Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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A lysosome-targeted drug delivery system based on sorbitol backbone towards efficient cancer therapy

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6564-6569
DOI: 10.1039/C4OB01153H, CommunicationSanthi Maniganda, Vandana Sankar, Jyothi B. Nair, K. G. Raghu, Kaustabh K. Maiti
A lysosome-targeted drug delivery system utilizing sorbitol scaffold linked to octa-guanidine and to a peptide substrate of lysosomal cysteine protease, cathepsin B.
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Metal-free oxidative olefination of primary amines with benzylic C-H bonds through direct deamination and C-H bond activation

14 August, 2014 - 16:54

Org. Biomol. Chem., 2014, 12,6557-6560
DOI: 10.1039/C4OB01025F, CommunicationLiang Gong, Li-Juan Xing, Tong Xu, Xue-Ping Zhu, Wen Zhou, Ning Kang, Bin Wang
An oxidative olefination reaction between aliphatic primary amines and benzylic sp3 C-H bonds has been achieved using N-bromosuccinimide as catalyst and tert-butyl hydroperoxide as oxidant.
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Modular Synthesis of Bis- and Tris-1,2,3-triazoles by Permutable Sequential Azide-Aryne and Azide-Alkyne Cycloadditions

12 August, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01654H, CommunicationSuguru Yoshida, Takako Nonaka, Takamoto Morita, Takamitsu Hosoya
A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient...
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Synthesis of Isoquinoline-1,3(2H,4H)-dione Derivatives via Cascade Reactions of N-Alkyl-N-methacryloyl Benzamide with Aryl Aldehydes

12 August, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01442A, CommunicationWannian Zhao, Ping Xie, Min Zhang, Ben Niu, Zhaogang Bian, Charles U. Pittman, Jr., Aihua Zhou
A cascade reaction between N-alkyl-N-methacryloylbenzamide and aryl aldehydes was developed to generate isoquinoline-1,3(2H,4H)-dione derivatives. The reaction involves oxidative cross coupling of the activated alkene from the N-alkyl-N-methacryloylbenzamide with the aldehyde...
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Asymmetric borylation of [small alpha],[small beta]-unsaturated esters catalyzed by novel ring expanded N-heterocyclic carbenes based on chiral 3,4-dihydro-quinazolinium compounds

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6554-6556
DOI: 10.1039/C4OB01101E, CommunicationLiliang Huang, Yong Cao, Manping Zhao, Zhongfeng Tang, Zhihua Sun
A series of novel ring expanded N-heterocyclic carbene (NHC) precursors were synthesized, which showed excellent enantioselectivities for borylation of [small alpha],[small beta]-unsaturated esters.
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Demonstration of a common indole-based aromatic core in natural and synthetic eumelanins by solid-state NMR

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6730-6736
DOI: 10.1039/C4OB01066C, PaperSubhasish Chatterjee, Rafael Prados-Rosales, Sindy Tan, Boris Itin, Arturo Casadevall, Ruth E. Stark
Comparing natural and synthetic eumelanin pigment structures: high-field 2D solid-state NMR reveals a common indole-based aromatic core for ubiquitous protective pigments that inspire engineered materials.
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N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6653-6660
DOI: 10.1039/C4OB01126K, PaperRui Zhu, Kai Yu, Zhenhua Gu
Allylic amides 3 were synthesized efficiently from homoallylic trichloroacetimidates 1via domino bromo-cyclization and elimination reactions.
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Novel phthalamides containing sulfiliminyl moieties and derivatives as potential ryanodine receptor modulators

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6643-6652
DOI: 10.1039/C4OB00716F, PaperSha Zhou, Tao Yan, Yuxin Li, Zhehui Jia, Baolei Wang, Yu Zhao, Yuanyuan Qiao, Lixia Xiong, Yongqiang Li, Zhengming Li
The present work firstly reported that the new diamides incorporating sulfiliminyl moieties are potential candidate structures for new ryanodine receptor modulators.
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Enhanced catalysis and enantioselective resolution of racemic naproxen methyl ester by lipase encapsulated within iron oxide nanoparticles coated with calix[8]arene valeric acid complexes

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6634-6642
DOI: 10.1039/C4OB01048E, PaperSerkan Sayin, Enise Akoz, Mustafa Yilmaz
In this study, two types of nanoparticles have been used as additives for the encapsulation of Candida rugosa lipase via the sol-gel method.
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An acridinium-based sensor as a fluorescent photoinduced electron transfer probe for proton detection modulated by anionic micelles

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6677-6683
DOI: 10.1039/C4OB00559G, PaperStefano Basili, Tiziana Del Giacco, Fausto Elisei, Raimondo Germani
Photoinduced electron transfer has been demonstrated to be the quenching mechanism for the fluorescent pH sensor based on the 9-amino-10-methylacridinium chromophore. The presence of anionic micelles causes a significant increase in the detection sensitivity of pH.
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SN2 regioselectivity in the esterification of 5- and 7-membered azacycloalkane quaternary salts: a DFT study to reveal the transition state ring conformation prevailing over the ground state ring strain

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6717-6724
DOI: 10.1039/C4OB00695J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Akihiro Kimura, Susumu Kawauchi, Takuya Yamamoto, Yasuyuki Tezuka
SN2 regioselectivity in 5- and 7-membered azacycloalkanes quaternary salts is directed by the transition state ring conformation.
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Synthesis and evaluation of antineurotoxicity properties of an amyloid-[small beta] peptide targeting ligand containing a triamino acid

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6684-6693
DOI: 10.1039/C4OB00959B, PaperDmytro Honcharenko, Partha Pratim Bose, Jyotirmoy Maity, Firoz Roshan Kurudenkandy, Alok Juneja, Erik Floistrup, Henrik Biverstal, Jan Johansson, Lennart Nilsson, Andre Fisahn, Roger Stromberg
A new triamino acid enables synthesis of an amyloid-[small beta] peptide (A[small beta]) targeting ligand with additional A[small beta]-ligand interactions that gives protection towards A[small beta]-induced reduction of gamma oscillations in hippocampal slice preparation.
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Azabicycles construction: the transannular ring contraction with N-protected nucleophiles

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6570-6579
DOI: 10.1039/C4OB01311E, Review ArticleAntonio Rizzo, Syuzanna R. Harutyunyan
Synthetic strategies are one of the most critical factors for the success of a synthetic campaign, but most importantly they are crucial for the economy and the efficiency of the sequence.
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Convenient access to readily soluble symmetrical dialkyl-substituted [small alpha]-oligofurans

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6661-6671
DOI: 10.1039/C4OB00898G, PaperEdward E. Korshin, Gregory M. Leitus, Michael Bendikov
A combination of heteroatom directed lithiation/CuCl2-induced homocoupling, Wittig olefination/Pd-catalyzed transfer hydrogenation followed by Suzuki-Miyaura or Stille cross-coupling enables convenient access to dialkyl-substituted [small alpha]-oligofurans of potential interest for organic electronics.
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Synthesis of methyl 2-cyano-3,12-dioxo-18[small beta]-olean-1,9(11)-dien-30-oate analogues to determine the active groups for inhibiting cell growth and inducing apoptosis in leukemia cells

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6706-6716
DOI: 10.1039/C4OB00703D, PaperXiaojing Li, Yuetong Wang, Yuan Gao, Lei Li, Xin Guo, Dan Liu, Yongkui Jing, Linxiang Zhao
A series of CDODO-Me-12 analogues were synthesized with improved ability to inhibit cell growth and induce apoptosis in HL-60 cells.
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Desilylative activation of TMSCN in chemoselective Strecker-Ugi type reaction: functional fused imidazoles as building blocks as an entry route to annulated purines

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6694-6705
DOI: 10.1039/C4OB00882K, PaperSankar K. Guchhait, Vikas Chaudhary
Nucleophilic activation of TMSCN as an isocyanide equivalent by DABCO-THF in the Strecker-Ugi reaction facilitates the synthesis of functional imidazoles which, as building blocks, afford access to C8-N9 annulated purines.
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Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6725-6729
DOI: 10.1039/C4OB00986J, PaperVikas S. Rawat, Thulasiram Bathini, S. Govardan, Bojja Sreedhar
Propargylamines are synthesized via metal-free activation of the C-halogen bond of dihalomethanes and the C-H bond of terminal alkynes in a three-component coupling without catalyst or additional base and under mild reaction conditions.
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Azide-alkyne cycloaddition for universal post-synthetic modifications of nucleic acids and effective synthesis of bioactive nucleic acid conjugates

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6624-6633
DOI: 10.1039/C4OB01132E, PaperYu-Chih Su, Yu-Lun Lo, Chi-Ching Hwang, Li-Fang Wang, Min Hui Wu, Eng-Chi Wang, Yun-Ming Wang, Tzu-Pin Wang
We have developed a universal approach for post-synthetic modifications of DNA/RNA by harnessing versatile phosphoramidation and powerful azide-alkyne cycloaddition reactions.
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Copper catalyzed C-O bond formation via oxidative cross-coupling reaction of aldehydes and ethers

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6549-6553
DOI: 10.1039/C4OB00862F, CommunicationQuan Wang, Hao Zheng, Wen Chai, Dianyu Chen, Xiaojun Zeng, Renzhong Fu, Rongxin Yuan
A practical and efficient construction of C-O bonds via oxidative cross-coupling reaction of aldehydes and ethers has been realized under open air. When 2 mol% copper was used as the catalyst, various [small alpha]-acyloxy ethers were obtained with up to 93% isolated yield.
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Synthesis, photophysical and cytotoxicity evaluations of DNA targeting agents based on 3-amino-1,8-naphthalimide derived Troger's bases

12 August, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,6610-6623
DOI: 10.1039/C3OB42213E, PaperSamantha Murphy, Sandra A. Bright, Fergus E. Poynton, Thomas McCabe, Jonathan A. Kitchen, Emma B. Veale, D. Clive Williams, Thorfinnur Gunnlaugsson
The synthesis, spectroscopic and biological evaluation of five fluorescent Troger's bases is described. These were shown to bind to DNA, being rapidly taken up into cancer cells and induce apoptosis after 4-24 hours.
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