Org. and Biomol. Chem.

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Stereodivergent Synthesis of the LFA-1 Antagonist BIRT 377 by Porcine Liver Esterase Desymmetrization and Curtius Rearrangement

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02303J, PaperThomas G Back, Aaron Johnson, Matthew J. Saunders
The LFA-1 inhibitor and leukocyte adhesion suppressor BIRT-377 was prepared in high enantiomeric excess by desymmetrization of dimethyl 2-p-bromobenzyl-2-methylmalonate, followed by condensation of the resulting carboxylic acid with 3,5-dichloroaniline, saponification...
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Synthesis, and QSAR analysis of anti-oncological active spiro-alkaloids

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02149E, PaperAS Girgis, Siva S Panda, I. S. Ahmed Farag, A. M. El-Shabiny, A. M. Moustafa, nasser saad ismail, Girinath G. Pillai, Chandramukhi S. Panda, Charles Dennis Hall, Alan R Katritzky
QSAR study describes the anti-neoplastic spiro-alkaloids with relevant molecular descriptors using CODESSA III software. The dispiro[3H-indole-3,2'-pyrrolidine-3',3''-piperidines] 24-48 were synthesized via [3+2]-cycloaddition reaction of azomethine ylides, (generated in situ via decarboxylative...
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Synthesis of N-Glycolyl Muramyl Dipeptide

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02147A, PaperShuo Xing, James L Gleason
A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy...
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Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis-Sonogashira coupling sequence

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02386B, PaperSidra Hassan, Anja Ullrich, Thomas J.J. Mueller
A novel chemoenzymatic three-component synthesis of (hetero)arylated propargyl amides in good yields based upon Novozyme[registered sign] 435 (Candida antarctica lipase B (CAL-B)) catalyzed aminolysis of methyl carboxylates followed by Sonogashira coupling...
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Sugar-Derived Amine Catalyzed Intramolecular Diels-Alder Reactions

3 December, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02219J, PaperTony K. M. SHING, Kwun W. Wu, Ho T Wu, Qicai Xiao
Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents [small alpha] to the amine can be introduced readily by a Grignard reaction, which...
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Probing coiled-coil assembly by paramagnetic NMR spectroscopy

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02125H, PaperTingTing Zheng, Aimee Boyle, Hana Robson Marsden, Dayenne Valdink, Giuliana Martelli, Jan Raap, Alexander Kros
Here a new method to determine the orientation of coiled-coil peptide motifs is described.
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Gold-catalyzed spiro-N,O-ketal synthesis

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02050B, PaperM. Grammatikopoulou, S. Thysiadis, V. Sarli
An efficient method for the synthesis of spiro-N,O-ketals with 5- and 6-membered rings was developed via a gold-catalyzed spiroamidoketalization of alkynyl amidoalcohols under mild conditions.
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Label-free fluorescence detection of kinase activity using a gold nanoparticle based indicator displacement assay

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02052A, PaperCristian Pezzato, Davide Zaramella, Massimiliano Martinelli, Gregory Pieters, Mario A. Pagano, Leonard J. Prins
A straightforward fluorescence indicator-displacement assay (IDA) has been developed for the quantitative analysis of ATP[rightward arrow]ADP conversion.
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Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02142H, PaperMayumi Yamaguchi, Akira Matsuda, Satoshi Ichikawa
Simplification of caprazamycins was conducted by scaffold-hopping of the structurally complex diazepanone moiety to the isoxazolidine scaffold.
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Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation

3 December, 2014 - 19:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02227K, PaperJiajia Guo, Shouyun Yu
An efficient and enantioselective strategy to synthesize benzoindolizidines via domino intramolecular aza-Michael addition/alkylation was developed.
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Preparation of Luminescent Chemosensors by Post-Functionalization of Vesicle Surfaces

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02327G, PaperBurkhard Koenig, Andreas Mueller
Surface-reactive luminescent vesicles were prepared by self-assembly of phospholipids, amphiphilic maleimides and fluorophors in aqueous solution. Those preformed liposomes were functionalized with various thiolated receptor units using a thiol-click reaction....
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Unprecedented one-pot sequential thiolate substitutions under mild conditions leading to a red emissive BODIPY dye 3,5,8-tris(PhS)-BODIPY

1 December, 2014 - 18:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01892C, CommunicationRobinson I. Roacho, Alejandro Metta-Magana, Eduardo Pena-Cabrera, Keith Pannell
Phenylthiol performs a thiol exchange with 8-MeS-BODIPY and activates/substitutes the 3,5 positions forming a tri-thiolated BODIPY.
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[gamma]-Cyclodextrin modulates the chemical reactivity by multiple complexation

1 December, 2014 - 18:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02113D, PaperJ. Fernandez-Rosas, M. Pessego, M. Cepeda-Plaza, N. Basilio, M. Parajo, P. Rodriguez-Dafonte, L. Garcia-Rio
Multiple recognition by cooperative/competitive mechanisms to form a 1 : 1 : 1 inclusion complex plays a crucial role in determining the chemical reactivity in the [gamma]-CD cavity.
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Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by combination of aromatic, hydrogen bond and electrostatic interactions

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02084G, PaperJorge Gonzalez, Sanja Tomic, Alberto Lopera, Lluis Guijarro, Ivo Piantanida, Enrique Garcia-Espana
Bis-polyaza pyridinophane scorpiands bind nucleotides in aqueous medium by 10-100 micromolar affinity, dominantly by electrostatic interactions between nucleotide phosphates and protonated aliphatic amines and assisted by aromatic stacking interactions. By...
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Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: An efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02286F, PaperAkhilesh K. Verma, Rakesh K Saunthwal, monika patel, abhinandan K. Danodia
An efficient palladium-catalyzed tandem approach for the synthesis of highly functionalized tetrahydroquinazolines 4a-q, and 5a-f by the reaction of o-haloanilines 1a-g with acrylates 2a-d and isothiocyanates 3aa-3ah/isocyanates 3ba-3bf via heck-conjoined...
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Tris(triazole) tripodal receptors as selective probes for citrate anion recognition and multichannel transition and heavy metal cations sensing

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02135E, PaperPedro Molina, Alberto Tarraga, Francisco Oton, Arturo Espinosa, Maria del Carmen Gonzalez
The three-armed pyrenyl-triazole receptor 1 behaves as highly selective fluorescent molecular sensor for citrate anion over similar carboxylates such as malate or tartrate. In addition, this receptor senses Cu2+ cations...
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Highly selective and sensitive detection of GSH using mesoporous silica nanoparticles capped with disulfide-containing oligo(ethylene glycol) chains

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02083A, CommunicationSameh Elsayed, Cristina Gimenez, Elena Aznar, Ramon Martinez-Manez, Felix Sancenon, Maurizio Licchelli
Mesoporous silica nanoparticles loaded with safranin O and capped with disulfide-containing oligo(ethylene glycol) chains were used for the selective and sensitive fluorimetric detection of GSH
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Synthesis and antimalarial evaluation of amide and urea derivatives based on the thiaplakortone A natural product scaffold

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01849D, PaperBrett Schwartz, Tina Skinner-Adams, Katherine T Andrews, Mark Coster, Michael Edstein, Donna MacKenzie, Susan Charman, Maria Koltun, Scott Blundell, Anna Campbell, Rebecca Pouwer, Ron Quinn, Karren Beattie, Peter C Healy, Rohan A Davis
A series of amide (8-32, 40-45) and urea (33, 34, 36-39) analogues based on the thiaplakortone A natural product scaffold were synthesised and screened for in vitro antimalarial activity against...
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Linear dialdehydes as promising substrates for aminocatalyzed transformations

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01805B, Review ArticleIndresh Kumar, Panduga Ramaraju, Nisar A. Mir, Anoop Singh
Organocatalytic domino reactions involving amine activation of carbonyl compounds have become the latest chemical technology towards the designing and development of useful synthetic methods. In this direction, linear dialdehydes such...
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Enzyme-triggered delivery of chlorambucil from conjugates based on the cell-penetrating peptide BP16

1 December, 2014 - 18:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01875C, PaperMarta Soler, Marta Gonzalez, Eduard Figueras, Xavi Ribas, Miquel Costas, Anna Massaguer, Marta Planas, Lidia Feliu
The undecapeptide KKLFKKILKKL-NH2 (BP16) is a non-toxic cell-penetrating peptide (CPP) that mainly internalizes cancer cells through a clathrin dependent endocytic mechanism and localizes in late endosomes. Moreover, this CPP is...
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