Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase

• María Emilia Cano,
• Rosalía Agusti,
• Alejandro J. Cagnoni,
• María Florencia Tesoriero,
• José Kovensky,
• María Laura Uhrig and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324

• -acetyllactosamine was also evaluated. Results and Discussion As part of our project on the synthesis and biological evaluation of multivalent ligands, two families of mono- and divalent structures were synthesized in order to study their ability as acceptors or inhibitors of the reaction catalyzed by the T. cruzi

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions

• Alan M. Jones and
• Craig E. Banks

Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323

• also highlight new technologies and techniques applied to this area of electrosynthesis. We conclude with the use of this electrosynthetic approach to challenging syntheses of natural products and other complex structures for biological evaluation discussing recent technological developments in

Gold(I)-catalysed synthesis of a furan analogue of thiamine pyrophosphate

• Amjid Iqbal,
• El-Habib Sahraoui and
• Finian J. Leeper

Beilstein J. Org. Chem. 2014, 10, 2580–2585, doi:10.3762/bjoc.10.270

• over the triazole analogues that it can be functionalised at the C-2 position. Conclusion In conclusion, we report here the short synthesis of a furan analogue of thiamine, which could be diphosphorylated to give an analogue of ThDP. Biological evaluation of this diphosphate showed that it is a very

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

• Michail Syrpas,
• Ewout Ruysbergh,
• Christian V. Stevens,
• Norbert De Kimpe and
• Sven Mangelinckx

Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265

• compounds can be regarded as building blocks for further elaborations towards new analogues of AHLs. Therefore this study aimed towards the synthesis and biological evaluation of a series of novel halogenated analogues, in which a chlorine, bromine or iodine atom was introduced. To further evaluate the

• chlorinated AHL analogues 11a–f via reaction with S-homoserine lactone hydrobromide (1) and triethylamine (Scheme 3). Biological evaluation The above mentioned natural AHLs 3 and their halogenated analogues 6, 8 and 11 were first tested for their ability to induce fluorescence in the Escherichia coli JB523

• ), 2860 (CH), 2930 (CH), 2958 (CH), 3298 (NH); chromatography: EtOAc/PE 4:1 Rf 0.48; melting point: 144 °C; white powder; yield: 42%. Biological evaluation Escherichia coli JB523 green fluorescent protein (GFP) microplate assay Strain JB523 was grown overnight at 28 °C in Luria–Bertani (LB) medium

Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues

• Nadezhda V. Sokolova,
• Valentine G. Nenajdenko,
• Vladimir B. Sokolov,
• Daria V. Vinogradova,
• Elena F. Shevtsova,
• Ludmila G. Dubova and
• Sergey O. Bachurin

Beilstein J. Org. Chem. 2014, 10, 155–162, doi:10.3762/bjoc.10.13

• significant influence on mitochondrial swelling (data not shown). But at higher pharmacologically relevant concentration of 30 µM (60 nmol/mg mitochondria) all compounds did not affect the ΔΨm and increased the resistance of mitochondria to calcium-induced MPT (Table 2). The results of biological evaluation

Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

• John Li,
• May May Leong,
• Alastair Stewart and
• Mark A. Rizzacasa

Beilstein J. Org. Chem. 2013, 9, 2762–2766, doi:10.3762/bjoc.9.310

• ][17] and E3 [18] with full experimental details included for resolvins D3 [11], E2 [16] and E3 [18]. An improved synthesis of the C16–C20 fragment of resolvin E1 has also been reported [19]. We were interested in accessing amounts of RvD2 (1) for biological evaluation but without detailed synthetic

• sequence to follow and given the very high cost [20] of commercial 1 we elected to develop an alternative route to provide this important compound and analogues for further biological evaluation. Herein we describe a synthesis of RvD2 (1) which includes full experimental details so that other researchers

• RvD2 (1) has been completed using a common linchpin Wittig reaction. Using this approach, we were able to prepare sufficient quantities of this important inflammation resolving compound for further biological evaluation. Structures of resolvins D1 (1) and D2 (2). Retrosynthetic analysis of RvD2 (1

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

• Tobias A. M. Gulder,
• Snežana Neff,
• Traugott Schüz,
• Tammo Winkler,
• René Gees and
• Bettina Böhlendorf

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

• The myxobacterial strain Stigmatella aurantiaca MYX-030 was selected as promising source for the discovery of new biologically active natural products by our screening methodology. The isolation, structure elucidation and initial biological evaluation of the myxocoumarins derived from this strain are

Cyclopamine analogs bearing exocyclic methylenes are highly potent and acid-stable inhibitors of hedgehog signaling

• Johann Moschner,
• Anna Chentsova,
• Nicole Eilert,
• Irene Rovardi,
• Philipp Heretsch and
• Athanassios Giannis

Beilstein J. Org. Chem. 2013, 9, 2328–2335, doi:10.3762/bjoc.9.267

• 77030, USA 10.3762/bjoc.9.267 Abstract The chemical synthesis and biological evaluation of new cyclopamine analogs bearing exocyclic methylenes in different positions is described. Bis-exo-cyclopamine 6 was identified as a potent inhibitor of the Gli1-dependent luciferase expression in Shh-LIGHTII

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

• demonstrated allowing biological evaluation of either enantiomer and comparison of the obtained results. Through these studies it was found that the S-(−)-enantiomer of amlodipine is the biologically active one although there appears to be no significant difference in the pharmacokinetic behaviour between the

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

• trichlorocarbinol ester. A first biological evaluation showed that 204 displays antifungal activity. However, only 90 µg could be isolated and further biological screening was not possible [151]. Several sponge-derived macrolides have proven to be effective cytotoxic agents [152][153] and one could speculate that

Synthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes

• Tony Taldone,
• Anna Rodina,
• Erica M. DaGama Gomes,
• Matthew Riolo,
• Hardik J. Patel,
• Raul Alonso-Sabadell,
• Danuta Zatorska,
• Maulik R. Patel,
• Sarah Kishinevsky and
• Gabriela Chiosis

Beilstein J. Org. Chem. 2013, 9, 544–556, doi:10.3762/bjoc.9.60

• identification of two rotamers by NMR [22]. Biological evaluation of the biotinylated Hsp90 probes As indicated above, there are several requirements for a biotinylated probe to be useful in dissecting Hsp90 tumor biology in live cells. First, the probe should retain selective and tight binding to tumor Hsp90

• [M + H]+; HPLC: tR = 8.82. Biological evaluation of probes Hsp90 competition assay. For the competition studies, fluorescence polarization (FP) assays were performed as previously reported [9][23]. Briefly, FP measurements were performed on an Analyst GT instrument (Molecular Devices, Sunnyvale, CA

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

• Paweł Borowiecki,
• Małgorzata Milner-Krawczyk and
• Jan Plenkiewicz

Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56

De novo synthesis of D- and L-fucosamine containing disaccharides

• Daniele Leonori and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 332–341, doi:10.3762/bjoc.9.38

• availability of rare monosaccharides that cannot be isolated from natural sources is currently limiting the access to the synthesis and the biological evaluation of complex bacterial cell-surface glycans. Here, we report the synthesis of D- and L-fucosamine building blocks by a de novo approach from L- and D

Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide

• Lena Möller,
• Christian Hess,
• Jiří Paleček,
• Yi Su,
• Axel Haverich,
• Andreas Kirschning and
• Gerald Dräger

Beilstein J. Org. Chem. 2013, 9, 270–277, doi:10.3762/bjoc.9.33

• fluorescein R5N3 9 for analytic purposes. Supporting Information Details on the synthesis and analyses of building blocks and linkers, functionalization, biological evaluation and descriptions of analyses of TPX materials based on XPS, UV, IR and contact-angle measurements are found in Supporting Information

Development of peptidomimetic ligands of Pro-Leu-Gly-NH₂ as allosteric modulators of the dopamine D₂ receptor

• Swapna Bhagwanth,
• Ram K. Mishra and
• Rodney L. Johnson

Beilstein J. Org. Chem. 2013, 9, 204–214, doi:10.3762/bjoc.9.24

• same relative position in space [48][49]. Peptidomimetic negative modulators of the D2 dopamine receptor Biological evaluation of the C-8’a epimer of the type II β-turn PLG peptidomimetic 29a, spiro-bicyclic 29b, and of the C-8’a epimer of the polyproline II helix PLG peptidomimetic 49a, spiro-bicyclic

Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker

• Mayeul Collot,
• Steffen Eller,
• Markus Weishaupt and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 97–105, doi:10.3762/bjoc.9.13

• ], the need for synthetic tools has prompted synthetic carbohydrate chemists to develop methods for the accelerated synthesis of all types of glycans [9][10][11][12][13][14][15][16][17][18][19]. Automated synthesis of oligosaccharides is beginning to provide molecules for biological evaluation [20][21

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

• Laurie F. Mottram,
• Safiyyah Forbes,
• Brian D. Ackley and
• Blake R. Peterson

Beilstein J. Org. Chem. 2012, 8, 2156–2165, doi:10.3762/bjoc.8.243

• ). The ratio of fluorescence emission at λmax was used to calculate log D. Biological evaluation The N2 strain of C. elegans was cultured as described [47] and maintained at 20–22.5 °C. Fluorophores were added to normal growth media (NMG) liquid (at 45–55 °C), poured into Petri dishes (60 mm), and

Total synthesis and biological evaluation of fluorinated cryptophycins

• Christine Weiß,
• Tobias Bogner,
• Benedikt Sammet and
• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 2060–2066, doi:10.3762/bjoc.8.231

Automated synthesis of sialylated oligosaccharides

• Davide Esposito,
• Mattan Hurevich,
• Bastien Castagner,
• Cheng-Chung Wang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

• building blocks proved successful for the synthesis of representative Sia-containing oligosaccharides ready for biological evaluation. Results and Discussion Building-blocks preparation Many sialylation strategies utilize building blocks that require multistep syntheses [10]. In contrast, solid-phase

• way, the synthetic sialosides can be easily conjugated to probes for biological evaluation or labelled for instance with UV-active tags. Biotinylation is a typical example of a commonly employed labelling technique [30] and has been extensively used for instance as a functionalization technique for

• accessible starting materials. In combination with a fully automated synthesizer, the disaccharide building blocks have been exploited for the solid-phase synthesis of several oligosaccharides ready for biological evaluation. This work represents the first full account of an automated solid-phase synthesis

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

• Jin-Sheng Yu,
• Feng Zhou,
• Yun-Lin Liu and
• Jian Zhou

Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157

• -disubstituted oxindoles, using cheap and easily available starting materials and simple chiral catalysts to facilitate biological evaluation. We have developed the catalytic asymmetric addition of acrolein, allyltrimethylsilane or difluoroenoxysilanes to isatins to furnish differently substituted

An intramolecular inverse electron demand Diels–Alder approach to annulated α-carbolines

• Zhiyuan Ma,
• Feng Ni,
• Grace H. C. Woo,
• Sie-Mun Lo,
• Philip M. Roveto,
• Scott E. Schaus and
• John K. Snyder

Beilstein J. Org. Chem. 2012, 8, 829–840, doi:10.3762/bjoc.8.93

• library of eighty-eight α-carbolines was prepared by using this robust methodology for biological evaluation. Keywords: α-carboline; chemical diversity; inverse electron demand Diels–Alder; isatin; pyrido[2,3-b]indole; 1,2,4-triazine; Introduction In comparison with the well-known β-carbolines, α

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

• Davide Bini,
• Francesca Cardona,
• Matilde Forcella,
• Camilla Parmeggiani,
• Paolo Parenti,
• Francesco Nicotra and
• Laura Cipolla

Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58

• their preliminary biological evaluation as inhibitors against porcine and insect trehalase from C. riparius. Results and Discussion In previous studies by us and other research groups it was reported that 1-deoxynojirimycin (7) and its benzyl urea derivative 8 (Figure 2) [17][18] are trehalase

Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

• Matthias D’hooghe,
• Stéphanie Vandekerckhove,
• Karen Mollet,
• Karel Vervisch,
• Stijn Dekeukeleire,
• Liesbeth Lehoucq,
• Carmen Lategan,
• Peter J. Smith,
• Kelly Chibale and
• Norbert De Kimpe

Beilstein J. Org. Chem. 2011, 7, 1745–1752, doi:10.3762/bjoc.7.205

• parasite Plasmodium falciparum, too. Biological evaluation At first, compounds 6a–c, 8a–e, 9a–d, 12a,b, 14a–e, 15a–f and 16a–g were screened for in vitro antiplasmodial activity. All samples were tested in triplicate on one occasion against a chloroquine-sensitive (CQS) strain of P. falciparum (D10). Those

Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents

• María Jiménez,
• Wei Zhu,
• Andreas Vogt,
• Billy W. Day and
• Dennis P. Curran

Beilstein J. Org. Chem. 2011, 7, 1372–1378, doi:10.3762/bjoc.7.161

• ) (Figure 1). The later parts of this synthesis have been briefly communicated in a recent paper whose primary focus was biological evaluation [30]. Indeed, 3a and 3b prove to be promising anticancer agents with in vitro and cellular testing data superior to those of the 16-desmethyl analogs 2a and 2b, and

Synthesis of novel (1-alkanoyloxy- 4-alkanoylaminobutylidene)-1,1-bisphosphonic acid derivatives

• Petri A. Turhanen and
• Jouko J. Vepsäläinen

Beilstein J. Org. Chem. 2006, 2, No. 2, doi:10.1186/1860-5397-2-2

• proposed to be more lipophilic and are thus more soluble in organic solvents than alendronate and can be used as starting materials for the synthesis of new phosphorus end modified derivatives of HABBPA and which may represent as possible prodrugs of alendronate. Novel biological evaluation for selected