Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization

• Barry M. Trost,
• Michael C. Ryan and
• Meera Rao

Beilstein J. Org. Chem. 2016, 12, 1136–1152, doi:10.3762/bjoc.12.110

• molecular architectures hold a particular interest to the chemical community, especially in the fields of natural product synthesis and drug design, researchers have made a significant effort to discover asymmetric variations of enyne cycloisomerization reactions [11][12]. Researchers have used a variety of

Correction: Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 608–610, doi:10.3762/bjoc.12.59

• ; computational chemistry; drug design; molecular recognition; relaxed force constants; Our original publication contains an erratic number of predicted antibiotic structures in Scheme 2. With this Erratum we provide the corrected Scheme 2. Scheme 2 in the original article: Predicted new linezolid-like

Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 415–428, doi:10.3762/bjoc.12.45

• : compliance constants; computational chemistry; drug design; molecular recognition; relaxed force constants; Introduction Antibiotic resistance is one of the major health problems in modern societies, causing millions of deaths per year [1][2][3]. Although Alexander Fleming recognized the importance of the

• computer-based drug design was one of the big scientific promises. New drugs are nowadays produced at the same rate as they were 60 years ago [27], notwithstanding enormous investments and undeniable achievements both, in computer soft- and hardware. Modern computational drug design strategies range from A

Diversity-oriented synthesis of analogues of the novel macrocyclic peptide FR-225497 through late stage functionalization

• Jyotiprasad Mukherjee,
• Suman Sil and
• Shital Kumar Chattopadhyay

Beilstein J. Org. Chem. 2015, 11, 2487–2492, doi:10.3762/bjoc.11.270

• peptides of the general structure 1 (Figure 1) displays important histone deacetylase inhibition property relevant to drug design against a number of diseases ranging from antifungal, antimicrobial to arrest of proliferation of several cell types of epithelial and hematological origin [13]. The compounds

Influence of length and flexibility of spacers on the binding affinity of divalent ligands

• Susanne Liese and
• Roland R. Netz

Beilstein J. Org. Chem. 2015, 11, 804–816, doi:10.3762/bjoc.11.90

• ]. Also in drug design, the synthesis of artificial multivalent ligands is a promising route to increase the binding affinity or to reduce the amount of substance required for treatment [4][5][6][7]. The term multivalency is used for systems that consist of several identical binding partners. Thereby, the

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• , Germany 10.3762/bjoc.11.65 Abstract For antiviral drug design, especially in the field of influenza virus research, potent multivalent inhibitors raise high expectations for combating epidemics and pandemics. Among a large variety of covalent and non-covalent scaffold systems for a multivalent display of

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

• Radhey M. Singh,
• Kishor Chandra Bharadwaj and
• Dharmendra Kumar Tiwari

Beilstein J. Org. Chem. 2014, 10, 2975–2980, doi:10.3762/bjoc.10.315

• . This is especially relevant given the fact that they have been extensively used in drug design [23][24], polymer chemistry [25][26] and are popular synthetic templates [27][28]. For further comparison to other acryl systems, acrylamide also offers extra valencies at nitrogen, which can be used for

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• significantly smaller in size and hence, easier and cheaper to synthesize using chemical strategies [5]. Thereby, they provide a vast perspective for novel drug design. Table 1 summarizes valuable virtues and pivotal shortcomings of therapeutic peptides compared to traditional small organic molecules. The high

• SPPS for drug development The described method of chemical synthesis of peptides on the solid phase and particularly, its outstanding potential for automation, have led to routine methods in the development of novel pharmaceuticals. In principle, there are two approaches for drug design: rational and

Stereocontrolled synthesis of 5-azaspiro[2.3]hexane derivatives as conformationally “frozen” analogues of L-glutamic acid

• Beatrice Bechi,
• David Amantini,
• Cristina Tintori,
• Maurizio Botta and
• Romano di Fabio

Beilstein J. Org. Chem. 2014, 10, 1114–1120, doi:10.3762/bjoc.10.110

• Road, Manchester, M13 9PL, UK Neurosciences Centre of Excellence for Drug Discovery, GlaxoSmithKline Medicines Research Centre, Via A. Fleming 4, 37135, Verona, Italy Present address: Galapagos SASU, 102 avenue Gaston Roussel, 93230 Romainville, France Present address: Drug Design and Discovery, Aptuit

The total synthesis of D-chalcose and its C-3 epimer

• Jun Sun,
• Song Fan,
• Zhan Wang,
• Guoning Zhang,
• Kai Bao and
• Weige Zhang

Beilstein J. Org. Chem. 2013, 9, 2620–2624, doi:10.3762/bjoc.9.296

• Jun Sun Song Fan Zhan Wang Guoning Zhang Kai Bao Weige Zhang Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China Center for Molecular Imaging, Beth Israel Deaconess Medical Center, Harvard Medical School

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

The chemistry of isoindole natural products

• Klaus Speck and
• Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

• cellular signaling and their association with cancer, a tremendous effort in the development of selective protein kinase inhibitors was undertaken. This resulted in the discovery of the anticancer agent imatinib (Gleevec, 34) by rational drug design (Figure 4). Midostaurin (35), a semisynthetic derivative

Synthesis of the calcilytic ligand NPS 2143

• Henrik Johansson,
• Thomas Cailly,
• Alex Rojas Bie Thomsen,
• Hans Bräuner-Osborne and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2013, 9, 1383–1387, doi:10.3762/bjoc.9.154

• Henrik Johansson Thomas Cailly Alex Rojas Bie Thomsen Hans Brauner-Osborne Daniel Sejer Pedersen Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark Université de Caen Basse-Normandie, CERMN (EA 4258 - FR CNRS 3038 INC3M - SF 4206

Design and synthesis of tag-free photoprobes for the identification of the molecular target for CCG-1423, a novel inhibitor of the Rho/MKL1/SRF signaling pathway

• Jessica L. Bell,
• Andrew J. Haak,
• Susan M. Wade,
• Yihan Sun,
• Richard R. Neubig and
• Scott D. Larsen

Beilstein J. Org. Chem. 2013, 9, 966–973, doi:10.3762/bjoc.9.111

• the macromolecular target(s) of 1 would allow us to employ rational and structure-based drug design to create more potent and selective therapeutics for the treatment of RhoA-related disorders. Early efforts at optimization in our laboratory led to nipecotic (bis)amide analogue 2 (CCG-100602, Figure 1

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• prove to be efficacious in ALS patients. Various screening approaches and targeted drug design, as outlined in this review, have identified a number of small molecules that will prove useful in the discovery and validation of novel cellular targets for the treatment of ALS (Figure 15). Figure 15

Synthesis and stability study of a new major metabolite of γ-hydroxybutyric acid

• Ida Nymann Petersen,
• Jesper Langgaard Kristensen,
• Christian Tortzen,
• Torben Breindahl and
• Daniel Sejer Pedersen

Beilstein J. Org. Chem. 2013, 9, 641–646, doi:10.3762/bjoc.9.72

• Ida Nymann Petersen Jesper Langgaard Kristensen Christian Tortzen Torben Breindahl Daniel Sejer Pedersen Department of Drug Design and Pharmacology, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark Department of Chemistry, University of Copenhagen, Universitetsparken 5

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives

• Wentao Gao,
• Guihai Lin,
• Yang Li,
• Xiyue Tao,
• Rui Liu and
• Lianjie Sun

Beilstein J. Org. Chem. 2012, 8, 1849–1857, doi:10.3762/bjoc.8.213

• of the above findings as well as the combination principles for drug design [31], we were intrigued to explore the incorporation of a quinoline ring fused together with a benzoxepine nucleus, which would be much more attractive and valuable for medicinal chemistry and drug discovery. In recent years

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics

• Workalemahu M. Berhanu,
• Mohamed A. Ibrahim,
• Girinath G. Pillai,
• Alexander A. Oliferenko,
• Levan Khelashvili,
• Farukh Jabeen,
• Bushra Mirza,
• Farzana Latif Ansari,
• Ihsan ul-Haq,
• Said A. El-Feky and
• Alan R. Katritzky

Beilstein J. Org. Chem. 2012, 8, 1146–1160, doi:10.3762/bjoc.8.128

• affording opportunities for drug design and development. One strategy to create peptidomimetics couples a small-molecule scaffold with a peptide. Such scaffolds include aromatic rings or heterocycles, which may be positioned in the interior of the peptide chain [4][5] or at the C- [6][7][8] or N-terminus [9

• economic synthetic route, renders scaffold 37 as a promising platform for further rational drug design. Synthesis Treatment of dicarboxylic acids 34a–c by a standard method [36] using thionyl chloride and 1H-benzotriazole gave the corresponding benzotriazole derivatives in 37–54% yield (Scheme 1, see

Antibiotic and cytotoxic peptides

• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1144–1145, doi:10.3762/bjoc.8.127

• in Medicinal Chemistry [2]. This Thematic Series on “Antibiotic and cytotoxic peptides” presents contributions from synthetic chemists active in the fields of peptides, peptidomimetics, drug design, and method development, in order to promote the research area further and to disseminate the

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• structures for synthesis, or on glyco-enzymes that can be used to synthesize carbohydrates. Statistical analyses of glycan databases help to plan glycan synthesis experiments. 3D-Structural data of protein–carbohydrate complexes are used in targeted drug design, and tools to support glycan structure analysis

• DrawRings are used by some databases to enable graphical input of glycan (sub-)structure queries using icons to describe monosaccharides. Atomic pictograms as frequently used by chemists, however, are not supported by these tools. 3D Structure information for targeted drug design Knowledge of the 3D

Investigation of the network of preferred interactions in an artificial coiled-coil association using the peptide array technique

• Raheleh Rezaei Araghi,
• Carsten C. Mahrenholz,
• Rudolf Volkmer and
• Beate Koksch

Beilstein J. Org. Chem. 2012, 8, 640–649, doi:10.3762/bjoc.8.71

• the concept of rational drug design based on coiled-coil proteins [6]. In this context, the use of unnatural amino acids in peptidomimetics is advisable, to enhance enzymatic stability, limit conformational flexibility, and improve pharmacodynamics and bioavailability [7]. In order to manipulate helix

Synthesis of fluorinated maltose derivatives for monitoring protein interaction by ¹⁹F NMR

• Michaela Braitsch,
• Hanspeter Kählig,
• Georg Kontaxis,
• Michael Fischer,
• Toshinari Kawada,
• Robert Konrat and
• Walther Schmid

Beilstein J. Org. Chem. 2012, 8, 448–455, doi:10.3762/bjoc.8.51

• with efficient synthetic approaches to fluorinated derivatives, this offers exciting perspectives for rational programs for drug design. Experiments to explore these possibilities are currently underway in our laboratories. Applications of the reporter system to biological material inherently giving

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira–Glaser cyclization sequence

• Dominik Urselmann,
• Dragutin Antovic and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1499–1503, doi:10.3762/bjoc.7.174

• ; thiophenes; Introduction Over the past decades 2,5-di(hetero)aryl substituted thiophenes [1][2] have constantly attracted a lot of interest, especially as charge-transport materials in electronic [3] and optoelectronic [4][5][6] devices, but also in drug design as antitumor [7] or anti-inflammatory agents

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

• Bruno Linclau,
• Leo Leung,
• Jean Nonnenmacher and
• Graham Tizzard

Beilstein J. Org. Chem. 2010, 6, No. 62, doi:10.3762/bjoc.6.62

• well as the lipophilicity, chemical and metabolic stability of the compound. Recent exciting reports describe weak but stabilising interactions between a C–F moiety and protein residues, which is certain to have implications in drug design [2][3]. Further important applications include molecular

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32