nigel Vicker, Gillian M. Allan, Andrew Smith, Mary F. Mahon, Helena J. Tutill, Atul Purohit, Michael J. Reed, and Barry V. L. Potter
pp 2759–2762Publication Date (Web): March 25, 2005 (Letter)
DOI: 10.1021/jm049045r
Effects of 5‘-Phosphate Derivatives of 2-Hexynyl Adenosine and 2-Phenylethynyl Adenosine on Responses of Human Platelets Mediated by P2Y Receptors
Gloria Cristalli, Gian Marco Podda, Stefano Costanzi, Catia Lambertucci, Anna Lecchi, Sauro Vittori, Rosaria Volpini, Maddalena L. Zighetti, and Marco Cattaneo
pp 2763–2766Publication Date (Web): March 16, 2005 (Letter)
DOI: 10.1021/jm0493562
Articles
Synthesis and Monoamine Transporter Binding Properties of 3β-(3‘,4‘-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl Esters
F. Ivy Carroll, Bruce E. Blough, Zhe Nie, Michael J. Kuhar, Leonard L. Howell, and Hernan A. Navarro
pp 2767–2771Publication Date (Web): March 18, 2005 (Article)
DOI: 10.1021/jm040185a
Synthesis and Biological Evaluation of 11-Substituted 6-Aminobenzo[c]phenanthridine Derivatives, a New Class of Antitumor Agents
Ilka Kock, Dieter Heber, Matthias Weide, Ulrich Wolschendorf, and Bernd Clement
pp 2772–2777Publication Date (Web): March 05, 2005 (Article)
DOI: 10.1021/jm0490888
N-Terminal Sugar Conjugation and C-Terminal Thr-for-Thr(ol) Exchange in Radioiodinated Tyr3-octreotide: Effect on Cellular Ligand Trafficking in Vitro and Tumor Accumulation in Vivo
Margret Schottelius, Jean Claude Reubi, Veronique Eltschinger, Markus Schwaiger, and Hans-Jürgen Wester
pp 2778–2789Publication Date (Web): March 01, 2005 (Article)
DOI: 10.1021/jm040794i
Effects of Flavonoids on Cell Proliferation and Caspase Activation in a Human Colonic Cell Line HT29: An SAR Study
Jean-Baptiste Daskiewicz, Flore Depeint, Lionel Viornery, Christine Bayet, Geraldine Comte-Sarrazin, Gilles Comte, Jennifer M. Gee, Ian T. Johnson, Karine Ndjoko, Kurt Hostettmann, and Denis Barron
pp 2790–2804Publication Date (Web): March 30, 2005 (Article)
DOI: 10.1021/jm040770b
In Vitro Metabolism of Phenoxypropoxybiguanide Analogues in Human Liver Microsomes to Potent Antimalarial Dihydrotriazines
Todd. W. Shearer, Michael. P. Kozar, Michael T. O'Neil, Philip L. Smith, Guy A. Schiehser, David. P. Jacobus, Damaris S. Diaz, Young-Sun Yang, Wilbur. K. Milhous, and Donald. R. Skillman
pp 2805–2813Publication Date (Web): March 18, 2005 (Article)
DOI: 10.1021/jm049683+
Full Text HTMLSelective Estrogen Receptor Modulators in the Ruthenocene Series. Synthesis and Biological Behavior
Pascal Pigeon, Siden Top, Anne Vessières, Michel Huché, Elizabeth A. Hillard, Emmanuel Salomon, and Gérard Jaouen
pp 2814–2821Publication Date (Web): March 12, 2005 (Article)
DOI: 10.1021/jm049268h
Synthesis and Activity of Substituted Anthraquinones against a Human Filarial Parasite, Brugia malayi
Mugunthu R. Dhananjeyan, Youli P. Milev, Michael A. Kron, and Muraleedharan G. Nair
pp 2822–2830Publication Date (Web): March 05, 2005 (Article)
DOI: 10.1021/jm0492655
Redox-Active Antineoplastic Ruthenium Complexes with Indazole: Correlation of in Vitro Potency and Reduction Potential
Michael A. Jakupec, Erwin Reisner, Anna Eichinger, Martina Pongratz, Vladimir B. Arion, Markus Galanski, Christian G. Hartinger, and Bernhard K. Keppler
pp 2831–2837Publication Date (Web): March 12, 2005 (Article)
DOI: 10.1021/jm0490742
Thrombospondin-1 Mimetic Peptide Inhibitors of Angiogenesis and Tumor Growth: Design, Synthesis, and Optimization of Pharmacokinetics and Biological Activities
Fortuna Haviv, Michael F. Bradley, Douglas M. Kalvin, Andrew J. Schneider, Donald J. Davidson, Sandra M. Majest, Laura M. McKay, Catherine J. Haskell, Randy L. Bell, Bach Nguyen, Kennan C. Marsh, Bruce W. Surber, John T. Uchic, James Ferrero, Yi-Chun Wang, Juan Leal, Rae D. Record, Jason Hodde, Stephen F. Badylak, Richard R. Lesniewski, and Jack Henkin
pp 2838–2846Publication Date (Web): March 22, 2005 (Article)
DOI: 10.1021/jm0401560
Studies on the Mechanism of Inactivation of the HIV-1 Nucleocapsid Protein NCp7 with 2-Mercaptobenzamide Thioesters
Lisa M. Miller Jenkins, J. Calvin Byrd, Toshiaki Hara, Pratibha Srivastava, Sharlyn J. Mazur, Stephen J. Stahl, John K. Inman, Ettore Appella, James G. Omichinski, and Pascale Legault
pp 2847–2858Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jm0492195
1-Methyl-3H-pyrazolo[1,2-a]benzo[1,2,3,4]tetrazin-3-ones. Design, Synthesis, and Biological Activity of New Antitumor Agents
Anna Maria Almerico, Francesco Mingoia, Patrizia Diana, Paola Barraja, Antonino Lauria, Alessandra Montalbano, Girolamo Cirrincione, and Gaetano Dattolo
pp 2859–2866Publication Date (Web): March 15, 2005 (Article)
DOI: 10.1021/jm049075u
Design, Synthesis, and Antiviral Activity of Adenosine 5‘-Phosphonate Analogues as Chain Terminators against Hepatitis C Virus
Yung-hyo Koh, Jae Hoon Shim, Jim Zhen Wu, Weidong Zhong, Zhi Hong, and Jean-Luc Girardet
pp 2867–2875Publication Date (Web): March 15, 2005 (Article)
DOI: 10.1021/jm049029u
Synthesis and Pharmacology of Ethylphenidate Enantiomers: The Human Transesterification Metabolite of Methylphenidate and Ethanol
Kennerly S. Patrick, Robin L. Williard, Adam L. VanWert, Justin J. Dowd, John E. Oatis, Jr., and Lawrence D. Middaugh
pp 2876–2881Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jm0490989
(5-Arylfuran-2-ylcarbonyl)guanidines as Cardioprotectives through the Inhibition of Na+/H+ Exchanger Isoform-1
Sunkyung Lee, Kyu Yang Yi, Sun Kyung Hwang, Byung Ho Lee, Sung-eun Yoo, and Kyunghee Lee
pp 2882–2891Publication Date (Web): March 30, 2005 (Article)
DOI: 10.1021/jm0492305
Evaluation of 8-Arylsulfanyl, 8-Arylsulfoxyl, and 8-Arylsulfonyl Adenine Derivatives as Inhibitors of the Heat Shock Protein 90
Laura Llauger, Huazhong He, Joungnam Kim, Julia Aguirre, Neal Rosen, Ulf Peters, Peter Davies, and Gabriela Chiosis
pp 2892–2905Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jm049012b
Identification and Characterization of Novel Benzil (Diphenylethane-1,2-dione) Analogues as Inhibitors of Mammalian Carboxylesterases
Randy M. Wadkins, Janice L. Hyatt, Xin Wei, Kyoung Jin P. Yoon, Monika Wierdl, Carol C. Edwards, Christopher L. Morton, John C. Obenauer, Komath Damodaran, Paul Beroza, Mary K. Danks, and Philip M. Potter
pp 2906–2915Publication Date (Web): March 29, 2005 (Article)
DOI: 10.1021/jm049011j
Structure−Activity Relationship Studies Optimizing the Antiproliferative Activity of Novel Cyclic Somatostatin Analogues Containing a Restrained Cyclic β-Amino Acid
Martin Sukopp, Richard Schwab, Luciana Marinelli, Eric Biron, Markus Heller, Edit Várkondi, Ákos Pap, Ettore Novellino, György Kéri, and Horst Kessler
pp 2916–2926Publication Date (Web): March 19, 2005 (Article)
DOI: 10.1021/jm049500j
A Pharmacophore Hypothesis for P-Glycoprotein Substrate Recognition Using GRIND-Based 3D-QSAR
Giovanni Cianchetta, Robert W. Singleton, Meng Zhang, Marianne Wildgoose, Dennis Giesing, Arnaldo Fravolini, Gabriele Cruciani, and Roy J. Vaz
pp 2927–2935Publication Date (Web): March 16, 2005 (Article)
DOI: 10.1021/jm0491851
High Affinity Central Benzodiazepine Receptor Ligands: Synthesis and Biological Evaluation of a Series of Phenyltriazolobenzotriazindione Derivatives
Giampaolo Primofiore, Federico Da Settimo, Sabrina Taliani, Silvia Salerno, Ettore Novellino, Giovanni Greco, Barbara Cosimelli, François Besnard, Barbara Costa, Marina Montali, and Claudia Martini
pp 2936–2943Publication Date (Web): March 11, 2005 (Article)
DOI: 10.1021/jm0408722
3-Aminopyrazole Inhibitors of CDK2/Cyclin A as Antitumor Agents. 2. Lead Optimization
Paolo Pevarello, Maria Gabriella Brasca, Paolo Orsini, Gabriella Traquandi, Antonio Longo, Marcella Nesi, Fabrizio Orzi, Claudia Piutti, Pietro Sansonna, Mario Varasi, Alexander Cameron, Anna Vulpetti, Fulvia Roletto, Rachele Alzani, Marina Ciomei, Clara Albanese, Wilma Pastori, Aurelio Marsiglio, Enrico Pesenti, Francesco Fiorentini, Jim R. Bischoff, and Ciro Mercurio
pp 2944–2956Publication Date (Web): March 29, 2005 (Article)
DOI: 10.1021/jm0408870
Pyridinium-1-yl Bisphosphonates Are Potent Inhibitors of Farnesyl Diphosphate Synthase and Bone Resorption
John M. Sanders, Yongcheng Song, Julian M. W. Chan, Yonghui Zhang, Samuel Jennings, Thomas Kosztowski, Sarah Odeh, Ryan Flessner, Christine Schwerdtfeger, Evangelia Kotsikorou, Gary A. Meints, Aurora Ortiz Gómez, Dolores González-Pacanowska, Amy M. Raker, Hong Wang, Ermond R. van Beek, Socrates E. Papapoulos, Craig T. Morita, and Eric Oldfield
pp 2957–2963Publication Date (Web): March 08, 2005 (Article)
DOI: 10.1021/jm040209d
Dimeric Zanamivir Conjugates with Various Linking Groups Are Potent, Long-Lasting Inhibitors of Influenza Neuraminidase Including H5N1 Avian Influenza
Simon J. F. Macdonald, Rachel Cameron, Derek A. Demaine, Rob J. Fenton, Graham Foster, David Gower, J. Nicole Hamblin, Stephanie Hamilton, Graham J. Hart, Alan P. Hill, Graham G. A. Inglis, Betty Jin, Haydn T. Jones, Darryl B. McConnell, Jennifer McKimm-Breschkin, Gail Mills, Van Nguyen, Ian J. Owens, Nigel Parry, Stephen E. Shanahan, Donna Smith, Keith G. Watson, Wen-Yang Wu, and Simon P. Tucker
pp 2964–2971Publication Date (Web): March 16, 2005 (Article)
DOI: 10.1021/jm040891b
Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens: Synthesis, in Vitro Biological Activity, Pharmacokinetics, and Antitumor Activity in the LAPC4 Human Prostate Cancer Xenograft Model
Venkatesh D. Handratta, Tadas S. Vasaitis, Vincent C. O. Njar, Lalji K. Gediya, Ritesh Kataria, Pankaj Chopra, Donnell Newman, Jr., Rena Farquhar, Zhiyong Guo, Yun Qiu, and Angela M. H. Brodie
pp 2972–2984Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jm040202w
Imaging of Melanoma Using 64Cu− and 86Y−DOTA−ReCCMSH(Arg11), a Cyclized Peptide Analogue of α-MSH
Paul McQuade, Yubin Miao, Jeongsoo Yoo, Thomas P. Quinn, Michael J. Welch, and Jason S. Lewis
pp 2985–2992Publication Date (Web): March 08, 2005 (Article)
DOI: 10.1021/jm0490282
Conformationally Restricted Analogues of Psorospermin: Design, Synthesis, and Bioactivity of Natural-Product-Related Bisfuranoxanthones
Robert A. Heald, Thomas S. Dexheimer, Hariprasad Vankayalapati, Adam Siddiqui-Jain, Lajos Z. Szabo, Mary C. Gleason-Guzman, and Laurence H. Hurley
pp 2993–3004Publication Date (Web): March 16, 2005 (Article)
DOI: 10.1021/jm049299c
Applying Linear Interaction Energy Method for Rational Design of Noncompetitive Allosteric Inhibitors of the Sarco- and Endoplasmic Reticulum Calcium-ATPase
Pratap Singh, Anastasiah M. Mhaka, Soren B. Christensen, Jeffrey J. Gray, Samuel R. Denmeade, and John T. Isaacs
pp 3005–3014Publication Date (Web): March 16, 2005 (Article)
DOI: 10.1021/jm049319a
Additivity of Molecular Fields: CoMFA Study on Dual Activators of PPARα and PPARγ
Smriti Khanna, M. E. Sobhia, and Prasad V. Bharatam
pp 3015–3025Publication Date (Web): March 18, 2005 (Article)
DOI: 10.1021/jm049383s
Novel Cyclopropyl β-Amino Acid Analogues of Pregabalin and Gabapentin That Target the α2-δ Protein
Jacob B. Schwarz, Sian E. Gibbons, Shelley R. Graham, Norman L. Colbry, Peter R. Guzzo, Van-Duc Le, Mark G. Vartanian, Jack J. Kinsora, Susan M. Lotarski, Zheng Li, Melvin R. Dickerson, Ti-Zhi Su, Mark L. Weber, Ayman El-Kattan, Andrew J. Thorpe, Sean D. Donevan, Charles P. Taylor, and David J. Wustrow
pp 3026–3035Publication Date (Web): March 29, 2005 (Article)
DOI: 10.1021/jm0491086
Differential Inhibition of HIV-1 and SIV Envelope-Mediated Cell Fusion by C34 Peptides Derived from the C-Terminal Heptad Repeat of gp41 from Diverse Strains of HIV-1, HIV-2, and SIV
Elena Gustchina, Gerhard Hummer, Carole A. Bewley, and G. Marius Clore
pp 3036–3044Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jm049026h
Combinatorial Optimization of Isatin-β-Thiosemicarbazones as Anti-poxvirus Agents
Michael C. Pirrung, Sunil V. Pansare, Koushik Das Sarma, Kathy A. Keith, and Earl R. Kern
pp 3045–3050Publication Date (Web): March 30, 2005 (Article)
DOI: 10.1021/jm049147h
Neurosteroid Analogues. 10. The Effect of Methyl Group Substitution at the C-6 and C-7 Positions on the GABA Modulatory and Anesthetic Actions of (3α,5α)- and (3α,5β)-3-Hydroxypregnan-20-one
Chun-min Zeng, Brad D. Manion, Ann Benz, Alex S. Evers, Charles F. Zorumski, Steven Mennerick, and Douglas F. Covey
pp 3051–3059Publication Date (Web): March 25, 2005 (Article)
DOI: 10.1021/jm049027+
Structure−Activity Relationships of the Unique and Potent Agouti-Related Protein (AGRP)−Melanocortin Chimeric Tyr-c[β-Asp-His-DPhe-Arg-Trp-Asn-Ala-Phe-Dpr]-Tyr-NH2 Peptide Template
Andrzej Wilczynski, Krista R. Wilson, Joseph W. Scott, Arthur S. Edison, and Carrie Haskell-Luevano
pp 3060–3075Publication Date (Web): March 26, 2005 (Article)
DOI: 10.1021/jm049010r
Brief Articles
Synthesis and Structure−Activity Relationship of Fluoro Analogues of 8-{2-[4-(4-Methoxyphenyl)piperazin-1yl]ethyl}-8-azaspiro[4.5]decane-7,9-dione as Selective α1d-Adrenergic Receptor Antagonists
Michael J. Konkel, John M. Wetzel, Marie Cahir, Douglas A. Craig, Stewart A. Noble, and Charles Gluchowski
pp 3076–3079Publication Date (Web): March 30, 2005 (Brief Article)
DOI: 10.1021/jm0491391
Potent and Selective Aurora Inhibitors Identified by the Expansion of a Novel Scaffold for Protein Kinase Inhibition
Daniele Fancelli, Daniela Berta, Simona Bindi, Alexander Cameron, Paolo Cappella, Patrizia Carpinelli, Cornel Catana, Barbara Forte, Patrizia Giordano, Maria Laura Giorgini, Sergio Mantegani, Aurelio Marsiglio, Maurizio Meroni, Juergen Moll, Valeria Pittalà, Fulvia Roletto, Dino Severino, Chiara Soncini, Paola Storici, Roberto Tonani, Mario Varasi, Anna Vulpetti, and Paola Vianello
pp 3080–3084Publication Date (Web): March 10, 2005 (Brief Article)
DOI: 10.1021/jm049076m
Potential Antitumor Agents. 37.1 Synthesis and Antitumor Activity of Guanylhydrazones from Imidazo[2,1-b]thiazoles and from the New Heterocyclic System Thiazolo[2‘,3‘:2,3]imidazo[4,5-c]quinoline
Aldo Andreani, Massimiliano Granaiola, Alberto Leoni, Alessandra Locatelli, Rita Morigi, Mirella Rambaldi, Giorgio Lenaz, Romana Fato, Christian Bergamini, and Giovanna Farruggia
pp 3085–3089Publication Date (Web): March 18, 2005 (Brief Article)
DOI: 10.1021/jm040888s
Book Reviews
Pseudo-Peptides in Drug Discovery Edited by Peter E. Nielsen. Wiley-VCH, Weinheim, Germany. 2004. xiii + 244 pp. 17.5 × 24.5 cm. ISBN 3527306331. $125.00.
Victor J. Hruby
pp 3090–3091Publication Date (Web): March 11, 2005 (Book Review)
DOI: 10.1021/jm0581765
Oligonucleotide Synthesis. Methods and Applications Edited by Piet Herdewijn. Humana Press, Totowa, NJ. 2004. xi + 435 pp. 15.5 × 23.5 cm. ISBN 1-588-29-233-9. $125.00.
Stanley Crooke
p 3090Publication Date (Web): March 03, 2005 (Book Review)
DOI: 10.1021/jm058178p
Carbonic Anhydrase. Its Inhibitors and Activators. CRC Enzyme Inhibitors Series Edited by Claudiu T. Supuran, Andrea Scozzafava, and Janet Conway. CRC Press, Boca Rotan, FL. 2004. ix + 363 pp. 16 × 23 cm. ISBN 0-415-30673-6. $138.95.
Peter J. Harvison
p 3091Publication Date (Web): March 29, 2005 (Book Review)
DOI: 10.1021/jm058187y
Annual Review of Biochemistry. Volume 73 Edited by Charles C. Richardson, Roger D. Komrnberg, Christian R. H. Raetz, and Jeremy W. Thomrner. Annual Reviews, Palo Alto, CA. 2004. x + 1232 pp. 16 × 23.5 cm. ISBN 0-8243-0873-5. $84.00.
Thomas E. Prisinzano
pp 3091–3092Publication Date (Web): March 24, 2005 (Book Review)
DOI: 10.1021/jm058195e
Carbocation Chemistry Edited by George A. Olah and G. K. Surya Prakash. Wiley Interscience, New York. 2004. x + 393 pp. 16 × 24 cm. ISBN 041284904. $99.95.
Thomas J. Caggiano
p 3092Publication Date (Web): March 19, 2005 (Book Review)
DOI: 10.1021/jm0581922
Enzymes and Their Inhibition. Drug Development Edited by H. John Smith and Claire Simons. CRC Press, Boca Raton, FL. 2005. xi + 308 pp. 16 × 24 cm. ISBN 0-4153-3402-0. £85.00.
James Stivers
pp 3092–3093Publication Date (Web): March 22, 2005 (Book Review)
DOI: 10.1021/jm0581967
Make Your Mark in Science By Claus Ascheron and Angela Kickuth. Wiley, Hoboken, NJ. 2005. xiii + 235 pp. 14 × 20.5 cm. ISBN 0-471- 65733-6 (Paperback). $29.95.
Manfred E. Wolff
p 3093Publication Date (Web): March 29, 2005 (Book Review)
DOI: 10.1021/jm0582017
Additions and Corrections
Optically Active Mexiletine Analogues as Stereoselective Blockers of Voltage-Gated Na+ Channels.
Carlo Franchini, Alessia Carocci, Alessia Catalano, Maria M. Cavalluzzi, Filomena Corbo, Giovanni Lentini, Antonio Scilimati, Paolo Tortorella, Diana Conte Camerino, and Annamaria De Luca:
p 3094Publication Date (Web): March 16, 2005 (Addition/Correction)
DOI: 10.1021/jm0580048