Org. and Biomol. Chem.

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Pd-catalyzed carbonylation for the construction of tertiary and quaternary carbon centers with sp3 carbon partners

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5243-5249
DOI: 10.1039/C4OB00568F, PaperWei Lu, Yang Li, Chao Wang, Dong Xue, Jian-Gang Chen, Jianliang Xiao
The first examples of a Pd-catalyzed carbonylation of aryl boronic acids with sp3 carbon partners are presented.
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Multivalent agents containing 1-substituted 2,3,4-trihydroxyphenyl moieties as novel synthetic polyphenols directed against HIV-1

29 June, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,5278-5294
DOI: 10.1039/C4OB00445K, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Aida Flores, Maria Jose Camarasa, Maria Jesus Perez-Perez, Ana San-Felix, Jan Balzarini, Ernesto Quesada
A series of synthetic polyphenols inspired by the multivalent architecture of naturally-occurring hydrolysable tannins exhibited selective inhibitory activity against HIV-1.
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Unusual truncation of N-acylated peptoids under acidic conditions

29 June, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,5222-5226
DOI: 10.1039/C3OB42572J, PaperSoomin Kim, Goutam Biswas, Shinae Park, Arim Kim, Hyunjung Park, Eunsook Park, Jeongmi Kim, Yong-Uk Kwon
Systematic studies on the unusual truncation of N-acylated peptoids were carried out to examine the electronic effects of acyl groups, and thus to control the formation of deletion sequences based on a plausible mechanism.
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A unifying mechanism for the rearrangement of vinyl allene oxide geometric isomers to cyclopentenones

27 June, 2014 - 03:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00562G, PaperAdan B. Gonzalez-Perez, Alexander Grechkin, Angel R. de Lera
Z-Vinyl allene oxides are predicted to rearrange with high fidelity to stereodefined cyclopentenones through intermediate cyclopropanones.
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Fluoroacetate biosynthesis from the marine-derived bacterium Streptomyces xinghaiensis NRRL B-24674

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4828-4831
DOI: 10.1039/C4OB00970C, CommunicationSheng Huang, Long Ma, Ming Him Tong, Yi Yu, David O'Hagan, Hai Deng
Streptomyces xinghaiensis is the first fluorometabolite producing microorganism identified from the marine environment.
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Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4924-4931
DOI: 10.1039/C4OB00801D, PaperNicholas G. White, Ana R. Colaco, Igor Marques, Vitor Felix, Paul D. Beer
A [2]rotaxane incorporating the novel 3-amido-phenyl-triazolium motif exhibits unusually high selectivity for halide anions over larger more basic oxoanions. Computational studies offer insight into this selectivity preference.
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[2]Pseudorotaxane formation between rigid Y-shaped 2,4,5-triphenylimidazolium axles and [24]crown-8 ether wheels

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4824-4827
DOI: 10.1039/C4OB00975D, CommunicationNasim Farahani, Kelong Zhu, Nadim Noujeim, Stephen J. Loeb
A new templating motif for the formation of [2]pseudorotaxanes is described in which rigid, Y-shaped axles with an imidazolium core and aromatic substituents at the 2-, 4- and 5-positions interact with [24]crown-8 ether wheels ([24]crown-8 and dibenzo[24]crown-8).
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Dual responsive supramolecular amphiphiles: guest molecules dictate the architecture of pyridinium-tailored anthracene assemblies

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4820-4823
DOI: 10.1039/C4OB00936C, CommunicationJun Hu, Peiyi Wang, Yuan Lin, Song Yang, Baoan Song, Qian Wang
By introducing an electron-deficient guest molecule and a counter anion, the assembly morphology of 1-[11-(2-anthracenylmethoxy)-11-oxoundecyl]pyridinium bromide (2-AP) was transformed to microsheets and nanofibers from microtubes, respectively.
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Synthesis of DIBAC analogues with excellent SPAAC rate constants

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,5031-5037
DOI: 10.1039/C4OB00694A, PaperMarjoke F. Debets, Jasper S. Prins, Donny Merkx, Sander S. van Berkel, Floris L. van Delft, Jan C. M. van Hest, Floris P. J. T. Rutjes
Four new DIBAC analogues showed excellent SPAAC rate constants making them comparable to the fastest cyclooctynes currently known.
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Rare Streptomyces sp. polyketides as modulators of K-Ras localisation

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4872-4878
DOI: 10.1039/C4OB00745J, PaperAngela A. Salim, Xue Xiao, Kwang-Jin Cho, Andrew M. Piggott, Ernest Lacey, John F. Hancock, Robert J. Capon
A rare class of oxanthromicin polyketides was isolated from a soil-derived Streptomyces sp. SAR-investigation showed that selected analogues can induce significant K-Ras plasma membrane mislocalisation and can synergise the K-Ras plasma membrane mislocalisation properties of staurosporine.
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A total synthesis of (+)-negamycin through isoxazolidine allylation

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4879-4884
DOI: 10.1039/C4OB00537F, PaperRoderick W. Bates, Rab'iah Nisha Khanizeman, Hajime Hirao, Yu Shan Tay, Patcharaporn Sae-Lao
The [small beta]-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate.
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Cerium(III)-catalyzed cascade cyclization: an efficient approach to functionalized pyrrolo[1,2-a]quinolines

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4837-4840
DOI: 10.1039/C4OB00708E, CommunicationChengtao Feng, Yizhe Yan, Zhenglei Zhang, Kun Xu, Zhiyong Wang
A general and practical route to the synthesis of multisubstituted pyrrolo[1,2-a]quinolines has been described from 2-alkylazaarenes and nitroolefins using cerium chloride as a catalyst via a tandem Michael addition, cyclization and aromatization.
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Design and synthesis of lipid-coupled inositol 1,2,3,4,5,6-hexakisphosphate derivatives exhibiting high-affinity binding for the HIV-1 MA domain

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,5006-5022
DOI: 10.1039/C4OB00350K, PaperHiroshi Tateishi, Kensaku Anraku, Ryoko Koga, Yoshinari Okamoto, Mikako Fujita, Masami Otsuka
Lipid-coupled inositol 1,2,3,4,5,6-hexakisphosphate binds to HIV-1 MA tightly through both electrostatic and hydrophobic interactions.
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Antitumour indolequinones: synthesis and activity against human pancreatic cancer cells

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4848-4861
DOI: 10.1039/C4OB00711E, PaperMartyn Inman, Andrea Visconti, Chao Yan, David Siegel, David Ross, Christopher J. Moody
An important determinant of the growth inhibitory activity of indolequinones against pancreatic cancer cells is substitution on the 2-position with 2-unsubstituted derivatives being markedly more potent.
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A novel chemosensor with visible light excitability for sensing Zn2+ in physiological medium and in HeLa cells

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4975-4982
DOI: 10.1039/C4OB00653D, PaperBarun Kumar Datta, Durairaj Thiyagarajan, Soham Samanta, Aiyagari Ramesh, Gopal Das
A highly sensitive, fluorescent, non-cytotoxic turn-on chemosensor with visible light excitability for the detection of intracellular Zn2+ ions.
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A mitochondria-targeted turn-on fluorescent probe based on a rhodol platform for the detection of copper(I)

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4999-5005
DOI: 10.1039/C4OB00527A, PaperMasayasu Taki, Kazushi Akaoka, Koji Mitsui, Yukio Yamamoto
A new spirocyclized rhodol-based fluorescent probe has been developed for detecting mitochondrial Cu+.
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A colorimetric and ratiometric fluorescent probe for distinguishing cysteine from biothiols in water and living cells

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,5023-5030
DOI: 10.1039/C4OB00463A, PaperQingxin Han, Zhaohua Shi, Xiaoliang Tang, Lizi Yang, Zuolin Mou, Jing Li, Jinmin Shi, Chunyang Chen, Wei Liu, Huan Yang, Weisheng Liu
A highly selective merocyanine-based fluorescent probe was developed, which can significantly distinguish Cys from Hcy and GSH by their kinetic profiles in water and respond to the intracellular Cys.
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A study of allosteric binding behaviour of a 1,3-alternate thiacalix[4]arene-based receptor using fluorescence signal

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4917-4923
DOI: 10.1039/C4OB00551A, PaperHirotsugu Tomiyasu, Cheng-Cheng Jin, Xin-Long Ni, Xi Zeng, Carl Redshaw, Takehiko Yamato
The allosteric binding behaviour of a receptor L bearing a 1,3-alternate conformation based thiacalix[4]arene has been evaluated by fluorescence and 1H NMR titration experiments.
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Recent advances in dearomatization of heteroaromatic compounds

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4807-4815
DOI: 10.1039/C4OB00371C, Review ArticleQiuping Ding, Xiaoli Zhou, Renhua Fan
This review summarizes the recent developments in dearomatization reactions of indoles, pyridines, quinolines, isoquinolines, and some other heteroaromatic compounds.
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'Clickable' 2,5-diketopiperazines as scaffolds for ligation of biomolecules: their use in A[small beta] inhibitor assembly

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4964-4974
DOI: 10.1039/C4OB00541D, PaperE. Dufour, L. Moni, L. Bonnat, S. Chierici, J. Garcia
The synthesis of 1,3,6-trisubstituted-2,5-diketopiperazine scaffolds bearing up to three 'clickable' sites for further oxime bond or alkyne-azide cycloaddition ligations is described.
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