Org. and Biomol. Chem.

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Non-isoprenoid polyene natural products - structures and synthetic strategies

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7877-7899
DOI: 10.1039/C4OB01337A, Review ArticleKatrina S. Madden, Fathia A. Mosa, Andrew Whiting
This review provides insight into the variety of structures and biological activities found in the non-isoprenoid family of polyene natural products and examines the strategies and synthetic methods applied for the polyenic components in particular by way of examples.
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Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,8072-8078
DOI: 10.1039/C4OB01358A, PaperXuan Zhao, Tian-Ze Li, Jing-Ying Qian, Feng Sha, Xin-Yan Wu
The first enantioselective aza-Morita-Baylis-Hillman reaction of acrylates with ketimines was achieved in excellent yields and good enantioselectivities.
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Conformationally constrained nucleoside phosphonic acids - potent inhibitors of human mitochondrial and cytosolic 5[prime or minute](3[prime or minute])-nucleotidases

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7971-7982
DOI: 10.1039/C4OB01332H, PaperOndrej Simak, Petr Pachl, Milan Fabry, Milos Budesinsky, Tomas Jandusik, Ales Hnizda, Radka Sklenickova, Magdalena Petrova, Vaclav Veverka, Pavlina Rezacova, Jiri Brynda, Ivan Rosenberg
Conformationally constrained nucleoside phosphonic acids - potent inhibitors of human mitochondrial and cytosolic 5[prime or minute](3[prime or minute])-deoxynucleotidases.
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Asymmetric Michael addition of ketones to nitroolefins: pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,8008-8018
DOI: 10.1039/C4OB01223B, PaperAhmed Kamal, Manda Sathish, Vunnam Srinivasulu, Jadala Chetna, Kunta Chandra Shekar, Shalini Nekkanti, Yellaiah Tangella, Nagula Shankaraiah
New pyrrolidinyl-oxazole-carboxamides were synthesized and utilized as efficient organocatalysts for asymmetric Michael addition reaction. In addition, computational mechanistic studies were performed.
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Multiple optical properties of a naphthoquinone pigment: 2-methyl-3-(hydroxyphenylthio)-1,4-naphthalenedione

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7965-7970
DOI: 10.1039/C4OB01058B, PaperHirotaka Akiyama, Takafumi Inoue, Nobuo Tajima, Reiko Kuroda, Yoshitane Imai
Naphthoquinone pigments 2-methyl-3-(4- or 2-hydroxyphenylthio)-1,4-naphthalenedione show characteristic multiple optical properties in solution and in the solid state.
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Pyrazole-oxadiazole conjugates: synthesis, antiproliferative activity and inhibition of tubulin polymerization

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7993-8007
DOI: 10.1039/C4OB01152J, PaperAhmed Kamal, Anver Basha Shaik, Sowjanya Polepalli, Vangala Santosh Reddy, G. Bharath Kumar, Soma Gupta, K. V. S. Rama Krishna, Ananthamurthy Nagabhushana, Rakesh K. Mishra, Nishant Jain
A library of pyrazole-oxadiazole conjugates were synthesized and investigated for their antiproliferative activity in human cancer cell lines.
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Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7923-7926
DOI: 10.1039/C4OB01440E, CommunicationLiang Wang, Wenting Wu, Qun Chen, Mingyang He
Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group.
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Discovery and SAR study of piperidine-based derivatives as novel influenza virus inhibitors

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,8048-8060
DOI: 10.1039/C4OB01079E, PaperGuoxin Wang, Longjian Chen, Tongmei Xian, Yujie Liang, Xintao Zhang, Zhen Yang, Ming Luo
A series of 4-(quinolin-4-yloxy)piperidine-1-carboxylate derivatives were identified as novel and potent inhibitors of the influenza virus through structural modification of a compound from a high-throughput screen.
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An experimental and theoretical study of reaction mechanisms between nitriles and hydroxylamine

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,8036-8047
DOI: 10.1039/C4OB00854E, PaperAttila Voros, Zoltan Mucsi, Zoltan Baan, Geza Timari, Istvan Hermecz, Peter Mizsey, Zoltan Finta
The industrially relevant reaction between nitriles and hydroxylamine yielding amidoximes was studied in different molecular solvents and in ionic liquids.
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Structurally modified natural sesquiterpene lactones constitute effective and less toxic schistosomicidal compounds

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7957-7964
DOI: 10.1039/C4OB00426D, PaperDaiane Cristina Sass, Gustavo Oliveira Morais, Ricardo Augusto Crema Miranda, Lizandra Guidi Magalhaes, Wilson Roberto Cunha, Raquel Alves dos Santos, Nilton Syogo Arakawa, Fernando Batista Da Costa, Mauricio Gomes Constantino, Vladimir Constantino Gomes Heleno
Selective obtention of novel natural sesquiterpene lactone derivatives with interesting schistosomicidal activity and low toxicity, together with complete NMR assignments.
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Conversion of S-phenylsulfonylcysteine residues to mixed disulfides at pH 4.0: utility in protein thiol blocking and in protein-S-nitrosothiol detection

30 September, 2014 - 03:17

Org. Biomol. Chem., 2014, 12,7942-7956
DOI: 10.1039/C4OB00995A, PaperB. D. Reeves, N. Joshi, G. C. Campanello, J. K. Hilmer, L. Chetia, J. A. Vance, J. N. Reinschmidt, C. G. Miller, D. P. Giedroc, E. A. Dratz, D. J. Singel, P. A. Grieco
A protocol denoted as the thiosulfonate switch featuring sequential protein thiol blocking and conversion of protein-S-nitrosothiols to mixed disulfides bearing a fluorescent probe at pH 4.0 is reported.
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Surface patterning with natural and synthetic polymers via an inverse electron demand Diels-Alder reaction employing microcontact chemistry

28 September, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,7828-7835
DOI: 10.1039/C4OB01379D, PaperOliver Roling, Artur Mardyukov, Sebastian Lamping, Benjamin Vonhoren, Stefan Rinnen, Heinrich F. Arlinghaus, Armido Studer, Bart Jan Ravoo
Bioorthogonal ligation methods are the focus of current research due to their versatile applications in biotechnology and materials science for post-functionalization and immobilization of biomolecules.
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Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification

28 September, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,7659-7672
DOI: 10.1039/C4OB00835A, Review ArticleJames J. Sahn, Brett A. Granger, Stephen F. Martin
Multicomponent assembly processes are key steps in the synthesis of diverse polycyclic heterocycles with a broad array of biological activities.
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Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

28 September, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,7786-7791
DOI: 10.1039/C4OB01611D, PaperKah-Yee Li, Jianbing Jiang, Martin D. Witte, Wouter W. Kallemeijn, Wilma E. Donker-Koopman, Rolf G. Boot, Johannes M. F. G. Aerts, Jeroen D. C. Codee, Gijsbert A. van der Marel, Herman S. Overkleeft
Of six cyclophellitol analogues, the N-pentylaziridine is the most effective retaining human beta-glucosidase inhibitor considering potency and compound stability.
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Theoretical insight into the antioxidant properties of melatonin and derivatives

26 September, 2014 - 02:17

Org. Biomol. Chem., 2014, 12,7820-7827
DOI: 10.1039/C4OB01396D, PaperJeffrey R. Johns, James A. Platts
Density functional theory calculations on melatonin, metabolites and synthetic derivatives thereof, and a range of other biological antioxidant molecules are presented, with a view to understanding the antioxidant ability of these molecules.
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The first synthesis of the antiangiogenic homoisoflavanone, cremastranone

26 September, 2014 - 02:17

Org. Biomol. Chem., 2014, 12,7673-7677
DOI: 10.1039/C4OB01604A, CommunicationBit Lee, Halesha D. Basavarajappa, Rania S. Sulaiman, Xiang Fei, Seung-Yong Seo, Timothy W. Corson
The homoisoflavanone cremastranone is synthesized for the first time and shown to block human retinal endothelial cell angiogenesis in vitro.
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Iron-catalyzed direct difunctionalization of alkenes with dioxygen and sulfinic acids: a highly efficient and green approach to [small beta]-ketosulfones

26 September, 2014 - 02:17

Org. Biomol. Chem., 2014, 12,7678-7681
DOI: 10.1039/C4OB01369G, CommunicationWei Wei, Jiangwei Wen, Daoshan Yang, Min Wu, Jinmao You, Hua Wang
A novel and efficient iron-catalyzed direct difunctionalization of alkenes with sulfinic acids and dioxygen for the synthesis of [small beta]-ketosulfones has been developed.
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Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C

26 September, 2014 - 02:17

Org. Biomol. Chem., 2014, 12,7682-7685
DOI: 10.1039/C4OB01436G, CommunicationR. Matovic, F. Bihelovic, M. Gruden-Pavlovic, R. N. Saicic
The desmethyl analogue of abyssomicin C was synthesized. The synthetic analogue retained its antibacterial activity, whereas its cytotoxicity decreased for three orders of magnitude, as compared to the natural product.
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Synthesis and evaluation of a photoresponsive quencher for fluorescent hybridization probes

26 September, 2014 - 02:17

Org. Biomol. Chem., 2014, 12,7844-7858
DOI: 10.1039/C4OB01185F, PaperMarina Kovaliov, Chaim Wachtel, Eylon Yavin, Bilha Fischer
dUDAB modified probes are promising probes for gene quantification in real-time PCR detection and as photoswitchable devices.
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Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O2[prime or minute]-alkylated RNA monomers

26 September, 2014 - 02:17

Org. Biomol. Chem., 2014, 12,7758-7773
DOI: 10.1039/C4OB01183J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Saswata Karmakar, Andreas S. Madsen, Dale C. Guenther, Bradley C. Gibbons, Patrick J. Hrdlicka
Energetically activated double-stranded probes with interstrand arrangements of intercalator-functionalized nucleotides enable recognition of mixed-sequence DNA with single nucleotide fidelity.
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