Royal Society of Chemistry

Synthesis and characterisation of glucosamine-NSAID bioconjugates

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01681E, PaperRachel A. Jones, Yann Thillier, Siva S. Panda, Nicole Rivera Rosario, C. Dennis Hall, Alan R. Katritzky
Synthetic strategies to prepare non-steroidal anti-inflammatory drug-glucosamine bioconjugates.
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Antibacterial epipolythiodioxopiperazine and unprecedented sesquiterpene from Pseudallescheria boydii, a beetle (Coleoptera)-associated fungus

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01494D, PaperRen Xiang Tan, Qi Wu, Nan Jiang, wen bo han, Hui Ming Ge, Zhi Kai Guo, Ng Seik Weng, Yaning Mei
Pseudallescheria boydii residing in the gut of coleopteran (Holotrichia parallela) larve produces four new epipolythiodioxopiperazines (ETPs) boydines A-D (3-6) and two novel sesquiterpene boydenes A (7) and B (10), in...
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Enantioselective Synthesis of 3-Substituted 1,2-Oxazinanes Via Organocatalytic Intramolecular Aza-Michael Addition

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01646G, CommunicationShuanghua Cheng, Shouyun Yu
A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions...
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Preparation of indium nitronates and their Henry reactions

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01468E, CommunicationRaquel G. Soengas, Rita Acurcio, Artur Silva
Indium nitronates were readily prepared from commercially available nitroalkanes by transmetalation of the corresponding lithium nitronates with indium salts. Henry reaction of this indium organometallics with aldehydes afforded [small beta]-nitroalkanols in...
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Anti Hepatitis B Virus Activities and Absolute Configurations of Sesquiterpenoid Glycosides from Phyllanthus emblica

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01196A, PaperLv Jun-Jiang, Ya-Feng Wang, Jing-Min Zhang, Shan Yu, Hong-Tao Zhu, Dong Wang, Rong-Rong Cheng, Chong-Ren Yang, Min Xu, Ying-Jun Zhang
During the process exploring anti-viral compounds from Phyllanthus species, eight new highly oxygenated bisabolane sesquiterpenoid glycosides phyllaemblicins G1-G8 (1-8) were isolated from Phyllanthus emblica, along with three known compounds, phyllaemblicin...
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Highly Diastereoselective 1,3-Dipolar Cycloadditions of Chiral Non-Racemic Nitrones to 1,2-Diaza-1,3-dienes: An Experimental and Computational Investigation

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01371A, PaperPedro Merino, Roberta Majer, Olga Konechnaya, Ignacio Delso, Tomas Tejero, O A Attanasi, Stefania Santeusanio
Asymmetric 1,3-dipolar cycloadditions between 1,2-diaza-1,3-dienes and chiral non-racemic nitrones to give 3-substituted-5-diazenyl isoxazolidines have been studied both experimentally and theoretically. Whereas cyclic nitrones provide complete selectivity for the cycloaddition reaction...
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Effect of C7-Substitution of 1-Arylsulfonyl-5-(N-hydroxyacrylamide)indolines on the Selectivity Toward Subclass of Histone Deacetlyase.

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00542B, PaperHsueh-Yun Lee, Li-Ting Wang, Yu-Hsuan Li, Shiow-Lin Pan, Yi-Lin Chen, Che-Ming Teng, Jing-Ping Liou
This study focused on the substitution effect at C7 position of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indolines. Compound 9, (E)-3-(7-amino-1-(4-methoxyphenylsulfonyl)indolin-5-yl)-N-hydroxyacrylamide, displayed 4- to 14-fold more potent antiproliferative activity than SAHA (1). Notably, 9 possessed specific...
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N- and C-functionalisation of seven-membered iminosugars with long alkyl chains generate potent glycosidase inhibitors and F508del-CFTR correctors

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00325J, PaperYves Bleriot, Martine Mondon, Nathalie Fontelle, virginie cendret, jerome desire, George W J Fleet, Terry D Butters, Dominic S Alonzi, gabriele twigg, Shinpei Nakagawa Nakagawa, y hirokami, Isao Adachi, Frederic Becq, Caroline Norez, johanna bertrand, Jerome Marrot, Atsushi Kato, ren iwachi
The glycosidase inhibitory properties of synthetic C-alkyl and N-alkyl six-membered iminosugars have been extensively studied leading to therapeutic candidates. The related seven-membered iminocyclitols have been less examined despite the report...
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Clicked bis-PEG-Peptide Conjugates for Studying Calmodulin-Kv7.2 Channel Binding

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01338G, PaperAngeles Bonache, Alessandro Alaimo, Covadonga Malo, Oscar Millet, Alvaro Villarroel, Rosario Gonzalez-Muniz
The recombinant Kv7.2 calmodulin (CaM) binding site (Q2AB CaMBD) shows a high tendency to aggregate, thus complicating biochemical and structural studies. To facilitate these studies we have conceived bis-PEG-peptide CaMBD-mimetics...
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A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01829J, Communicationchandrasekhar challa, Jamsheena Vellekkatt, Jaice Ravindran, Ravi Shankar Lankalapalli
A metal-free one-pot cascade annulation of acyclic substrates dienaminodioate, cinnamaldehydes and allyl amine was achieved for the synthesis of polyfunctional biaryl-2-carbaldehydes. The reaction proceeds at room temperature by a trifluoroacetic...
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NIS-Mediated Oxidative Cyclization of N-(2-Trifluoromethyl-3-alkynyl) hydroxylamines: A Facile Access to 4- Trifluoromethyl-5-acylisoxazoles

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01790K, PaperLi Zhang, Qin Zeng, Ao Mao, Ziang Wu, Tian Luo, Yuanjing Xiao, Junliang Zhang
A novel NIS-mediated oxidative cyclization of N-(2-trifluoromethyl-3-alkynyl)hydroxylamines was developed, which provides a facile access to 4-trifluoromethyl -5-acylisoxazoles in 39-91% yields. Various types of commonly used electrophilic halogen source such as...
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Cross-strand histidine-aromatic interactions enhance acyl-transfer rates in beta-hairpin peptide catalysts

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01754D, PaperMasaomi Matsumoto, Stephen Lee, Michel Gagne, Marcey Waters
A reactive tagging methodology was used to select the species most reactive to an acylation reagent from a solid phase library of beta hairpin peptides. Hits bearing an electron-rich aromatic...
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Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: an easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00922C, PaperSudipta Kumar Manna, Gautam Panda
Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized in high yields from easily accessible (S)-amino acid-derived chiral carbocations.
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Peptidomimetic Inhibitors of N-Myristoyltransferase from Human Malaria and Leishmaniasis Parasites

Org. and Biomol. Chem. - 5 hours 40 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01669F, CommunicationTayo O Olaleye, James A Brannigan, Shirley M Roberts, Anthony J Wilkinson, Robin J Leatherbarrow, Edward William Tate
N-Myristoyltransferase (NMT) has been shown to be essential in Leishmania and subsequently validated as a drug target in Plasmodium. Herein, we discuss the use of antifungal NMT inhibitors as a...
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Performance of DFT methods and origin of stereoselectivity in bipyridine N,N[prime or minute]-dioxide catalyzed allylation and propargylation reactions

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01719F, PaperDiana Sepulveda, Tongxiang Lu, Steven E. Wheeler
It is shown that many DFT methods correctly predict the stereoselectivity of bipyridine N,N[prime or minute]-dioxide catalyzed alkylation reactions despite predicting the incorrect low-lying transition state structures. A novel explanation of the origin of stereoselectivity in these reactions is also provided.
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Multi-channel colorimetric and fluorescent probes for differentiating between cysteine and glutathione/homocysteine

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01219D, PaperLun Song, Ti Jia, Wenjia Lu, Nengqin Jia, Weibing Zhang, Junhong Qian
Three fluorescent probes were rationally designed to discriminate between Cys and GSH/Hcy. Cys and GSH can be differentiated by the naked eye.
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Asymmetric synthesis of (3S,1[prime or minute]S)-3-(1-amino-2,2,2-trifluoroethyl)-1-(alkyl)-indolin-2-one derivatives by addition of (S)-N-t-butylsulfinyl-3,3,3-trifluoroacetaldimine to 1-(alkyl)-indolin-2-ones

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01453G, CommunicationPing Qian, Chen Xie, Lingmin Wu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han, Yi Pan
This paper for the first time presents the addition reactions between amide-derived nucleophiles and CF3-containing N-sulfinyl-imines, with synthetically useful diastereoselectivity and chemical yields.
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Oxidative damage of aromatic dipeptides by the environmental oxidants NO2[radical dot] and O3

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01577K, PaperL. F. Gamon, J. M. White, U. Wille
Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in aromatic N- and C-protected dipeptides upon exposure to the environmental pollutants NO2[radical dot] and O3.
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ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions: synthesis of dihydropyran-fused diterpenoids

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01040J, PaperChunyong Ding, Lili Wang, Haijun Chen, Christopher Wild, Na Ye, Ye Ding, Tianzhi Wang, Mark A. White, Qiang Shen, Jia Zhou
A mild and concise approach for the construction of a 3,4-dihydro-2H-pyran ring integrated into the A-ring of the natural product oridonin is reported herein.
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Anion effects to deliver enhanced iridium catalysts for hydrogen isotope exchange processes

Org. and Biomol. Chem. - 5 hours 40 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01570C, CommunicationAlan R. Kennedy, William J. Kerr, Rory Moir, Marc Reid
Enhanced catalyst efficiency and solvent applicability has been achieved for hydrogen isotope exchange processes with Ir(I) complexes possessing larger, more weakly coordinating counterions.
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