Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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(7S)-Kaitocephalin as a potent NMDA receptor selective ligand

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1206-1210
DOI: 10.1039/C5OB02301G, CommunicationYoko Yasuno, Makoto Hamada, Masanori Kawasaki, Keiko Shimamoto, Yasushi Shigeri, Toshifumi Akizawa, Motomi Konishi, Yasufumi Ohfune, Tetsuro Shinada
A structure-activity relationship (SAR) study of kaitocephalin, known to be a potent naturally occurring NMDA receptor ligand, was performed.
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The Ireland-Claisen rearrangement strategy towards the synthesis of the schizophrenia drug, (+)-asenapine

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1332-1337
DOI: 10.1039/C5OB02047F, PaperRaghunath Reddy Anugu, Prathama S. Mainkar, Balasubramanian Sridhar, Srivari Chandrasekhar
(+/-)-Asenapine, sold in the market as Saphris/Sycrest for the treatment of bipolar disorders, is synthesized in an optically pure form involving an Ireland-Claisen rearrangement as the key step. This approach allows access to all diastereomers.
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Borondifluoride complexes of hemicurcuminoids as bio-inspired push-pull dyes for bioimaging

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1311-1324
DOI: 10.1039/C5OB02295A, PaperEunsun Kim, Abdellah Felouat, Elena Zaborova, Jean-Charles Ribierre, Jeong Weon Wu, Sebastien Senatore, Cedric Matthews, Pierre-Francois Lenne, Carole Baffert, Artak Karapetyan, Michel Giorgi, Denis Jacquemin, Miguel Ponce-Vargas, Boris Le Guennic, Frederic Fages, Anthony D'Aleo
Synthesis, properties and biological imaging of hemicurcuminoid are presented.
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Green synthesis of dipyrromethanes in aqueous media catalyzed by SO3H-functionalized ionic liquid

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1302-1310
DOI: 10.1039/C5OB01953B, PaperW. Senapak, R. Saeeng, J. Jaratjaroonphong, T. Kasemsuk, U. Sirion
A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes from aldehydes and unsubstituted pyrrole catalyzed by SO3H-functionalized ionic liquids (SO3H-ILs) in aqueous media at room temperature.
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Solvent effect in [small beta]-phosphorylated nitroxides. Part 4: detection of traces of water by electron paramagnetic resonance

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1288-1292
DOI: 10.1039/C5OB02316E, PaperGerard Audran, Lionel Bosco, Paul Bremond, Teddy Butscher, Sylvain R. A. Marque
Detection by EPR of traces (0.1%) of water in polar solvent such as THF.
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In Vitro selectivity of an acyclic cucurbit[n]uril molecular container towards neuromuscular blocking agents relative to commonly used drugs

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1277-1287
DOI: 10.1039/C5OB02356D, PaperShweta Ganapati, Peter Y. Zavalij, Matthias Eikermann, Lyle Isaacs
We measure the binding affinity of Calabadion 2 toward 27 drugs to assess its selectivity toward rocuronium, vecuronium, and cisatracurium.
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Pd(0)-catalyzed domino C-N coupling/hydroamination/C-H arylation reactions: efficient synthesis and photophysical properties of azaindolo[1,2-f]phenanthridines

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1293-1301
DOI: 10.1039/C5OB02274F, PaperThang Ngoc Ngo, Frank Janert, Peter Ehlers, Do Huy Hoang, Tuan Thanh Dang, Alexander Villinger, Stefan Lochbrunner, Peter Langer
A series of new 7- and 4-azaindolo[1,2-f]phenanthridines were synthesized by a domino Pd(0)-catalyzed reaction, which involves three sequential steps: C-N coupling, hydroamination, and intramolecular C-H arylation.
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A practical method for the synthesis of peptoids containing both lysine-type and arginine-type monomers

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1211-1215
DOI: 10.1039/C5OB02279G, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.H. L. Bolt, S. L. Cobb
A practical synthetic procedure to synthesise linear and cyclic peptoids containing both arginine- and lysine-type residues within the same sequence has been developed. The methodology utilises orthogonal N-Boc and N-Dde protection, pyrazole-1-carboxamide as a guanidinylation reagent and is compatible with the sub-monomer method.
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Facile synthesis of aza-spirocyclopropanyl oxindoles by the reaction of 3-(2-bromoethyl)-indole with 2,3-dimethylimidazole-1-sulfonyl azide triflate

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1272-1276
DOI: 10.1039/C5OB02192H, PaperMei-Hua Shen, Ke Xu, Chu-Han Sun, Hua-Dong Xu
3-(2-Bromoethyl)indole reacts with 2,3-dimethylimidazole-1-sulfonyl azide triflate and then with an alcohol or amine to afford the corresponding aza-spirooxindole sulfonate and sulfonamide.
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N-Succinimidyl 3-((4-(4-[18F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([18F]SFBTMGMB): a residualizing label for 18F-labeling of internalizing biomolecules

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1261-1271
DOI: 10.1039/C5OB02258D, PaperGanesan Vaidyanathan, Darryl McDougald, Jaeyeon Choi, Marek Pruszynski, Eftychia Koumarianou, Zhengyuan Zhou, Michael R. Zalutsky
A nanobody 5F7 was labeled with 18F using [18F]RL-I, a residualizing label, with the preservation of affinity and immunoreactivity to HER2.
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Synthesis and bioactivity of antitubercular peptides and peptidomimetics: an update

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1177-1187
DOI: 10.1039/C5OB02298C, Review ArticleLuis M. De Leon Rodriguez, Harveen Kaur, Margaret A. Brimble
This mini-review provides an update on the synthesis and bioactivity of peptides and peptidomimetics that exhibit very potent antitubercular activity.
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The chemical synthesis of aryltetralin glycosides

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1188-1200
DOI: 10.1039/C5OB02188J, Review ArticleJian-Song Sun, Hui Liu, Xiao-Hong Guo, Jin-Xi Liao
A review placing its emphasis on the enantioselective synthesis of aryltetralin derivatives and the construction of key glycosydic linkages is presented.
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Divergent synthetic route to new cyclopenta[c]pyran iridoids: syntheses of jatamanin A, F, G and J, gastrolactone and nepetalactone

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1244-1251
DOI: 10.1039/C5OB02147B, PaperJaehoon Sim, Inah Yoon, Hwayoung Yun, Hongchan An, Young-Ger Suh
Six natural iridoids including jatamanin A, F, G and J, gastrolactone and nepetalactone have been synthesized via the efficient transformation of a core cyclopenta[c]pyran intermediate.
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Hg/Pt-catalyzed conversion of bromo alkynamines/alkynols to saturated and unsaturated [gamma]-butyrolactams/lactones via intramolecular electrophilic cyclization

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1252-1260
DOI: 10.1039/C5OB02125A, PaperYalla Kiran Kumar, Gadi Ranjith Kumar, Maddi Sridhar Reddy
An intramolecular electrophilic cyclization of bromo-alkynols/alkynamines is achieved for [gamma]-butyrolactams, [small alpha],[small beta]-unsaturated [gamma]-butyrolactones/lactams, [small alpha]-bromoketone and oxazinones under ambient conditions.
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Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill

26 January, 2016 - 00:17

Org. Biomol. Chem., 2016, 14,1201-1205
DOI: 10.1039/C5OB02061A, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Olga Eguaogie, Leonie A. Cooke, Patricia M. L. Martin, Francesco Ravalico, Louis P. Conway, David R. W. Hodgson, Christopher J. Law, Joseph S. Vyle
Exploiting the rapid kinetics and low solvent requirements of mechanochemically-activated reactions, the instability of phosphorothiolate monoesters was bypassed enabling one-pot hydrolytic desilylation and phosphate coupling to be achieved in a ball mill.
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A new generation of chiral phase-transfer catalysts

21 January, 2016 - 23:17

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C5OB02446C, Review ArticleShiho Kaneko, Yusuke Kumatabara, Seiji Shirakawa
A new generation of chiral phase-transfer catalysts is summarized.
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Structure-based design of 3-carboxy-substituted 1,2,3,4-tetrahydroquinolines as inhibitors of myeloid cell leukemia-1 (Mcl-1)

19 January, 2016 - 22:54

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C5OB02063H, CommunicationL. Chen, P. T. Wilder, B. Drennen, J. Tran, B. M. Roth, K. Chesko, P. Shapiro, S. Fletcher
A novel Mcl-1 inhibitor chemotype based on a tetrahydroquinoline carboxylic acid was developed utilizing structure-based design, which was subsequently validated by a fluorescence polarization competition assay and HSQC NMR analysis.
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A highly enantioselective Hg(II)-catalyzed Sakurai-Hosomi reaction of isatins with allyltrimethylsilanes

19 January, 2016 - 22:54

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C5OB02582F, CommunicationZhong-Yan Cao, Jia-Sheng Jiang, Jian Zhou
A chiral complex derived from (S)-difluorophos and Hg(OTf)2 is identified as a powerful catalyst for the Sakurai-Hosomi reaction of isatins with allyltrimethylsilane, allowing the facile synthesis of valuable building blocks 3-allyl-3-hydroxyoxindoles in up to 97% ee, with only 0.5-1.0 mol% of catalyst loading.
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A versatile synthesis of chiral [small beta]-aminophosphines

19 January, 2016 - 22:54

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C5OB02439K, PaperHsin Y. Su, Yixiong Song, Mark S. Taylor
A protocol for the synthesis of chiral [small beta]-aminophosphines by ring-opening of cyclic sulfamidates with metallated secondary phosphine oxides is described. It allows access to previously unknown derivatives having electron-deficient, electron-rich and sterically hindered P-aryl substituents.
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N-Bromosuccinimide promoted and base switchable one pot synthesis of [small alpha]-imido and [small alpha]-amino ketones from styrenes

19 January, 2016 - 22:54

Org. Biomol. Chem., 2016, 14,858-861
DOI: 10.1039/C5OB02034D, CommunicationMahesh H. Shinde, Umesh A. Kshirsagar
An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of [small alpha]-amino functionalized aryl ketones starting from commercially available styrenes has been developed.
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