Org. and Biomol. Chem.

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Rhodium-Catalyzed ortho-Cyanation of Symmetrical Azobenzenes with N-Cyano-N-phenyl-p-toluenesulfonamide

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01736F, CommunicationJie Han, Changduo Pan, Xuefeng Jia, Chengjian Zhu
A rhodium-catalyzed ortho-cyanation of symmetrical azobenzenes is described employing N-cyano-N-phenyl-p-toluenesulfonamide as environmentally friendly cyanide source. The present protocol allows the synthesis of various benzonitirle derivatives in moderate to good yield...
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Synthesis of oligonucleotides containing N,N-disubstituted 3-deazacytosine nucleobases by post-elongation modification and their triplex-forming ability with double-stranded DNA

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01760A, PaperMasaaki Akabane-Nakata, Satoshi Obika, Yoshiyuki Hari
A phosphoramidite of a 2ʹ-O,4ʹ-C-methylene-bridged nucleoside, bearing 4-(2,4,6-triisopropylbenzenesulfonyloxy)pyridin-2-one as a nucleobase precursor, was synthesized and introduced into an oligonucleotide. Treatment with various secondary amines after elongating the oligonucleotide on an...
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The amphiphilic nature of saponins and their effects on artificial and biological membranes and potential consequences for red blood and cancer cells

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01652A, Review ArticleJoseph Helmuth Lorent, Joelle Leclercq, Marie-Paule Mingeot-Leclercq
Saponins, amphiphiles of natural origin with numerous biological activities, are widely used in the cosmetic and pharmaceutical industry. Some saponins exhibit relatively selective cytotoxic effects on cancer cells but the...
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Diversity-oriented synthesis of medicinally important 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives and higher analogs

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01446D, Review ArticleSambasivarao Kotha, Deepak Deodhar, Priti Khedkar
1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (Tic) is a constrained analog of phenylalanine (Phe). Tic unit has been identified as a core structural element present in several peptide-based drugs and forms an integral part...
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Decarboxylative Allylations of Ester Enolate Equivalents

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01752H, CommunicationJon Tunge, Yamuna Ariyarathna
A variety of ester enolate equivalents are generated in situ and undergo [small alpha]-allylation in high yields via palladium-catalyzed decarboxylative allylation. The transformations are complete within very short reaction times under...
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Frustrated Lewis Pair catalyzed Hydrosilylation and Hydrosilane mediated Hydrogenation of Fulvenes

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01346H, PaperSergej Tamke, Constantin Gabriel Daniliuc, Jan Paradies
The frustrated Lewis pair (FLP) mediated hydrosilylation of pentafulvenes is described yielding allyl silanes with high regioselectivity in excellent yields. While phenyl substituted allyl silanes undergo B(C6F5)3-mediated rearrangement to vinyl...
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Towards novel efficient and stable nuclear import signals: synthesis and properties of trimethylguanosine cap analogs modified within the 5',5'-triphosphate bridge

16 September, 2014 - 00:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01579G, PaperMalgorzata Zytek, Joanna Kowalska, Maciej Lukaszewicz, Blazej A Wojtczak, Joanna Zuberek, Aleksandra Ferenc-Mrozek, Edward Darzynkiewicz, Anna Niedzwiecka, Jacek Jemielity
A trimethylguanosine (TMG) cap is present at the 5' end of several small nuclear and nucleolar RNAs. Recently, it has been reported that the TMG cap is a potential nuclear...
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Synthesis and characterisation of glucosamine-NSAID bioconjugates

16 September, 2014 - 00:54

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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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.

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54
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

16 September, 2014 - 00:54

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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