Org. and Biomol. Chem.

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A unified lead-oriented synthesis of over fifty molecular scaffolds

25 November, 2014 - 17:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02287D, PaperRichard G. Doveston, Paolo Tosatti, Mark Dow, Daniel J. Foley, Ho Yin Li, Amanda J. Campbell, David House, Ian Churcher, Stephen P. Marsden, Adam Nelson
Sourcing large numbers of lead-like compounds is a major challenge; a unified synthetic approach enabled the efficient synthesis of 52 diverse lead-like molecular scaffolds from just 13 precursors.
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Water-Soluble Aryl-Extended Calix[4]pyrroles with Unperturbed Aromatic Cavities: Synthesis and Binding Studies

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02108H, PaperPablo Ballester, Stanislaw Zankowski, Daniel Hernandez-Alonso, Louis Adriaenssens
We report the synthesis of a novel, water-soluble aryl-extended calix[4]pyrrole receptor. The water-solubilising groups are placed at the lower rim of the receptor, leaving the binding pocket unperturbed and open...
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UV-visible and 1H-15N NMR Spectroscopic Studies of Colorimetric Thiosemicarbazide Anion Sensors

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02091J, PaperKristina N Farrugia, Damjan Makuc, Agnieszka Podborska, Konrad Szacilowski, Janez Plavec, David C Magri
Four model thiosemicarbazide anion chemosensors containing three N-H bonds, substituted with phenyl and/or 4-nitrophenyl units, were synthesised and studied for their anion binding abilities with hydroxide, fluoride, acetate, hypophosphate and...
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A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: design, synthesis, and biological evaluation

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01605J, PaperGaofei Wei, Shuai Wang, Weijing Luan, Shanshan Cui, Fengran Li, Yongliang Liu, Yang Liu, Mao-sheng Cheng
A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds...
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Gd(OTf)3-Catalyzed the Synthesis of Geranyl Esters for the Intramolecular Radical Cyclization of their Epoxides Mediated by Titanocene(III)

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02312A, PaperWilliam Hernan Garcia, Carlos Eduardo Puerto Galvis, Vladimir V. Kouznetsov
A selective and mild method for the esterification of a variety of carboxylic acids with geraniol was developed. We demonstrated that the use of triphenylphosphine, I2, 2-methyl imidazole or imidazole...
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Accelerated Fmoc Solid-phase Synthesis of Peptides with Aggregation-disrupting Backbones

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02260B, PaperYi-Chao Huang, chaojian guan, Xiang-Long Tan, chenchen chen, Qingxiang Guo, Yiming Li
In this work, we describe an accelerated solid-phase synthetic protocol of ordinary or difficult peptides involving air-bath heating and amide protection. For the Hmsb-based backbone amide protection, an optimized acyl...
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Metal-Catalyzed Formation of 1,3-Cyclohexadienes: A Catalyst-Dependent Reaction

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01922A, PaperShifa Zhu, Xiaobing Huang, Tian-Qi Zhao, Tongmei Ma, Huanfeng Jiang
A metal-dependent and complementary catalytic method to synthesize the cyclohexadienes has been developed. When gold or indium salts were used as catalysts, 1,3-cyclohexadiene (1,3-CHD) could be obtained; when Cu(OTf)2 was...
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Probing coiled-coil assembly by paramagnetic NMR spectroscopy

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02125H, PaperTingting zheng, Aimee Boyle, Hana Robson Marsden, Dayenne Valdink, Giuliana Martelli, jan raap, alexander kros
Here a new method to determine the oligomeric state and orientation of coiled-coil peptide motifs is described. Peptides K and E, which are designed to form a parallel heterodimeric complex...
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Multi-substituted 8-Aminoimidazo[1,2-a]pyrazines by Groebke-Blackburn-Bienayme Reaction and Their Hsp90 Inhibitory Activity

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01865F, PaperRen Jing, Yang Min, Liu Hongchun, Cao Danyan, Chen Danqi, Li Jian, Tang Le, He Jianhua, Yue-Lei Chen, Meiyu Geng, Bing Xiong, Jingkang Shen
Using 2,3-diamino pyrazine substrate and yttrium triflate catalyst, various 2-alkyl and aryl substituted 3,8-diaminoimidazo[1,2-a]pyrazines could be efficiently prepared through Groebke-Blackburn-Bienayme MCR. In particular, a novel 2-piperonyl 3,8-diaminoimidazo[1,2-a]pyrazine structure could be...
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Rhodium-catalysed arylative annulation of 1,4-enynes with arylboronic acids

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02210F, CommunicationTakanori Matsuda, Shoichi Watanuki
The rhodium(I)-catalysed arylative annulation of 1,4-enynes with arylboronic acids was investigated. The reaction was found to proceed via an addition-1,4-rhodium migration-addition sequence, affording the corresponding 1,1-disubstituted 3-(arylmethylene)indanes.
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Gold-Catalyzed Spiro-N,O-Ketal Synthesis

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02050B, PaperVasiliki Sarli, Margarita Grammatikopoulou, Savvas Thysiadis
An efficient method for the synthesis of spiro-N,O-ketals with 5- and 6-membered rings was developed via a gold-catalyzed spiroamidoketalization of alkynyl amidoalcohols under mild conditions. This methodology has been successfully...
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Preparation of polydopamine nanocapsules in miscible tetrahydrofuran/buffer mixture

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02080D, CommunicationYunzhou Ni, Wenfeng Jiang, Gangsheng Tong, Jianxin Chen, Jie Wang, Huimei Li, Chunyang Yu, Xiaohua Huang, Yongfeng Zhou
A miscible tetrahydrofuran/ tris buffer mixture has been used to fabricate polydopamine hollow capsules with a size of 200 nm and with a shell thickness of 40 nm. An unusual...
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Ruthenium-Catalyzed Direct C3 Alkylation of Indoles with [small alpha],[small beta]-Unsaturated Ketones

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02124J, PaperLin Dong, Shuai-Shuai Li, Hui Lin, Xiao-Mei Zhang
In this paper, a simple and highly efficient ruthenium-catalyzed direct C3 alkylation of indoles with various [small alpha],[small beta]-unsaturated ketones via C-H activation has been developed. This novel methodology exhibits broad substrate...
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Palladium-Catalyzed Oxidative Cross-Coupling of Azole-4-carboxylates with Indoles: An approach to the Synthesis of Pimprinine

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01844C, PaperHequan Yao, Haipin Zhou, Kuo Gai, Jinyi Xu, Xiaoming Wu, Aijun Lin
An efficient and straightforward method for the construction of 5-(3-indolyl)-azoles incorporating the privileged structures indoles and azoles via palladium-catalyzed double C-H bond cleavage under mild conditions was disclosed. As expected,...
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Label-free fluorescence detection of kinase activity using a gold nanoparticle based indicator displacement assay

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02052A, PaperCristian Pezzato, Davide Zaramella, Massimiliano Martinelli, Gregory Pieters, Mario A Pagano, Leonard Jan Prins
A straightforward indicator-displacement assay (IDA) has been developed for the quantitative analysis of ATP[rightward arrow]ADP conversion. The IDA relies on the use of gold nanoparticles passivated with a monolayer of thiols...
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Synthesis and Biological Evaluation of Novel Pyrano[3,2-c]carbazole Derivatives as Anti-tumor Agents inducing apoptosis via tubulin polymerization inhibition

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02015D, Paperadisherla indrasena, pannala padmaja reddy, garikapati koteswara rao rao, basireddy subba reddy, nibedita patil, Anver Basha Shaik, narayana reddy, Dubey P.K, manika pal bhadra
A series of novel pyrano[3,2-c]carbazole derivatives have been synthesized in a simple one-pot, three component reaction of aromatic aldehydes, malononitrile/ethylcyanoacetate and 4-hydroxycarbazoles catalyzed by triethylamine. The antiproliferative activity of the...
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Tunneling in Tocopherol-Mediated Peroxidation of 7-Dehydrocholesterol

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02377C, PaperHubert Muchalski, Libin Xu, N A Porter
The peroxidation of 7-dehydrocholesterol (7-DHC), a biosynthetic precursor to vitamin D3 and cholesterol, has been linked to the pathophysiology of Smith-Lemli-Optiz syndrome (SLOS), a devastating human disorder. In SLOS, 7-DHC...
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Synthesis of 3,3-dichloroindolin-2-ones from Isatin-3-hydrazones and (Dichloroiodo)benzene

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02213K, CommunicationGraham Murphy, Keith E Coffey, Ryan Moreira, Farhana Z Abbas
Aryl- and N-substituted isatins were converted to isa-tin-3-hydrazones and subjected to a dichlorination re-action with PhICl2. Lewis base-catalysis was key to the reaction occurring rapidly and chemoselectively, providing 3,3-dichloroindolin-2-ones in...
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Synthesis of Isoxazolidine-containing Uridine Derivatives as Caprazamycin Analogues

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02142H, PaperMayumi Yamaguchi, Akira Matsuda, Satoshi Ichikawa
Simplification of caprazamycins, which are promising antibacterial nucleoside natural products, was conducted by scaffold-hopping of the structurally complex diazepanone moiety to the isoxazolidine scaffold. The designed isoxazolidine-containing uridine derivatives were...
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Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/ alkylation

25 November, 2014 - 17:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02227K, PaperJiajia Guo, Shouyun Yu
An efficient and enantioselective strategy to synthesize benzoindolizidines from [small alpha], [small beta]-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were enabled by cinchona alkaloid-derived quaternary ammonium salts...
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