Org. and Biomol. Chem.

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Preparation of indium nitronates and their Henry reactions

22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8593-8597
DOI: 10.1039/C4OB01468E, CommunicationRaquel G. Soengas, Rita Acurcio, Artur M. S. Silva
Indium nitronates were readily prepared from commercially available nitroalkanes by transmetallation of the corresponding lithium nitronates with indium salts. The Henry reaction of this nitronates with aldehydes afforded [small beta]-nitroalkanols in moderate to high yields and excellent stereoselectivity (when using chiral aldehydes).
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Anti-hepatitis B virus activities and absolute configurations of sesquiterpenoid glycosides from Phyllanthus emblica

22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8764-8774
DOI: 10.1039/C4OB01196A, PaperJun-Jiang Lv, Ya-Feng Wang, Jing-Min Zhang, Shan Yu, Dong Wang, Hong-Tao Zhu, Rong-Rong Cheng, Chong-Ren Yang, Min Xu, Ying-Jun Zhang
The sesquiterpenoid glycoside dimers isolated from Phyllanthus emblica have anti-HBV activities towards HBsAg and HBeAg secretions inhibition.
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A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8588-8592
DOI: 10.1039/C4OB01829J, CommunicationChandrasekhar Challa, Jamsheena Vellekkatt, Jaice Ravindran, Ravi S. 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.
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Cross-strand histidine-aromatic interactions enhance acyl-transfer rates in beta-hairpin peptide catalysts

22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8711-8718
DOI: 10.1039/C4OB01754D, PaperM. Matsumoto, S. J. Lee, M. R. Gagne, M. L. Waters
A His-aryl interaction in a beta-hairpin catalyst provides rate enhancements of up to 18 000 for acyl transfer catalysis.
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Highly enantioselective phosphination and hydrophosphonylation of azomethine imines: using chiral squaramide as a hydrogen bonding organocatalyst

22 October, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,8656-8670
DOI: 10.1039/C4OB01472C, PaperLing-Pei Kong, Nai-Kai Li, Shao-Yun Zhang, Xiang Chen, Min Zhao, Ya-Fei Zhang, Xing-Wang Wang
Highly enantioselective phosphination and hydrophosphonylation reactions of azomethine imines are respectively reported in this paper.
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Synthesis of PS/PO-Chimeric Oligonucleotides Using Mixed Oxathiaphospholane and Phosphoramidite Chemistry

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01837K, PaperJanina Baraniak, Ewa Radzikowska
Chimeric oligonucleotides containing phosphodiester and phosphorothioate linkages have been obtained using the solid phase synthesis. The oligonucleotide parts possessing natural internucleotide phosphate bonds were assembled using commercially available nucleoside 3'-O-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidites...
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Construction of Dispirocyclohexanes via Amine-Catalyzed [2 + 2 + 2] Annulations of Morita-Baylis-Hillman Acetates with Exocyclic Alkenes

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01927J, PaperRongshun Chen, Silong Xu, Xia Fan, Hanyuan Li, Yuhai Tang, Zhengjie He
Amine-catalyzed [2 + 2 + 2] annulations of one molecule of Morita-Baylis-Hillman (MBH) acetates 1 with two molecules of 2-(arylmethylidene)indane-1,3-diones 2 or methyleneindolinones 4 have been developed under very mild...
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Novel naphthoquinone derivatives and evaluation of trypanocidal and leishmanicidal activities

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01869A, PaperDenis Pires de Lima, Aline Alves dos Santos Naujorks, Adriano O da Silva, Rosangela S Lopes, Sergio de Albuquerque, Adilson Beatriz, Maria Rita Marques
Herein it is reported the synthesis of 12 new naphthoquinone derivatives, comprising 6 substituted 1,4-naphthoquinones and 6 heterocycle-fused naphthoquinones, as well as the evaluation of their trypanocidal and leishmanicidal activities....
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Synthesis of novel symmetrical 2-oxo-spiro[indole-3,4'-pyridines] by reaction of oxindoles with 1,2-diaza-1,3-dienes

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01959H, PaperFabio Mantellini, O A Attanasi, Lucia De Crescentini, Gianfranco Favi, Linda Antonella Campisi
A simple reaction of some oxindole derivatives with 1,2-diaza-1,3-dienes to produce 2-oxo-spiro[indole-3,4'-pyridines] in good yields is here described. This transformation represents a practical two steps approach to new and biologically...
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Biomineralization-inspired synthesis of functional organic/inorganic hybrid materials: organic molecular control of self-organization of hybrids

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01796J, Review ArticleAtushi Arakaki, Katsuhiko Shimizu, Mayumi Oda, Takeshi Sakamoto, Tatsuya Nishimura, Takashi Kato
Organisms produce various organic/inorganic hybrid materials, which are called biominerals. They form through the self-organization of organic molecules and inorganic elements under ambient conditions. Biominerals often show highly organized and...
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Synthesis and Biological Evaluation of (-)-Kainic Acid Analogues as Phospholipase D-Coupled Metabotropic Glutamate Receptor Ligands

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02002B, PaperChiara - Zanato, Sonia - Watson, Guy S. Bewick, Matteo Zanda, William T Harrison
(-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore...
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Improving catalyst activity in secondary amine catalysed transformations

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01916D, PaperJohn B Brazier, Julian Rowley, Timothy J K Gibbs, Sze Chak Yau, A R Kennedy, James A Platts, Leo Samulis, Nicholas C O Tomkinson
The effect on catalyst performance of altering substituents at the 2-position of the Macmillan imidazolidinone has been examined. Condensation of L-phenylalanine N-methyl amide with acetophenone derivatives results in a series...
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Bidirectional Macrocyclization of Peptides by Double Multicomponent Reaction

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01915F, PaperManuel G Ricardo, Fidel E Morales, Hilda Garay, Osvaldo Reyes, Dimitar Vasilev, Ludger A. Wessjohann, Daniel G. Rivera
Increasing the diversity of peptide cyclization methods is an effective way to access new types of macrocyclic chemotypes featuring a wide variety of ring sizes and topologies. Multicomponent reactions (MCRs)...
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Highly Enantioselective Reaction of 2-Oxindoles with (3-Indolyl)methanols by Cooperative Catalysis of Lewis Acid and Organocatalyst

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02035A, CommunicationChuan-Li ren, tao zhang, Xing-Yong Wang, Tao Wu, Jing Ma, Qing-Qing Xuan, Feng Wei, Hong-Yan Huang, Dong Wang, Li Liu
An efficient cooperative biscinchona alkaloid and Lewis acid catalytic system was developed in the enantioselective alpha-alkylation of 2-oxindoles with (3-indolyl)(phenyl)methanols to provide (2-oxindole)-linker-indole derivatives in good yields(70-83%) with high enantioselectivities(81-92%).
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Synthesis and biological evaluation of imidazo[1,5-a]pyridine-benzimidazole hybrids as inhibitors of both tubulin polymerization and PI3K/Akt pathway

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01930J, PaperAhmed Kamal, Subba Rao A.V., Lakshma Nayak V, Subba Reddy N. V., Swapna Konderu, Ramakrishna G, Mallika Alvala
A series of imidazo[1,5-a]pyridine-benzimidazole hybrids (5a-aa) were prepared and evaluated for their cytotoxic activity against a panel of sixty human tumor cell lines. Among them compounds 5d and 5l showed...
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New Insights in the Structure-Spectrum Relationship in S65T/H148D and E222Q/H148D Green Fluorescent Protein Mutants. A Theoretical Assessment.

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01462F, PaperPau Armengol, Ricard Gelabert, Miquel Moreno, Jose M Lluch
Green Fluorescent Protein (GFP) variant S65T/H148D recovers the A-band fluorescence lost in the single mutant S65T and it has been established that Asp148 is the alternate proton acceptor for the...
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Intramolcular Redox Reaction for the Synthesis of N-Aryl Pyrroles Catalyzed by Lewis Acids

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02009J, PaperHong-Jin Du, Le Zhen, Xiaoan Wen, Qing-Long Xu, Hongbin Sun
An efficient approach to N-aryl pyrroles via Lewis acid-mediated 1,5-hydride shift and isomerization of 2-(3-pyrroline-1-yl)arylaldehydes has been achieved in up to 89% yield. This methodology is applicable to the synthesis...
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Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01454E, PaperZhanhui Yang, Siqi Li, Zhong Zhang, Jiaxi Xu
The base-switched annuloselectivity, namely [2+2] and [2+2+2] selectivitiy, in the reactions of ethyl malonyl chloride and imines is successfully realized. In the presence of the weak nucleophilic base 2-chloropyridine, the...
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An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran by using alkoxybenzocyclobutenone as a reactive platform

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02012J, CommunicationToshiyuki Hamura, Kenta Asahina, Suguru Matsuoka, Ryosuke Nakayama
An efficient synthetic method of 1,3-bis(arylethynyl)isobenzofurans has been developed. Nucleophilic addition of alkynyllithium to benzocyclobutenone and subsequent oxidative ring cleavage of the four-membered ring gave keto-aldehyde, which, in turn, accepted...
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1-Trifluoromethylated isoquinolines via radical trifluoromethylation of isonitriles

20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02145B, PaperBo Zhang, Armido STUDER
A simple and efficient approach to biologically important 1-trifluoromethylated isoquinolines starting with readily prepared beta-aryl-alpha-isocyano-acrylates and commercially available Togni reagent as CF3 radical precursor is described. These transformations occur in...
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