Royal Society of Chemistry

Unprecedented One-Pot Sequential Thiolate Substitutions of 8-methylthio-BODIPY under Mild Conditions leading to a Red Emissive BODIPY Dye 3,5,8-tris(PhS)-BODIPY.

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01892C, CommunicationKeith Pannell, Alejandro Jose Metta Magana, Eduardo Pena-Cabrera, Robinson Roacho
The simple reaction of phenylthiol with 8-MeS-BODIPY (1) in dichloromethane was readily accomplished to form 8-PhS-BODIPY (2). If the reaction is performed in THF 3,8-bis(phenylthio)-BODIPY (3) and 3,5,8-tris(phenylthio)-BODIPY (4) are...
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Sulfate recognition by a hexaaza cryptand receptor

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02027H, PaperPedro Mateus, Rita Delgado, Vania Andre, M. Teresa Duarte
A polypyrrolic polyammonium macrobicycle encapsulates sulfate with very high association constants and selectivity in the presence of other anions.
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The synthesis of [18F]pitavastatin as a tracer for hOATP using the Suzuki coupling

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01953A, PaperYusuke Yagi, Hiroyuki Kimura, Kenji Arimitsu, Masahiro Ono, Kazuya Maeda, Hiroyuki Kusuhara, Tetsuya Kajimoto, Yuichi Sugiyama, Hideo Saji
Fluorine-18 labeled radiotracers, such as [18F]fluorodeoxyglucose, can be used as practical diagnostic agents in positron emission tomography (PET). Furthermore, the properties of pharmaceuticals can be enhanced significantly by the introduction...
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Studies Towards Asymmetric Synthesis of 4(S)-11-Dihydroxydocosahexaenoic acid (diHDHA) Featuring Cross-Coupling of Chiral Stannane under Mild Conditions

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02324B, CommunicationRUI WANG, John Falck
The presented discoveries herein is to utilize the mild Stille coupling reactions of chiral [small alpha]-generated stannane, which is previously developed by our group. We subsequently assembled these three segments and...
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The Development of a Complementary Pathway for the Synthesis of Aliskiren

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01963F, PaperFu-She Han, Le-Le Li, Jin-Ying Ding, Lianxun Gao
The synthesis of aliskiren (1), a recently marketed drug for the treatment of hypertensive disease, is presented. The focus of our synthetic effort is the development of an efficient pathway...
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Synthesis of (phosphonomethyl)phosphinate pyrophosphate analogues via the phospha-Claisen condensation

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02007C, PaperFabien Gelat, Claire Lacomme, Olivier Berger, Laurent Gavara, J.-L. Montchamp
Pyrophosphate analogues are of great importance especially for the design of biologically active molecules.
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Multivalent helix mimetics for PPI-inhibition

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02066A, PaperAnna Barnard, Jennifer A. Miles, George M. Burslem, Amy M. Barker, Andrew J. Wilson
A multivalent helix mimetic is developed that inhibits the p53/hDM2 and induces dimerization/aggregation of its target - hDM2.
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Rapid synthesis of isoquinolinones by intramolecular coupling of amides and ketones

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01948B, PaperWen-Tao Wei, Yu Liu, Lin-Miao Ye, Rong-Hui Lei, Xue-Jing Zhang, Ming Yan
Isoquinolinones were prepared in good yields via the intramolecular coupling of amides and ketones in the presence of KOt-Bu/DMF.
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Characterizations of cationic [gamma]-carbolines binding with double-stranded DNA by spectroscopic methods and AFM imaging

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01905A, PaperTao Jia, Jing Wang, Peng GUO, Junping Yu
Two cationic [gamma]-carbolines, MPII and DPII, were synthesized, and the DNA binding properties of the cationic [gamma]-carbolines were elucidated. Through a series of experiments, we proved that the two cationic...
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[gamma]-CYCLODEXTRIN MODULATES CHEMICAL REACTIVITY BY MULTIPLE COMPLEXATION

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02113D, PaperLuis Garcia Rio, Josefa Fernandez-Rosas, Marcia Pessego, Marjorie Cepeda, Nuno Basilio, Mercedes Parajo, Pedro Rodriguez-Dafonte
Multiple complexation by [gamma]-CD have been studied both by self-diffusion coefficients (DOSY) and chemical kinetic experiments (using 4-methoxybenzenesulfonyl chloride, MBSC, solvolysis as a chemical probe). Surfactant addition as third component...
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Formation of the steroidal C-25 chiral center via the asymmetric alkylation methodology

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02123A, PaperYu. V. Ermolovich, V. N. Zhabinskii, V. A. Khripach
A novel approach for the preparation of steroids containing a chiral center at C-25 is reported. The key stereochemistry inducing step was asymmetric alkylation of pseudoephenamine amides of steroidal C-26 acids. The developed methodology was successfully applied to the synthesis of (25R)- and (25S)-cholestenoic acids as well as (25R)- and (25S)-26-hydroxy brassinolides.
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Synthesis and the absolute configuration of both enantiomers of 4,5-dihydroxy-3-(formyl)cyclopent-2-enone acetonide as a new chiral building block for prostanoid synthesis

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01535E, PaperBeata Lukasik, Marian Mikolajczyk, Grzegorz Bujacz, Remigiusz Zurawinski
Starting from optically inactive meso-tartaric acid (6) the synthesis of both enantiomers of a new cyclopentenone building block 5 was developed.
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Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C-H of acetonitrile and the sp2 C-H of the phenyl group

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02172J, CommunicationChangduo Pan, Honglin Zhang, Chengjian Zhu
Radical cyanomethylation/arylation of arylacrylamides to access oxindoles with acetonitrile as a radical precursor is described, involving dual C-H bond functionalization.
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A QSAR study on the inhibition mechanism of matrix metalloproteinase-12 by arylsulfone analogs based on molecular orbital calculations

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01843E, PaperSeiji Hitaoka, Hiroshi Chuman, Kazunari Yoshizawa
The inhibition mechanism of matrix metalloproteinase-12 by arylsulfone analogs is revealed using a comprehensive computational approach including docking simulations, molecular orbital calculations, and QSAR.
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Design and Synthesis of Troger's Base Ditopic Receptors: Host-Guest Interactions, a Combined Theoretical and Experimental Study

Org. and Biomol. Chem. - 21 November, 2014 - 16:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02266A, PaperManjula Alla, Bhaskar Reddy Manda, Shailaja Myadaraboina, J. Richard Premkumar, G. Narahari Sastry, Sirisha Katkuri, Sarma VS Akella
Two flexible Troger's base ditopic receptors C4TB and C5TB incorporating monoaza crown ether were designed and synthesized for bisammonium ion complexation. Comprehensive study of host-guest interactions were established by 1H...
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Quinoline-derived two-photon sensitive quadrupolar probes

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,9899-9908
DOI: 10.1039/C4OB01551G, PaperPetra Dunkel, Christine Tran, Thibault Gallavardin, Hamid Dhimane, David Ogden, Peter I. Dalko
Quadrupolar 8-dimethylaminoquinoline-derived photosensitive probes underwent photolysis under UV (365 nm) and NIR (730 nm two-photon (TP)) irradiation conditions.
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A facile approach to spirocyclic 2-azido indolines via azidation of indoles with ceric ammonium nitrate

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,9769-9772
DOI: 10.1039/C4OB01549E, CommunicationJing Li, Mao Liu, Qi Li, Hua Tian, Yian Shi
This paper describes azidation of indoles with NaN3 and ceric ammonium nitrate (CAN), giving a variety of spirocyclic 2-azido indolines in good yields and moderate diastereoselectivities.
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Enantioselective synthesis of [small alpha]-benzylated lanthionines and related tripeptides for biological incorporation into E. coli peptidoglycan

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,9853-9863
DOI: 10.1039/C4OB01476F, PaperThibaut Denoel, Astrid Zervosen, Christian Lemaire, Bernard Joris, Mireille Herve, Didier Blanot, Guillermo Zaragoza, Andre Luxen
The synthesis of modified tripeptides (S)-Ala-[gamma]-(R)-Glu-X, where X = (R,S) or (R,R) diastereomers of [small alpha]-benzyl or [small alpha]-(4-azidobenzyl)lanthionine, was carried out.
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Design and synthesis of a mitochondria-targeting carrier for small molecule drugs

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,9793-9796
DOI: 10.1039/C4OB01981D, CommunicationJunyan Han, Tae Hoon Lee, Ching-Hsuan Tung, Daniel Y. Lee
A novel mitochondria-targeting carrier QCy7HA was developed, which transported the covalently attached doxorubicin (DOX) to mitochondria specifically, resulting in the limitation of the effects of P-glycoprotein efflux pumps of multidrug-resistant cells on DOX.
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Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones

Org. and Biomol. Chem. - 21 November, 2014 - 16:17

Org. Biomol. Chem., 2014, 12,9786-9788
DOI: 10.1039/C4OB02131B, CommunicationAlexander V. Aksenov, Alexander N. Smirnov, Nicolai A. Aksenov, Inna V. Aksenova, Asiyat S. Bijieva, Michael Rubin
A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
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