Royal Society of Chemistry

"AND" luminescent "reactive" molecular logic gates: a gateway to multi-analyte bioimaging and biosensing

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1294-1306
DOI: 10.1039/C4OB02076F, Review ArticleAnthony Romieu
This feature article focuses on the recent development of "AND" luminescent molecular logic gates, in which the optical output is produced in response to multiple (bio)chemical inputs and through cascades of covalent bond-modifying reactions triggered by target (bio)analytes, for biosensing and bioimaging applications in complex media.
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Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis-Sonogashira coupling sequence

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1571-1576
DOI: 10.1039/C4OB02386B, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Sidra Hassan, Anja Ullrich, Thomas J. J. Muller
(Hetero)arylated propargyl amides are efficiently prepared by consecutive chemoenzymatic three-component synthesis based upon lipase catalyzed aminolysis followed by Sonogashira coupling.
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E- or Z-Selective synthesis of 4-fluorovinyl-1,2,3-triazoles with fluorinated second-generation Julia-Kocienski reagents

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1536-1549
DOI: 10.1039/C4OB02179G, PaperRakesh Kumar, Govindra Singh, Louis J. Todaro, Lijia Yang, Barbara Zajc
Second-generation Julia-Kocienski reagents from CuAAC reactions of [small alpha]-fluoropropargyl benzothiazole sulfone with azides, react with aldehydes and ketones to give N-substituted 4-(1-fluorovinyl)triazoles. Reactions of aldehydes can be tuned towards E or Z-alkenes selectively.
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Stereoselective synthesis of fluorinated aminoglycosyl phosphonates

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1317-1321
DOI: 10.1039/C4OB02317J, CommunicationSanne Bouwman, Romano V. A. Orru, Eelco Ruijter
We report the highly stereoselective addition of lithiated difluorophosphonates to nitroglycals, providing synthetic access to biologically relevant fluorinated aminoglycosyl phosphonates.
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Synthesis and antimalarial evaluation of amide and urea derivatives based on the thiaplakortone A natural product scaffold

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1558-1570
DOI: 10.1039/C4OB01849D, PaperBrett D. Schwartz, Tina S. Skinner-Adams, Katherine T. Andrews, Mark J. Coster, Michael D. Edstein, Donna MacKenzie, Susan A. Charman, Maria Koltun, Scott Blundell, Anna Campbell, Rebecca H. Pouwer, Ronald J. Quinn, Karren D. Beattie, Peter C. Healy, Rohan A. Davis
A series of amide and urea analogues based on the thiaplakortone A natural product scaffold were synthesised and screened for in vitro antimalarial activity.
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Linear dialdehydes as promising substrates for aminocatalyzed transformations

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1280-1293
DOI: 10.1039/C4OB01805B, Review ArticleIndresh Kumar, Panduga Ramaraju, Nisar A. Mir, Anoop Singh
Linear dialdehydes: This article summarizes the recent utilization of linear dialdehydes as appropriate substrates for amine catalyzed cascade/domino transformations.
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Synthesis and antitumor activity of novel 2-substituted indoline imidazolium salt derivatives

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1550-1557
DOI: 10.1039/C4OB02385D, PaperXiao-Liang Xu, Chun-Lei Yu, Wen Chen, Ying-Chao Li, Li-Juan Yang, Yan Li, Hong-Bin Zhang, Xiao-Dong Yang
A series of novel 2-substituted indoline imidazolium salt derivatives were synthesized and their antitumor structure-activity relationship studies were reported.
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N-heterocyclic carbene-catalyzed cyclocondensation of 2-aryl carboxylic acids and enones: highly enantioselective synthesis of [small delta]-lactones

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1313-1316
DOI: 10.1039/C4OB02330G, CommunicationJin-Tang Cheng, Xiang-Yu Chen, Song Ye
The NHC-catalyzed [4 + 2] cyclocondensation of 2-aryl carboxylic acids with enones was developed, giving [small delta]-lactones in good yields with high enantioselectivities.
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Pd-catalyzed Heck-conjoined amidation and concomitant chemoselective Michael-addition: an efficient tandem approach to highly functionalized tetrahydroquinazolines from o-haloanilines

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1521-1530
DOI: 10.1039/C4OB02286F, PaperRakesh K. Saunthwal, Monika Patel, Abhinandan K. Danodia, Akhilesh K. Verma
Efficient palladium-catalyzed tandem approach for the synthesis of highly functionalized tetrahydroquinazolines from o-haloanilines with acrylates and isothiocyanates/isocyanates via Heck-conjoined amidation/thioamidation and concomitant chemoselective Michael-addition is described.
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A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1515-1520
DOI: 10.1039/C4OB02147A, PaperShuo Xing, James L. Gleason
Glycal etherification followed by azidonitration/reduction solves a difficult SN2 step in the synthesis of N-glycolyl muramyl dipeptide.
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Domino reaction involving the Bestmann-Ohira reagent and [small alpha],[small beta]-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1492-1499
DOI: 10.1039/C4OB02365J, PaperShakir Ahamad, Ashis Kumar Gupta, Ruchir Kant, Kishor Mohanan
A mild, efficient and rapid domino reaction involving the Bestmann-Ohira reagent (BOR) and [small alpha],[small beta]-unsaturated aldehydes has been developed for the synthesis of densely functionalized vinylpyrazoles.
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A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: design, synthesis, and biological evaluation

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1507-1514
DOI: 10.1039/C4OB01605J, PaperGaofei Wei, Weijing Luan, Shuai Wang, Shanshan Cui, Fengran Li, Yongxiang Liu, Yang Liu, Maosheng 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.
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Accelerated Fmoc solid-phase synthesis of peptides with aggregation-disrupting backbones

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1500-1506
DOI: 10.1039/C4OB02260B, PaperYi-Chao Huang, Chao-Jian Guan, Xiang-Long Tan, Chen-Chen Chen, Qing-Xiang Guo, Yi-Ming Li
In this work, we describe an accelerated solid-phase synthetic protocol for ordinary or difficult peptides involving air-bath heating and amide protection.
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Stereodivergent synthesis of the LFA-1 antagonist BIRT-377 by porcine liver esterase desymmetrization and Curtius rearrangement

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1463-1469
DOI: 10.1039/C4OB02303J, PaperAaron Johnson, Matthew J. Saunders, Thomas G. Back
BIRT-377 was synthesized by enzymatic desymmetrization in conjunction with Curtius rearrangement, affording a key [small alpha]-quaternary amine intermediate in high ee.
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Enzyme-triggered delivery of chlorambucil from conjugates based on the cell-penetrating peptide BP16

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1470-1480
DOI: 10.1039/C4OB01875C, PaperMarta Soler, Marta Gonzalez-Bartulos, Eduard Figueras, Xavi Ribas, Miquel Costas, Anna Massaguer, Marta Planas, Lidia Feliu
The combination of the cell-penetrating peptide BP16 with the enzymatic cleavable sequence Gly-Phe-Leu-Gly constitutes a drug delivery system for the effective uptake and release of chlorambucil in cancer cells.
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Cu-catalyzed arylation of the amino group in the indazole ring: regioselective synthesis of pyrazolo-carbazoles

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1481-1491
DOI: 10.1039/C4OB02044H, PaperK. Anil Kumar, Prakash Kannaboina, Devendra K. Dhaked, Ram A. Vishwakarma, Prasad V. Bharatam, Parthasarathi Das
Arylated aminoindazoles were synthesized by copper-catalyzed C-N bond cross-coupling with boronic acids. These were then transformed to pyrazolo-carbazoles by Pd-catalyzed regioselective cross-dehydrogenative coupling.
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Unraveling the contributions of hydrogen-bonding interactions to the activity of native and non-native ligands in the quorum-sensing receptor LasR

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1453-1462
DOI: 10.1039/C4OB02252A, PaperJoseph P. Gerdt, Christine E. McInnis, Trevor L. Schell, Helen E. Blackwell
Systematic analyses of mutant LasR quorum-sensing receptors with its native ligand and a suite of synthetic analogues reveal the importance of specific polar interactions for native receptor activation.
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The development and use of a general route to brassinolide, its biosynthetic precursors, metabolites and analogues

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1446-1452
DOI: 10.1039/C4OB02197E, PaperA. L. Hurski, Yu. V. Ermolovich, V. N. Zhabinskii, V. A. Khripach
A new method for the construction of steroid side chains through the addition of lithium salts of dithianes to a C-22 aldehyde was developed. It was applied for the preparation of brassinolide and related brassinosteroids.
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Tris(triazole) tripodal receptors as selective probes for citrate anion recognition and multichannel transition and heavy metal cation sensing

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1429-1438
DOI: 10.1039/C4OB02135E, PaperMaria del Carmen Gonzalez, Francisco Oton, Arturo Espinosa, Alberto Tarraga, Pedro Molina
The preparation and binding properties towards citrate anions and cations of two three-armed triazole based receptors are described.
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Manganese triacetate as an efficient catalyst for bisperoxidation of styrenes

Org. and Biomol. Chem. - 27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1439-1445
DOI: 10.1039/C4OB01823K, PaperAlexander O. Terent'ev, Mikhail Yu. Sharipov, Igor B. Krylov, Darya V. Gaidarenko, Gennady I. Nikishin
Bisperoxidation of styrenes with tert-butyl hydroperoxide in the presence of a catalytic amount of Mn(OAc)3.
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