Table of Contents

November 17, 2005
Volume 48, Issue 23
Pages 7089-7502

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).

Letters

7-(1,1-Dimethylethyl)-6-(2-ethyl-2H-1,2,4- triazol-3-ylmethoxy)-3-(2-fluorophenyl)- 1,2,4-triazolo[4,3-b]pyridazine:  A Functionally Selective γ-Aminobutyric AcidA (GABAA) α2/α3-Subtype Selective Agonist That Exhibits Potent Anxiolytic Activity but Is Not Sedating in Animal Models

pp 7089–7092
Publication Date (Web): October 14, 2005 (Letter)
DOI: 10.1021/jm058034a

Synthesis and Characterization of the Novel Fluorescent Prolyl Oligopeptidase Inhibitor 4-Fluoresceinthiocarbamoyl- 6-aminocaproyl-l-prolyl-2(S)-(Hydroxy- acetyl)pyrrolidine

pp 7093–7095
Publication Date (Web): October 20, 2005 (Letter)
DOI: 10.1021/jm0509187

Identification of Novel and Improved Antimitotic Agents Derived from Noscapine

pp 7096–7098
Publication Date (Web): October 13, 2005 (Letter)
DOI: 10.1021/jm050674q

SAR by MS:  Discovery of a New Class of RNA-Binding Small Molecules for the Hepatitis C Virus:  Internal Ribosome Entry Site IIA Subdomain

pp 7099–7102
Publication Date (Web): October 19, 2005 (Letter)
DOI: 10.1021/jm050815o

Articles

SAR and 3D-QSAR Studies on Thiadiazolidinone Derivatives:  Exploration of Structural Requirements for Glycogen Synthase Kinase 3 Inhibitors

pp 7103–7112
Publication Date (Web): October 08, 2005 (Article)
DOI: 10.1021/jm040895g

Synthesis, Molecular Modeling Studies, and Selective Inhibitory Activity against Monoamine Oxidase of 1-Thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole Derivatives

pp 7113–7122
Publication Date (Web): October 20, 2005 (Article)
DOI: 10.1021/jm040903t

Novel Tetralone-Derived Retinoic Acid Metabolism Blocking Agents:  Synthesis and in Vitro Evaluation with Liver Microsomal and MCF-7 CYP26A1 Cell Assays

pp 7123–7131
Publication Date (Web): October 21, 2005 (Article)
DOI: 10.1021/jm0501681

[N-Ethyl- and [N,N‘-Diethyl-1,2-bis(2,6-difluoro-3-hydroxyphenyl)- ethylenediamine]dichloroplatinum(II):  Structure and Cytotoxic/Estrogenic Activity in Breast Cancer Cells

pp 7132–7144
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm050186i

Ligand Docking in the Gastric H+/K+-ATPase:  Homology Modeling of Reversible Inhibitor Binding Sites

pp 7145–7152
Publication Date (Web): October 20, 2005 (Article)
DOI: 10.1021/jm050326o

Specific Targeting Highly Conserved Residues in the HIV-1 Reverse Transcriptase Primer Grip Region. Design, Synthesis, and Biological Evaluation of Novel, Potent, and Broad Spectrum NNRTIs with Antiviral Activity

pp 7153–7165
Publication Date (Web): October 25, 2005 (Article)
DOI: 10.1021/jm050257d

Virtual Screening of Novel CB2 Ligands Using a Comparative Model of the Human Cannabinoid CB2 Receptor

pp 7166–7171
Publication Date (Web): October 18, 2005 (Article)
DOI: 10.1021/jm050565b

Synthesis and 3D QSAR of New Pyrazolo[3,4-b]pyridines:  Potent and Selective Inhibitors of A1 Adenosine Receptors

pp 7172–7185
Publication Date (Web): October 15, 2005 (Article)
DOI: 10.1021/jm050407k

Benzophenone-Based Farnesyltransferase Inhibitors with High Activity against Trypanosoma cruzi

pp 7186–7191
Publication Date (Web): October 20, 2005 (Article)
DOI: 10.1021/jm050456x

In Vitro Anticancer Activities and Optical Imaging of Novel Intercalative Non-Cisplatin Conjugates

pp 7192–7197
Publication Date (Web): October 25, 2005 (Article)
DOI: 10.1021/jm050497t

Antitumor Polycyclic Acridines. 17.1 Synthesis and Pharmaceutical Profiles of Pentacyclic Acridinium Salts Designed To Destabilize Telomeric Integrity

pp 7198–7207
Publication Date (Web): October 15, 2005 (Article)
DOI: 10.1021/jm058031y

Some Insights into the Stereochemistry of Inhibition of Macrophage Migration Inhibitory Factor with 2-Fluoro-p-hydroxycinnamate and Its Analogues from Molecular Dynamics Simulations

pp 7208–7214
Publication Date (Web): October 13, 2005 (Article)
DOI: 10.1021/jm050562z

Synthesis of N-{4-[(2,4-Diamino-5-methyl-4,7-dihydro-3H- pyrrolo[2,3-d]pyrimidin-6-yl)thio]benzoyl}-l-glutamic Acid and N-{4-[(2-Amino-4-oxo-5-methyl-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin- 6-yl)thio]benzoyl}-l-glutamic Acid as Dual Inhibitors of Dihydrofolate Reductase and Thymidylate Synthase and as Potential Antitumor Agents

pp 7215–7222
Publication Date (Web): October 19, 2005 (Article)
DOI: 10.1021/jm058234m

Design, Synthesis, and Biological Evaluation of Dual Binding Site Acetylcholinesterase Inhibitors:  New Disease-Modifying Agents for Alzheimer's Disease

pp 7223–7233
Publication Date (Web): October 13, 2005 (Article)
DOI: 10.1021/jm0503289

Cellular Apoptosis and Cytotoxicity of Phenolic Compounds:  A Quantitative Structure−Activity Relationship Study

pp 7234–7242
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm050567w

Structural, Mutagenic, and Kinetic Analysis of the Binding of Substrates and Inhibitors of Human Phenylethanolamine N-Methyltransferase

pp 7243–7252
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm050568o

Radioiodinated Flavones for in Vivo Imaging of β-Amyloid Plaques in the Brain

pp 7253–7260
Publication Date (Web): October 19, 2005 (Article)
DOI: 10.1021/jm050635e

Synthesis and Evaluation of Estrogen Receptor Ligands with Bridged Oxabicyclic Cores Containing a Diarylethylene Motif:  Estrogen Antagonists of Unusual Structure

pp 7261–7274
Publication Date (Web): October 18, 2005 (Article)
DOI: 10.1021/jm0506773

Piperazinobenzopyranones and Phenalkylaminobenzopyranones:  Potent Inhibitors of Breast Cancer Resistance Protein (ABCG2)

pp 7275–7281
Publication Date (Web): October 25, 2005 (Article)
DOI: 10.1021/jm050705h

Enantioselective Nonsteroidal Aromatase Inhibitors Identified through a Multidisciplinary Medicinal Chemistry Approach

pp 7282–7289
Publication Date (Web): October 15, 2005 (Article)
DOI: 10.1021/jm058042r

Urotensin-II Receptor Ligands. From Agonist to Antagonist Activity

pp 7290–7297
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm058043j

Light-Induced Anticancer Activity of [RuCl2(DMSO)4] Complexes

pp 7298–7304
Publication Date (Web): October 19, 2005 (Article)
DOI: 10.1021/jm0502992

Synthesis and Biological Activity of Anticancer Ether Lipids That Are Specifically Released by Phospholipase A2 in Tumor Tissue

pp 7305–7314
Publication Date (Web): October 26, 2005 (Article)
DOI: 10.1021/jm049006f

Synthesis and Evaluation of Quindoline Derivatives as G-Quadruplex Inducing and Stabilizing Ligands and Potential Inhibitors of Telomerase

pp 7315–7321
Publication Date (Web): October 15, 2005 (Article)
DOI: 10.1021/jm050041b

Application of Validated QSAR Models of D1 Dopaminergic Antagonists for Database Mining

pp 7322–7332
Publication Date (Web): October 13, 2005 (Article)
DOI: 10.1021/jm049116m

Inhibitors of Tripeptidyl Peptidase II. 3. Derivation of Butabindide by Successive Structure Optimizations Leading to a Potential General Approach to Designing Exopeptidase Inhibitors

pp 7333–7342
Publication Date (Web): October 13, 2005 (Article)
DOI: 10.1021/jm0500830

Design, Synthesis, and Binding Studies of New Potent Ligands of Cannabinoid Receptors

pp 7343–7350
Publication Date (Web): October 13, 2005 (Article)
DOI: 10.1021/jm0501533

Tricyclic Pyrazoles. 3. Synthesis, Biological Evaluation, and Molecular Modeling of Analogues of the Cannabinoid Antagonist 8-Chloro-1-(2‘,4‘-dichlorophenyl)-N-piperidin-1-yl-1,4,5,6- tetrahydrobenzo[6,7]cyclohepta[1,2-c]pyrazole-3-carboxamide

pp 7351–7362
Publication Date (Web): October 19, 2005 (Article)
DOI: 10.1021/jm050317f

Novel Benzopyridothiadiazepines as Potential Active Antitumor Agents

pp 7363–7373
Publication Date (Web): October 25, 2005 (Article)
DOI: 10.1021/jm0503897

Structure−Activity Relationship of Triazafluorenone Derivatives as Potent and Selective mGluR1 Antagonists

pp 7374–7388
Publication Date (Web): October 21, 2005 (Article)
DOI: 10.1021/jm0504407

Δ9-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ9-Tetrahydrocannabinol

pp 7389–7399
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm050442r

Irreversible Inactivation of Trypanothione Reductase by Unsaturated Mannich Bases:  A Divinyl Ketone as Key Intermediate

pp 7400–7410
Publication Date (Web): October 13, 2005 (Article)
DOI: 10.1021/jm0504860

Damicoside from Axinella damicornis:  The Influence of a Glycosylated Galactose 4-OH Group on the Immunostimulatory Activity of α-Galactoglycosphingolipids

pp 7411–7417
Publication Date (Web): October 15, 2005 (Article)
DOI: 10.1021/jm050506y

Analysis of Peptide−Protein Binding Using Amino Acid Descriptors:  Prediction and Experimental Verification for Human Histocompatibility Complex HLA-A*0201

pp 7418–7425
Publication Date (Web): October 22, 2005 (Article)
DOI: 10.1021/jm0505258

Exploratory Chemistry toward the Identification of a New Class of Multidrug Resistance Reverters Inspired by Pervilleine and Verapamil Models

pp 7426–7436
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm050542x

Synthesis and Monoamine Transporter Binding Properties of 2,3-Diaryltropanes

pp 7437–7444
Publication Date (Web): October 21, 2005 (Article)
DOI: 10.1021/jm0582423

Anilinodialkoxyquinazolines:  Screening Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitors for Potential Tumor Imaging Probes

pp 7445–7456
Publication Date (Web): October 20, 2005 (Article)
DOI: 10.1021/jm050607w

Discovery of Novel and Potent Small-Molecule Inhibitors of NO and Cytokine Production as Antisepsis Agents:  Synthesis and Biological Activity of Alkyl 6-(N-Substituted sulfamoyl)cyclohex-1-ene-1-carboxylate

pp 7457–7467
Publication Date (Web): October 14, 2005 (Article)
DOI: 10.1021/jm050623t

Identification of Borinic Esters as Inhibitors of Bacterial Cell Growth and Bacterial Methyltransferases, CcrM and MenH

pp 7468–7476
Publication Date (Web): October 26, 2005 (Article)
DOI: 10.1021/jm050676a

Brief Articles

Statistical Tools for Virtual Screening

pp 7477–7481
Publication Date (Web): October 25, 2005 (Brief Article)
DOI: 10.1021/jm0501026

Synthesis of Two 3,5-Disubstituted Sulfonamide Catechol Ligands and Evaluation of Their Iron(III) Complexes for Use as MRI Contrast Agents

pp 7482–7485
Publication Date (Web): October 20, 2005 (Brief Article)
DOI: 10.1021/jm0501984

1-Benzhydryl-3-phenylurea and 1-Benzhydryl-3-phenylthiourea Derivatives:  New Templates among the CB1 Cannabinoid Receptor Inverse Agonists

pp 7486–7490
Publication Date (Web): October 21, 2005 (Brief Article)
DOI: 10.1021/jm0503906

Synthesis and Pharmacological Characterization of exo-2-(2‘-Chloro-5-pyridinyl)-7-(endo and exo)-aminobicyclo[2.2.1]heptanes as Novel Epibatidine Analogues

pp 7491–7495
Publication Date (Web): October 19, 2005 (Brief Article)
DOI: 10.1021/jm058243v

Random Chemistry as a New Tool for the Generation of Small Compound Libraries:  Development of a New Acetylcholinesterase Inhibitor

pp 7496–7499
Publication Date (Web): October 14, 2005 (Brief Article)
DOI: 10.1021/jm058041z

Book Reviews

Drug Discovery Handbook Edited by Shayne Cox Gad. Wiley-Interscience, Hoboken, NJ. 2005. xix + 1471 pp. 16 × 24 cm. ISBN 0471213845. $160.00.

p 7500
Publication Date (Web): October 14, 2005 (Book Review)
DOI: 10.1021/jm0582672

Annual Review of Biochemistry. Volume 74 Edited by Roger D. Kornberg, Christian R. H. Raetz, James E. Rothman, and Jeremy W. Thorner. Annual Reviews, Palo Alto, CA. 2005. x + 1010 pp. 15 × 25 cm. ISBN 0-8243-0874-3. $88.00.

pp 7500–7501
Publication Date (Web): October 14, 2005 (Book Review)
DOI: 10.1021/jm058268u

Frontiers in Natural Products Chemistry. Volume 1 Edited by Atta-ur-Rahman, M. Iqbal Choudhary, and Khalid M. Khan. Bentham Science Publishers, Ltd., Hilversum, The Netherlands. 2005. xiii + 234 pp. 16.5 × 25 cm. ISBN 90-77527-044. $130.00.

p 7501
Publication Date (Web): October 18, 2005 (Book Review)
DOI: 10.1021/jm058269m

Additions and Corrections

Determinants of Corticotropin Releasing Factor. Receptor Selectivity of Corticotropin Releasing Factor Related Peptides.

p 7502
Publication Date (Web): November 10, 2005 (Addition/Correction)
DOI: 10.1021/jm058274q