Org. and Biomol. Chem.
RSC - Org. Biomol. Chem. latest articles
Updated: 1 day 8 hours ago
Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells
DOI: 10.1039/C3OB00011G, PaperAna S. Leal, Rui Wang, Jorge A. R. Salvador, Yongkui Jing
A series of new oleanolic acid derivatives with an imidazole ring in several positions of the oleanane backbone were synthesised, fully characterized and evaluated for their antiproliferative activity in AsPC-1 cells. Compound 27 was further tested in other cell lines.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
First diastereoselective [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides
DOI: 10.1039/C3OB26766K, PaperCarlos Arroniz, Juan Molina, Sonia Abas, Elies Molins, Josep M. Campanera, F. Javier Luque, Carmen Escolano
The first silver-catalysed [3 + 2] cycloaddition reaction of diethyl isocyanomethylphosphonate and N-substituted maleimides furnished bicyclic [small alpha]-iminophosphonates with complete diastereoselectivity.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Recent applications of arene diazonium salts in organic synthesis
DOI: 10.1039/C3OB27366K, PerspectiveFanyang Mo, Guangbin Dong, Yan Zhang, Jianbo Wang
Recent advances involving arene diazonium salts as starting materials or active intermediates for various synthetically useful applications are summarized.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Design and synthesis of stable [small alpha]-diazo-[small beta]-oxo sulfoxides
DOI: 10.1039/C3OB27061K, PaperStuart G. Collins, Orlagh C. M. O'Sullivan, Patrick G. Kelleher, Anita R. Maguire
Diazo transfer adjacent to a sulfoxide moiety to provide stable, isolable [small alpha]-diazo-[small beta]-oxo sulfoxides has been achieved. Use of monocyclic and bicyclic sulfoxide precursors is critical in enabling isolation of stable derivatives, through introduction of conformational constraint, while acyclic [small alpha]-diazo-[small beta]-oxo sulfoxides are too labile to isolate.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Overriding the alkynophilicity of gold: catalytic pathways from higher energy Au(I)-substrate complexes and reactant deactivation via unproductive complexation in the gold(I)-catalyzed propargyl Claisen rearrangement
DOI: 10.1039/C2OB27231H, PaperDinesh V. Vidhani, John W. Cran, Marie E. Krafft, Igor V. Alabugin
The competition between catalytically important mechanistic pathways in the Au-promoted propargyl Claisen rearrangement depends on a variety of electronic effects unrelated to Au-alkyne coordination.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes
DOI: 10.1039/C3OB26915A, PaperD. J. C. Prasad, G. Sekar
A new copper-catalyzed in situ generation of aryl thiolates strategy was developed for the one-pot synthesis of substituted benzothiazoles from 2-iodoanilides using xanthate as thiol precursor. This one-pot protocol was successfully utilized for the synthesis of a potent antitumor agent PMX 610 and substituted benzothiophenes.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Cationic lipophosphoramidates with two disulfide motifs: synthesis, behaviour in reductive media and gene transfection activity
DOI: 10.1039/C3OB27261C, PaperAurore Fraix, Tony Le Gall, Mathieu Berchel, Caroline Denis, Pierre Lehn, Tristan Montier, Paul-Alain Jaffres
The synthesis of cationic lipids with two disulfide motifs in the hydrophobic domain is reported. They compact pDNA and release it rapidly in the presence of DTT as a reductive agent.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Chromenoquinoline-based thiol probes: a study on the quencher position for controlling fluorescent Off-On characteristics
DOI: 10.1039/C2OB27192C, PaperDnyaneshwar Kand, Arunasree Marasanapalli Kalle, Pinaki Talukdar
A comparative study on chromenoquinoline-based fluorescent thiol probes is reported which features a higher Off-On response for hindered thiol exhibited by the probe with maleimide at the groove position of the fluorophore.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Orthogonal synthesis of a heterodimeric ligand for the development of the GdIII-GaIII ditopic complex as a potential pH-sensitive MRI/PET probe
DOI: 10.1039/C2OB27200H, PaperNikolay Vologdin, Gabriele A. Rolla, Mauro Botta, Lorenzo Tei
A heterodimeric DO3A-sulfonamide-AAZTA ligand and its GdIII-GaIII heteroditopic complex were synthesised via an orthogonal route aiming to build a platform for the preparation of an efficient smart MRI/PET probe sensitive to pH.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
An efficient Au-catalyzed synthesis of isomukonidine, clausine L, mukonidine, glycosinine, mukonal, and clausine V from propadienyl methyl ether
DOI: 10.1039/C2OB27432A, PaperYouai Qiu, Dengke Ma, Chunling Fu, Shengming Ma
Naturally occurring carbazole alkaloids such as isomukonidine, clausine-L, mukonidine, glycosinine, mukonal, and clausine V were synthesized through a gold-catalyzed cyclization reaction of 1-(indol-2-yl)-2-methoxy-2,3-allenols.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Synthesis of helically twisted [1 + 1]macrocycles assisted by amidinium-carboxylate salt bridges and control of their chiroptical properties
DOI: 10.1039/C2OB27054D, PaperYuji Nakatani, Yoshio Furusho, Eiji Yashima
Novel twisted [1 + 1]macrocycles were prepared through amidinium-carboxylate salt bridges, whose chirality could be controlled by acid-base interactions and zinc coordination.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Synthesis and biological studies of neopetrosiamides as inhibitors of cancer cell invasion
DOI: 10.1039/C3OB27238A, PaperKaitlyn M. Towle, Jennifer L. Chaytor, Hongqiang Liu, Pamela Austin, Michel Roberge, Calvin D. Roskelley, John C. Vederas
The tricyclic peptides neopetrosiamides A and B, isolated from the marine sponge Neopetrosia sp., are potential antimetastatic agents that inhibit tumour cell invasion by both amoeboid and mesenchymal migration pathways.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process
DOI: 10.1039/C3OB27493D, CommunicationJumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat, Tanita Gettongsong
Rearrangement of arylmethyl azides under acidic conditions and subsequent reaction with 3-ethoxyacrylate in the domino fashion provide a convenient access to a variety of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Investigation on the 1,6-naphthyridine motif: discovery and SAR study of 1H-imidazo[4,5-h][1,6]naphthyridin-2(3H)-one-based c-Met kinase inhibitors
DOI: 10.1039/C2OB26710A, PaperYong Wang, Zhong-Liang Xu, Jing Ai, Xia Peng, Jian-Ping Lin, Yin-Chun Ji, Mei-Yu Geng, Ya-Qiu Long
A new class of c-Met inhibitors were designed and discovered based on the 1,6-naphthyridine scaffold by constraining the 7,8-positions into a urea functionality.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Benzofuran and indole synthesis via Cu(I)-catalyzed coupling of N-tosylhydrazone and o-hydroxy or o-amino phenylacetylene
DOI: 10.1039/C2OB26867A, PaperTiebo Xiao, Xichang Dong, Lei Zhou
A general and practical method to synthesize 2-substituted benzofurans and indoles is described. This method employs easily accessible N-tosylhydrazones and o-hydroxy or o-amino phenylacetylenes as substrates. The reaction proceeds through a CuBr-catalyzed coupling-allenylation-cyclization sequence.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Asymmetric rearrangement of racemic epoxides catalyzed by chiral Bronsted acids
DOI: 10.1039/C3OB27285K, CommunicationMinyang Zhuang, Haifeng Du
An asymmetric 1,2-rearrangement of racemic epoxides via a hydrogen-shift process was realized to furnish chiral alcohols with up to 50% ee.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
A sterically demanding organo-superbase avoids decomposition of a naked trifluoromethyl carbanion directly generated from fluoroform
DOI: 10.1039/C3OB27368G, CommunicationHiroyuki Kawai, Zhe Yuan, Etsuko Tokunaga, Norio Shibata
The direct non-metallic trifluoromethylation of carbonyl compounds using fluoroform in the presence of t-Bu-P4 afforded trifluoromethyl alcohols in high yields.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles
DOI: 10.1039/C3OB27407A, CommunicationYuta Nagase, Hiroyuki Shirai, Masayoshi Kaneko, Eiji Shirakawa, Teruhisa Tsuchimoto
Treating 3-(hetero)arylindoles with propargyl ethers under indium catalysis gave (hetero)aryl[c]carbazoles, which were found to be more efficient emitters compared to the corresponding [a]-analogs.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Metal-free syn-dioxygenation of alkenes
DOI: 10.1039/C3OB27387C, PerspectiveMichael J. Rawling, Nicholas C. O. Tomkinson
This review highlights the methods available for the metal-free syn-dioxygenation of alkenes.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry
Phosphine-containing Lewis base catalyzed cyclization of benzofuranone type electron-deficient alkenes with allenoates: a facile synthesis of spirocyclic benzofuranones
DOI: 10.1039/C3OB27288E, CommunicationXin Li, Feng Wang, Nan Dong, Jin-Pei Cheng
A regioselective [3 + 2] cycloaddition of benzofuranone type active olefins with allenoates catalyzed by trivalent phosphines has been developed.
The content of this RSS Feed (c) The Royal Society of Chemistry
Categories: Royal Society of Chemistry