ChemMedChem

Cover image for Vol. 6 Issue 2

Special Issue: Rare & Neglected Diseases

February 7, 2011

Volume 6, Issue 2

Pages 209–379

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Cover Picture: Synthesis and Evaluation of Indatraline-Based Inhibitors for Trypanothione Reductase / Design, Synthesis and Biological Evaluation of Novel Inhibitors of Trypanosoma brucei Pteridine Reductase 1 / Modified 5′-Trityl Nucleosides as Inhibitors of Plasmodium falciparum dUTPase (ChemMedChem 2/2011) (page 209)

      Dr. Jeffrey G. A. Walton, Dr. Deuan C. Jones, Dr. Paula Kiuru, Dr. Alastair J. Durie, Dr. Nicholas J. Westwood, Prof. Alan H. Fairlamb, Daniel Spinks, Dr. Han B. Ong, Dr. Chidochangu P. Mpamhanga, Dr. Emma J. Shanks, Dr. David A. Robinson, Iain T. Collie, Dr. Kevin D. Read, Prof. Julie A. Frearson, Prof. Paul G. Wyatt, Dr. Ruth Brenk, Prof. Alan H. Fairlamb, Prof. Ian H. Gilbert, Dr. Gian Filippo Ruda, Dr. Corinne Nguyen, Dr. Przemysław Ziemkowski, Dr. Krzysztof Felczak, Dr. Ganasan Kasinathan, Alexander Musso-Buendia, Christian Sund, Xiao Xiong Zhou, Marcel Kaiser, Prof. Luis M. Ruiz-Pérez, Dr. Reto Brun, Prof. Tadeusz Kulikowski, Dr. Nils Gunnar Johansson, Prof. Dolores González-Pacanowska and Prof. Ian H. Gilbert

      Version of Record online: 28 JAN 2011 | DOI: 10.1002/cmdc.201190000

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      Better and safer drugs are required for neglected tropical diseases, such as malaria and the trypanosomatid diseases, human African trypanosomiasis, Chagas disease and leishmaniasis. However, these are “diseases of poverty” and therefore not economically viable for pharmaceutical companies to invest in at the early stage of drug discovery. For this reason, research conducted in an academic and nonprofit setting is of particular importance in filling this critical gap.

      The cover picture shows inhibitors of a drug target in malaria (dUTPase, upper right) and two enzyme targets common to the trypanosomatid diseases (trypanothione reductase, lower left; pteridine reductase 1, lower right). The cover also shows a transmission electron micrograph (upper left) of a late trophozoite stage of a malaria parasite (cyan) infecting an erythrocyte (magenta), and a scanning electron micrograph of a bloodstream form of the African trypanosome (bottom centre). For more details, see the Full Papers by Nicholas J. Westwood, Alan H. Fairlamb et al. (p. 321 ff), and Ian H. Gilbert et al. (p. 302 ff and p. 309 ff).

  2. Inside Cover

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Inside Cover: Combating Cystic Fibrosis: In Search for CF Transmembrane Conductance Regulator (CFTR) Modulators / Second-Generation Iminoxylitol-Based Pharmacological Chaperones for the Treatment of Gaucher Disease (ChemMedChem 2/2011) (page 210)

      Dr. Efrat Noy, Prof. Hanoch Senderowitz, Farah Oulaïdi, Sophie Front-Deschamps, Dr. Estelle Gallienne, Dr. Eric Lesellier, Kyoko Ikeda, Dr. Naoki Asano, Prof. Philippe Compain and Prof. Olivier R. Martin

      Version of Record online: 28 JAN 2011 | DOI: 10.1002/cmdc.201190001

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      The inside cover picture shows a model of cystic fibrosis transmembrane conductance regulator (CFTR; right); such structural information can be used to develop CFTR modulators for the treatment of CF. On the left, simplified iminoglycolipids can be designed without loss of potency against glucocerebrosidase (GCase), the enzyme responsible for Gaucher disease (β-GCase image adapted from A. H. Futerman, Trends Pharmacol. Sci. 2004, 25, 147). For more information, see the Minireview by Hanoch Senderowitz et al. (p. 243 ff.) and the Full Paper by Philippe Compain, Olivier R. Martin et al. (p. 353 ff.).

  3. Editorial

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. You have free access to this content
      Location, Location, Location (pages 211–213)

      Prof. Alan Kozikowski and Prof. Maurizio Botta

      Version of Record online: 28 JAN 2011 | DOI: 10.1002/cmdc.200000528

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. You have free access to this content
  5. News

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
  6. Author Profile

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Maurizio Botta (page 227)

      Version of Record online: 17 JAN 2011 | DOI: 10.1002/cmdc.201000500

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      What is the secret to publishing high-quality papers? Well-trained, highly motivated, trustworthy collaborators. The most significant scientific advance in drug discovery of the last 100 years has been … the development of molecular modeling techniques. This and more about Maurizio Botta can be found on page 227.

  7. Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
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    1. Allosteric Inhibitor Development Targeting HIV-1 Integrase (pages 228–241)

      Laith Q. Al-Mawsawi and Nouri Neamati

      Version of Record online: 12 JAN 2011 | DOI: 10.1002/cmdc.201000443

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      See you on the other site: HIV-1 integrase (IN) is quite amenable to the development of allosteric inhibitors, as there are many ways to block this enzyme's function in vivo. We discuss the approaches that have been taken toward inhibiting IN function without directly targeting the catalytic site; this strategy is central in pharmacological efforts to stay one step ahead of emerging IN-drug-resistant HIV strains.

  8. Minireview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Combating Cystic Fibrosis: In Search for CF Transmembrane Conductance Regulator (CFTR) Modulators (pages 243–251)

      Dr. Efrat Noy and Prof. Hanoch Senderowitz

      Version of Record online: 14 JAN 2011 | DOI: 10.1002/cmdc.201000488

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      Open sesame! Compounds that correct the folding, trafficking and gating defects in cystic fibrosis transmembrane conductance regulator (CFTR), the main protein implicated in cystic fibrosis (CF), are of great interest as potential therapeutic agents for this lethal disease. The development of CFTR modulators, highlighting the main challenges in the field and advocating the application of rational rather than brute-force methods, is the focus of this Minireview.

  9. Communications

    1. Top of page
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    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Strategies towards Improving the Pharmacokinetic Profile of ε-Substituted Lysinol-Derived HIV Protease Inhibitors (pages 253–257)

      Dr. Hemaka A. Rajapakse, Dr. Abbas M. Walji, Keith P. Moore, Hong Zhu, Aurpon W. Mitra, Alison R. Gregro, Elizabeth Tinney, Christine Burlein, Sinoeun Touch, Brenda L. Paton, Dr. Steven S. Carroll, Dr. Daniel J. DiStefano, Dr. Ming-Tain Lai, Dr. Jay A. Grobler, Dr. Rosa I. Sanchez, Dr. Theresa M. Williams, Dr. Joseph P. Vacca and Dr. Philippe G. Nantermet

      Version of Record online: 29 DEC 2010 | DOI: 10.1002/cmdc.201000395

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      Compounds that are all HAART: Subsequent to accessing the S2 subpocket of HIV protease from the novel lysinol series of HIV protease inhibitors, we now report a comprehensive structure–activity relationship study at this position. Balancing physical properties via truncation of the substituent binding in the S1′ subpocket enabled the discovery of inhibitors with improved pharmacokinetic properties, while maintaining the functional potency of these inhibitors.

    2. Fragment-Based Design of Ligands Targeting a Novel Site on the Integrase Enzyme of Human Immunodeficiency Virus 1 (pages 258–261)

      Dr. Jerome Wielens, Dr. Stephen J. Headey, Dr. John J. Deadman, Dr. David I. Rhodes, Prof. Michael W. Parker, Dr. David K. Chalmers and Prof. Martin J. Scanlon

      Version of Record online: 16 DEC 2010 | DOI: 10.1002/cmdc.201000483

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      Every little bit counts! Fragment-based screening has been used to identify a novel ligand binding site on HIV-1 integrase. Crystal structures of fragments bound at this site (shown) have been used to design elaborated second- generation compounds that bind with higher affinity and good ligand efficiency.

    3. Synthesis and Evaluation of Potent Ene–yne Inhibitors of Type II Dehydroquinases as Tuberculosis Drug Leads (pages 262–265)

      Anh Thu Tran, Dr. Katie M. Cergol, Dr. Nicholas P. West, Elizabeth J. Randall, Prof. Warwick J. Britton, Syed Ali Imran Bokhari, Musadiq Ibrahim, Dr. Adrian J. Lapthorn and Dr. Richard J. Payne

      Version of Record online: 4 NOV 2010 | DOI: 10.1002/cmdc.201000399

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      E-9: You sunk my battleship! Potent ene–yne-based inhibitors of type II dehydroquinase are described. The majority of the compounds exhibited nanomolar inhibition of the Streptomyces coelicolor, Helicobacter pylori and Mycobacterium tuberculosis type II dehydroquinases. The inhibitors also possessed moderate activity against the growth of M. tuberculosis in vitro.

    4. Tetrahydrobenzothiophene Derivatives: Conformationally Restricted Inhibitors of Type II Dehydroquinase (pages 266–272)

      Sonia Paz, Lorena Tizón, Dr. José M. Otero, Dr. Antonio L. Llamas-Saiz, Dr. Gavin C. Fox, Dr. Mark J. van Raaij, Dr. Heather Lamb, Prof. Dr. Alastair R. Hawkins, Dr. Adrian J. Lapthorn, Prof. Dr. Luis Castedo and Prof. Dr. Concepción González-Bello

      Version of Record online: 10 NOV 2010 | DOI: 10.1002/cmdc.201000343

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      Restriction is good for inhibition! Tetrahydrobenzothiophene-derived rigid mimics of the type II dehydroquinase (DHQ2)-catalyzed reaction intermediate are reported. These derivatives fix the interaction with the tyrosine, the base that initiates the enzymatic reaction, in an inappropriate orientation for catalysis. Two competitive inhibitors in the series, 2-propenyl derivative 5 e and 2-cyclopropylethyl compound 5 i (shown), were crystallized in complex with DHQ2 from Helicobacter pylori, and the X-ray structures were determined at 1.95 Å and 1.85 Å, respectively.

    5. Potent and Selective Inhibition of Cysteine Proteases from Plasmodium falciparum and Trypanosoma brucei (pages 273–278)

      Veronika Ehmke, Cornelia Heindl, Dr. Matthias Rottmann, Céline Freymond, Dr. W. Bernd Schweizer, Prof. Dr. Reto Brun, Dr. August Stich, Prof. Dr. Tanja Schirmeister and Prof. Dr. François Diederich

      Version of Record online: 25 NOV 2010 | DOI: 10.1002/cmdc.201000449

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      Treating tropical diseases: Structure-based design afforded highly active triazine nitrile inhibitors of the protozoan cysteine proteases falcipain-2 and rhodesain. Optimization of the occupancy of the S1, S2, and S3 pockets of these enzymes yielded inhibitory constants in the low nanomolar activity range. The new ligands are selective against other related proteases and exhibit in vitro activities against the protozoan parasites.

  10. Full Papers

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Reactions of Antimalarial Peroxides with Each of Leucomethylene Blue and Dihydroflavins: Flavin Reductase and the Cofactor Model Exemplified (pages 279–291)

      Prof. Dr. Richard K. Haynes, Kwan-Wing Cheu, Maggie Mei-Ki Tang, Min-Jiao Chen, Dr. Zu-Feng Guo, Prof. Dr. Zhi-Hong Guo, Dr. Paolo Coghi and Prof. Dr. Diego Monti

      Version of Record online: 23 DEC 2010 | DOI: 10.1002/cmdc.201000508

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      Antimalarial peroxides and flavin reductase: NADPH–E. coli flavin reductase (Fre) reduces FAD to FADH2, which in turn rapidly reduces artemisinins and antimalarial peroxides to deoxy or ketone products under physiological conditions. Thus, antimalarial activity is due to perturbation of intraparasitic redox homeostasis by oxidation of FADH2 in critical flavoenzymes with consequent sequestration of NADPH. The tetraoxane uses both peroxide units in consuming two equivalents of NADPH in the NADPH–Fre–FAD system.

    2. Improved Inhibitors of Trypanothione Reductase by Combination of Motifs: Synthesis, Inhibitory Potency, Binding Mode, and Antiprotozoal Activities (pages 292–301)

      Christian Eberle, Birgit Sophia Lauber, Daniel Fankhauser, Marcel Kaiser, Prof. Dr. Reto Brun, Prof. Dr. R. Luise Krauth-Siegel and Prof. Dr. François Diederich

      Version of Record online: 16 DEC 2010 | DOI: 10.1002/cmdc.201000420

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      Parasites beware! Combination of trypanothione reductase (TR) inhibitor motifs, aided by computer-based design, led to selective compounds with Kic values as low as 0.51±0.1 μM. The majority of the newly prepared ligands exhibit low cytotoxicity and IC50 values between 0.12 and 6.0 μM against the protozoan parasites T. b. rhodesiense and P. falciparum.

    3. You have full text access to this OnlineOpen article
      Design, Synthesis and Biological Evaluation of Novel Inhibitors of Trypanosoma brucei Pteridine Reductase 1 (pages 302–308)

      Daniel Spinks, Dr. Han B. Ong, Dr. Chidochangu P. Mpamhanga, Dr. Emma J. Shanks, Dr. David A. Robinson, Iain T. Collie, Dr. Kevin D. Read, Prof. Julie A. Frearson, Prof. Paul G. Wyatt, Dr. Ruth Brenk, Prof. Alan H. Fairlamb and Prof. Ian H. Gilbert

      Version of Record online: 29 DEC 2010 | DOI: 10.1002/cmdc.201000450

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      Picking pockets for progressing potency! The optimisation of some hits for Trypanosoma brucei pteridine reductase 1 (PTR1) discovered through virtual screening (J. Med. Chem. 2009, 52, 4454) is described. We were able to derive potent competitive inhibitors of PTR1 (equation image=7 nM), which displayed weak activity against the parasites, probably due to accumulation of the dihydrobiopterin substrate displacing the inhibitor from PTR1.

    4. Modified 5′-Trityl Nucleosides as Inhibitors of Plasmodium falciparum dUTPase (pages 309–320)

      Dr. Gian Filippo Ruda, Dr. Corinne Nguyen, Dr. Przemysław Ziemkowski, Dr. Krzysztof Felczak, Dr. Ganasan Kasinathan, Alexander Musso-Buendia, Christian Sund, Xiao Xiong Zhou, Marcel Kaiser, Prof. Luis M. Ruiz-Pérez, Dr. Reto Brun, Prof. Tadeusz Kulikowski, Dr. Nils Gunnar Johansson, Prof. Dolores González-Pacanowska and Prof. Ian H. Gilbert

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/cmdc.201000445

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      Fewer trips to the dUMP: dUTPase is a potential drug target for the treatment of malaria. We previously reported the discovery of 5′-tritylated analogues of deoxyuridine as selective inhibitors of this P. falciparum enzyme. Herein we report further structure–activity studies of the 5′-trityl group, the introduction of various substituents at the 3′-position of deoxyuridine, and modifications of the base.

    5. You have full text access to this OnlineOpen article
      Synthesis and Evaluation of Indatraline-Based Inhibitors for Trypanothione Reductase (pages 321–328)

      Dr. Jeffrey G. A. Walton, Dr. Deuan C. Jones, Dr. Paula Kiuru, Dr. Alastair J. Durie, Dr. Nicholas J. Westwood and Prof. Alan H. Fairlamb

      Version of Record online: 15 DEC 2010 | DOI: 10.1002/cmdc.201000442

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      Give these inhibitors a TryR: Indatraline is a CNS-active inhibitor of trypanothione reductase (TryR) revealed in a previous high-throughput screen. For this study we prepared analogues of indatraline and tested their capacity to inhibit TryR and the proliferation of Trypanosoma brucei cells. Inhibitors of micromolar potency with a mixed mode of inhibition were identified.

    6. You have full text access to this OnlineOpen article
      Synthesis and in vitro/in vivo Evaluation of the Antitrypanosomal Activity of 3-Bromoacivicin, a Potent CTP Synthetase Inhibitor (pages 329–333)

      Prof. Paola Conti, Dr. Andrea Pinto, Dr. Pui E. Wong, Dr. Louise L. Major, Dr. Lucia Tamborini, Dr. Maria C. Iannuzzi, Prof. Carlo De Micheli, Prof. Michael P. Barrett and Dr. Terry K. Smith

      Version of Record online: 22 DEC 2010 | DOI: 10.1002/cmdc.201000417

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      A tip of the HAT to bromine: The antitrypanosomal activity of the natural antibiotic acivicin can be substantially increased on passing to its 3-bromo analogue. 3-Bromoacivicin is threefold more potent than acivicin as an inhibitor of T. b. brucei CTP synthetase. Interestingly, this translates into a 12-fold increase in the antitrypanosomal activity and a marked improvement in selectivity.

    7. Pyrido[1,2-a]benzimidazole-Based Agents Active Against Tuberculosis (TB), Multidrug-Resistant (MDR) TB and Extensively Drug-Resistant (XDR) TB (pages 334–342)

      Dr. Marco Pieroni, Dr. Suresh K. Tipparaju, Dr. Shichun Lun, Dr. Yang Song, A. Willem Sturm, Prof. Dr. William R. Bishai and Prof. Dr. Alan P. Kozikowski

      Version of Record online: 21 JAN 2011 | DOI: 10.1002/cmdc.201000490

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      Waging war on TB: Using high-throughput screening, we have identified a pyrido[1,2-a]benzimidazole as a potent antitubercular agents. Chemical modifications to the hit compound led to an analogue (3h) with improved potency and reduced toxicity. Of considerable interest was the finding that 3h maintained activity against two extensively drug-resistant strains and one multidrug-resistant strain of tuberculosis (TB). These compounds represent promising leads in the quest for improved anti-TB drugs.

    8. A Versatile and Practical Synthesis toward the Development of Novel HIV-1 Integrase Inhibitors (pages 343–352)

      Dr. Marta Rinaldi, Dr. Cristina Tintori, Dr. Luigi Franchi, Dr. Giulia Vignaroli, Dr. Anna Innitzer, Prof. Silvio Massa, Prof. José A. Esté, Dr. Encarna Gonzalo, Dr. Frauke Christ, Prof. Zeger Debyser and Prof. Maurizio Botta

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/cmdc.201000510

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      Easy as A, B, C: Three new series of salicylic acid derivatives were designed and synthesized to investigate their activity toward HIV-1 integrase. Some of these compounds were obtained with microwave-assisted procedures developed and optimized in our research group, which allowed us to rapidly generate several final compounds of high purity.

    9. Second-Generation Iminoxylitol-Based Pharmacological Chaperones for the Treatment of Gaucher Disease (pages 353–361)

      Farah Oulaïdi, Sophie Front-Deschamps, Dr. Estelle Gallienne, Dr. Eric Lesellier, Kyoko Ikeda, Dr. Naoki Asano, Prof. Philippe Compain and Prof. Olivier R. Martin

      Version of Record online: 4 JAN 2011 | DOI: 10.1002/cmdc.201000469

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      Simplify without sacrificing potency: Shifting the alkyl chain from the pseudo-anomeric position to O2 in iminoxylitol derivatives maintains high inhibitory potency toward glucosylceramidase as well as chaperone activity at sub-inhibitory concentration (10 nM). This structural simplification leads to shorter and more practical synthetic sequences.

    10. Synthesis and Antimicrobial Evaluation of Nitazoxanide-Based Analogues: Identification of Selective and Broad Spectrum Activity (pages 362–377)

      Dr. T. Eric Ballard, Xia Wang, Dr. Igor Olekhnovich, Taylor Koerner, Craig Seymour, Joseph Salamoun, Michelle Warthan, Prof. Paul S. Hoffman and Prof. Timothy L. Macdonald

      Version of Record online: 29 DEC 2010 | DOI: 10.1002/cmdc.201000475

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      Hitting them where it hurts! A library of nitazoxanide-based analogues was synthesized and assayed for antibacterial efficacy against pyruvate–ferredoxin oxidoreductase (PFOR) utilizing microorganisms. Derivatives were found to recapitulate and improve activity against these organisms, and select analogues were screened for activity against staphylococci resulting in the identification of analogues capable of inhibiting both staphylococci and all PFOR organisms at low micromolar minimum inhibitory concentrations.

  11. Book Review

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. GPCR Molecular Pharmacology and Drug Targeting. Edited by Annette Gilchrist. (page 378)

      Prof. Andrzej J. Bojarski

      Version of Record online: 4 NOV 2010 | DOI: 10.1002/cmdc.201000453

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      Wiley, Hoboken 2010. 536 pp., hardcover $ 149.95.—ISBN 978-0-470-30778-6

  12. Preview

    1. Top of page
    2. Cover Picture
    3. Inside Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Author Profile
    8. Review
    9. Minireview
    10. Communications
    11. Full Papers
    12. Book Review
    13. Preview
    1. Preview: ChemMedChem 3/2011 (page 379)

      Version of Record online: 28 JAN 2011 | DOI: 10.1002/cmdc.201190004

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