Org. and Biomol. Chem.

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Synthesis and biological evaluation of dual action cyclo-RGD/SMAC mimetic conjugates targeting [small alpha]v[small beta]3/[small alpha]v[small beta]5 integrins and IAP proteins

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3288-3302
DOI: 10.1039/C4OB00207E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.M. Mingozzi, L. Manzoni, D. Arosio, A. Dal Corso, M. Manzotti, F. Innamorati, L. Pignataro, D. Lecis, D. Delia, P. Seneci, C. Gennari
Dual action cyclo-RGD/SMAC mimetic conjugates endowed with in vitro activity against anti-apoptotic IAPs and pro-angiogenetic integrins are reported.
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Effective catalysis of imine metathesis by means of fast transiminations between aromatic-aromatic or aromatic-aliphatic amines

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3282-3287
DOI: 10.1039/C4OB00107A, PaperMaria Ciaccia, Silvia Pilati, Roberta Cacciapaglia, Luigi Mandolini, Stefano Di Stefano
Transiminations involving aromatic or aliphatic amines were found to be fast enough to be effectively employed in the catalysis of imine metathesis.
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Nucleophilic addition to N-alkoxyamides

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3147-3150
DOI: 10.1039/C4OB00389F, PerspectiveTakaaki Sato, Noritaka Chida
Amide-selective nucleophilic addition using N-alkoxyamides minimized extra protecting group manipulations and redox reactions, resulting in the concise total synthesis of gephyrotoxin.
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Inverse solvent effects in the heterogeneous and homogeneous epoxidation of cis-2-heptene with [2-percarboxyethyl]-functionalized silica and meta-chloroperbenzoic acid

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3246-3250
DOI: 10.1039/C4OB00253A, PaperRossella Mello, Jeymy T. Sarmiento-Monsalve, Diana Vargas-Oviedo, Rafael Acerete, Maria Elena Gonzalez-Nunez, Gregorio Asensio
The organized solvent layer on the solid surface determines the reaction rate in the heterogeneous epoxidation of cis-2-heptene.
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Cooperative hydrolysis of aryl esters on functionalized membrane surfaces and in micellar solutions

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3175-3180
DOI: 10.1039/C4OB00247D, PaperM. Poznik, B. Konig
Catalytic hydrolysis of peptides, proteins, phosphates or carboxylate esters in nature is catalysed by enzymes, which are efficient, fast and selective.
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Convergent routes to substituted naphthylamides

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3251-3264
DOI: 10.1039/C4OB00339J, PaperNgoc Diem My Tran, Samir Z. Zard
Substituted 1- and 2-naphthylamides can be obtained by the radical addition-cyclisation of amido-containing phenacyl xanthates to vinyl pivalate followed by acid catalysed aromatisation.
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Synthesis of new anionic carbosilane dendrimers via thiol-ene chemistry and their antiviral behaviour

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3222-3237
DOI: 10.1039/C4OB00162A, PaperMarta Galan, Javier Sanchez Rodriguez, Jose Luis Jimenez, Miguel Relloso, Marek Maly, F. Javier de la Mata, M. A. Munoz-Fernandez, Rafael Gomez
Thiol-ene chemistry, enable the identification of anionic carbosilane dendrimers as readily available, good and safe candidates for vaginal microbicides against HIV.
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Synthesis and evaluation of monophosphoryl lipid A derivatives as fully synthetic self-adjuvanting glycoconjugate cancer vaccine carriers

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3238-3245
DOI: 10.1039/C4OB00390J, PaperZhifang Zhou, Mohabul Mondal, Guochao Liao, Zhongwu Guo
Monophosphoryl lipid A derivatives were used as both carrier molecules and built-in adjuvants to create fully synthetic self-adjuvanting glycoconjugate cancer vaccines.
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"Click and go": simple and fast folic acid conjugation

1 May, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,3181-3190
DOI: 10.1039/C4OB00150H, PaperAlexandre F. Trindade, Raquel F. M. Frade, Ermelinda M. S. Macoas, Catia Graca, Catarina A. B. Rodrigues, Jose M. G. Martinho, Carlos A. M. Afonso
A novel approach for conjugation of folic acid is presented allowing for its quantitative conjugation with several types of molecules (fluorescent probes) and materials (polymers and silica) based on strain-promoted alkyne-azide cycloaddition, without the need for expensive chromatographic purifcation.
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Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3191-3200
DOI: 10.1039/C4OB00126E, PaperDandan Liu, Long Ai, Fan Li, Annan Zhao, Jingbo Chen, Hongbin Zhang, Jianping Liu
Anhydrocaranine, [gamma]-lycorane and putative amarbellisine were synthesized based on a series reactions including a novel cyclopropyl ring-opening rearrangement.
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N,N[prime or minute]-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea: a privileged motif for catalyst development

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3151-3162
DOI: 10.1039/C4OB00306C, Review ArticleZhiguo Zhang, Zongbi Bao, Huabin Xing
This review summarizes the key developments of N,N[prime or minute]-bis[3,5-bis(trifluoromethyl)phenyl]thiourea (Schreiner's thiourea)-mediated reactions with the aim to further expand the applications of (thio)urea-based catalysts.
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The development of catalytic nucleophilic substitution reactions: challenges, progress and future directions

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,2993-3003
DOI: 10.1039/C4OB00032C, Review ArticleJie An, Ross M. Denton, Tristan H. Lambert, Eric D. Nacsa
Bimolecular nucleophilic substitution reactions of alcohols are fundamentally important transformations in organic chemistry yet, to date, they are relatively underdeveloped with respect to catalysis.
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Cooperative N-heterocyclic carbene (NHC)-Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3009-3015
DOI: 10.1039/C4OB00145A, CommunicationYu Zhang, Yingyan Lu, Weifang Tang, Tao Lu, Ding Du
A novel synthesis of spirooxindoles has been developed by cooperative NHC-Lewis acid-mediated formal [3 + 2] annulations of alkynyl aldehydes with isatins.
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Synthesis and identification of proposed biosynthetic intermediates of saxitoxin in the cyanobacterium Anabaena circinalis (TA04) and the dinoflagellate Alexandrium tamarense (Axat-2)

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3016-3020
DOI: 10.1039/C4OB00071D, CommunicationShigeki Tsuchiya, Yuko Cho, Keiichi Konoki, Kazuo Nagasawa, Yasukatsu Oshima, Mari Yotsu-Yamashita
We synthesized the genetically predicted biosynthetic intermediates of saxitoxin (STX) (1), 2, 6 and 7, and identified 2 and 6 in microorganisms.
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Highly enantioselective Michael addition of diethyl malonate to chalcones catalyzed by cinchona alkaloids-derivatived bifunctional tertiary amine-thioureas bearing multiple hydrogen-bonding donors

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3163-3166
DOI: 10.1039/C4OB00203B, CommunicationYulong Liu, Xie Wang, Xiaoyun Wang, Wei He
Both enantiomers of diethyl 2-(3-oxo-1,3-arylpropyl)malonate are easily prepared by a highly enantioselective Michael addition of diethyl malonate with chalcones catalyzed by cinchona alkaloids-derivatived organocatalysts.
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Tetrathiafulvalene mono- and bis-1,2,3-triazole precursors by click chemistry: structural diversity and reactivity

29 April, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,3167-3174
DOI: 10.1039/C4OB00148F, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Thomas Biet, Narcis Avarvari
The ruthenium-catalyzed alkyne-azide cycloaddition reaction allowed the synthesis of electroactive TTF-mono and -bis(1,2,3-triazoles) which were structurally characterized and investigated in protonation and alkylation reactions.
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A selenium-contained aggregation-induced "turn-on" fluorescent probe for hydrogen peroxide

27 April, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,3004-3008
DOI: 10.1039/C4OB00206G, CommunicationYe-Xin Liao, Kun Li, Ming-Yu Wu, Tong Wu, Xiao-Qi Yu
A novel selenium-contained aggregation-induced "turn-on" fluorescent probe was presented, which could selectively respond to hydrogen peroxide over other ROS in aqueous solution.
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Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles

27 April, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,3026-3036
DOI: 10.1039/C4OB00115J, PaperOleg V. Larionov, David Stephens, Adelphe M. Mfuh, Hadi D. Arman, Anastasia S. Naumova, Gabriel Chavez, Behije Skenderi
Mechanistic and synthetic studies of the Mo/P-catalyzed N-oxidation of N-heterocycles with hydrogen peroxide shed light on the role and nature of the catalytically active species.
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Catalytic amounts of triarylaminium salt initiated aerobic oxidative coupling of N-aryl tetrahydroisoquinolines

27 April, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,3123-3128
DOI: 10.1039/C3OB42454E, PaperCongde Huo, Cheng Wang, Mingxia Wu, Xiaodong Jia, Xicun Wang, Yong Yuan, Haisheng Xie
A novel, efficient in catalytic amounts, stable radical cation triarylaminium salt induced aerobic oxidative [small alpha]-C-H functionalization of tertiary amines has been developed.
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N-heterocyclic carbene (NHC)-modulated Pd/Cu cocatalyzed three-component synthesis of 2,6-diarylquinolines

27 April, 2014 - 13:54

Org. Biomol. Chem., 2014, 12,3114-3122
DOI: 10.1039/C4OB00231H, PaperChen Xu, Hong-Mei Li, Xiao-Er Yuan, Zhi-Qiang Xiao, Zhi-Qiang Wang, Wei-Jun Fu, Bao-Ming Ji, Xin-Qi Hao, Mao-Ping Song
An efficient NHC-modulated Pd/Cu cocatalyzed three-component coupling reaction for the synthesis of 2,6-diarylquinolines via oxidation, cyclization and Suzuki reactions.
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