Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Catalyst-free reductive amination of aromatic aldehydes with ammonium formate and Hantzsch ester

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01590H, CommunicationPan-Pan Zhao, Xin-Feng Zhou, Jian-Jun Dai, Hua-Jian Xu
Both symmetric and asymmetric aromatic secondary amines were obtained with ammonium formate and Hantzsch ester in the developed protocol.
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The influence of the aromatic aglycon of galactoclusters on the binding of LecA: a case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01599A, PaperFrancesca Casoni, Lucie Dupin, Gerard Vergoten, Albert Meyer, Caroline Ligeour, Thomas Gehin, Olivier Vidal, Eliane Souteyrand, Jean-Jacques Vasseur, Yann Chevolot, Francois Morvan
Mannose-centered galactoclusters exhibiting naphthyl or biphenyl aglycons displayed high affinity for LecA.
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Discovery and synthesis of a novel series of potent, selective inhibitors of the PI3K[small alpha]: 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01589D, PaperYong Yin, Xun Wu, Hong-Wei Han, Shao Sha, She-Feng Wang, Fang Qiao, Ai-Min Lu, Peng-Cheng Lv, Hai-Liang Zhu
A series of novel 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives were synthesized and evaluated for their biological activities. Compound 4l exhibited the most potent and selective activity for PI3K[small alpha].
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A theoretical study of ternary indole-cation-anion complexes

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01879F, PaperJorge A. Carrazana-Garcia, Enrique M. Cabaleiro-Lago, Alba Campo-Cacharron, Jesus Rodriguez-Otero
The simultaneous interactions of an anion and a cation with a [small pi] system were investigated by MP2 and M06-2X theoretical calculations.
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Frustrated Lewis pair catalyzed hydrosilylation and hydrosilane mediated hydrogenation of fulvenes

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01346H, PaperSergej Tamke, Constantin-G. Daniliuc, Jan Paradies
The hydrosilane assisted FLP-catalyzed hydrogenation of pentafulvenes is reported.
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Stereocontrolled lithiation/trapping of chiral 2-alkylideneaziridines: investigation into the role of the aziridine nitrogen stereodynamics

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8505-8511
DOI: 10.1039/C4OB01457J, PaperRosmara Mansueto, Leonardo Degennaro, Jean-Francois Briere, Karen Griffin, Michael Shipman, Saverio Florio, Renzo Luisi
The origin of the stereoselectivity in the lithiation/trapping of 2-alkylideneaziridines bearing a chiral group as the nitrogen substituent was investigated.
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New ganglio-tripod amphiphiles (TPAs) for membrane protein solubilization and stabilization: implications for detergent structure-property relationships

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8480-8487
DOI: 10.1039/C4OB01375A, PaperPil Seok Chae, Hyoung Eun Bae, Muhammad Ehsan, Hazrat Hussain, Jin Woong Kim
This study introduces new ganglio-TPAs with enhanced efficacy for membrane protein solubilization and stabilization compared to conventional detergents.
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Cycloreversion of [small beta]-lactams via photoinduced electron transfer

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8428-8432
DOI: 10.1039/C4OB01416B, PaperRaul Perez-Ruiz, Jose A. Saez, M. Consuelo Jimenez, Miguel A. Miranda
With DABCO as an electron donor, photoinduced cycloreversion of [small beta]-lactams leads to olefins through 1,4-radical anions and 1,4-biradicals as intermediates.
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Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8367-8378
DOI: 10.1039/C4OB01063A, Review ArticleAlexander C. Drohat, Atanu Maiti
We review advances in understanding the mechanism of DNA glycosylases, emphasizing the role of the nucleobase leaving-group.
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Synthesis of L-rhamnose derived chiral bicyclic triazoles as novel sodium-glucose transporter (SGLT) inhibitors

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8415-8421
DOI: 10.1039/C4OB01319K, PaperSiddamal Reddy Putapatri, Abhinav Kanwal, Balasubramanian Sridhar, Sanjay K. Banerjee, Srinivas Kantevari
Fused chiral bicyclic 1,2,3-triazoles synthesized from commercially available natural L-rhamnose exhibited excellent SGLT inhibition activity.
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The first stereoselective total synthesis of neosemburin and isoneosemburin

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8408-8414
DOI: 10.1039/C4OB01239A, PaperGadi Madhusudhan Reddy, Perali Ramu Sridhar
The stereoselective total synthesis of neosemburin and isoneosemburin was achieved using 3-C-branched sugar precursors which in turn were synthesized by Claisen rearrangement of sugar derived allyl vinyl ethers.
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Triflic acid-promoted cycloisomerization of 2-alkynylphenyl isothiocyanates and isocyanates: a novel synthetic method for a variety of indole derivatives

14 October, 2014 - 07:54

Org. Biomol. Chem., 2014, 12,8398-8407
DOI: 10.1039/C4OB00825A, PaperTakao Saito, Yoshihiko Sonoki, Takashi Otani, Noriki Kutsumura
A unique method for synthesis of structurally diverse types of indoles involving a triflic acid-promoted cycloisomerization and a Wagner-Meerwein-type rearrangement is described.
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Design and synthesis of a new dimeric xanthone derivative: enhancement of G-quadruplex selectivity and telomere damage

12 October, 2014 - 07:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01658K, PaperMarco Franceschin, Daniele Nocioni, Annamaria Biroccio, Chiara Cingolani, Emanuela Micheli, Stefano Cacchione, Alessandro Venditti, Pasquale Zizza, Armandodoriano Bianco, alessandro altieri
Following the results we previously reported on a series of xanthene and xanthone derivatives as G-quadruplex stabilizing ligands, in order to obtain a more selective compound with respect to the...
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Synthesis and characterisation of glucosamine-NSAID bioconjugates

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8325-8335
DOI: 10.1039/C4OB01681E, PaperRachel A. Jones, Yann Thillier, Siva S. Panda, Nicole Rivera Rosario, C. Dennis Hall, Alan R. Katritzky
Synthetic strategies to prepare non-steroidal anti-inflammatory drug-glucosamine bioconjugates.
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Synthesis of enantiomerically enriched indolines and tetrahydroisoquinolines from (S)-amino acid-derived chiral carbocations: an easy access to (3S,4R)-demethoxy-3-isopropyl diclofensine

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8318-8324
DOI: 10.1039/C4OB00922C, PaperSudipta Kumar Manna, Gautam Panda
Enantiomerically enriched indolines and tetrahydroisoquinolines were synthesized in high yields from easily accessible (S)-amino acid-derived chiral carbocations.
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Peptidomimetic inhibitors of N-myristoyltransferase from human malaria and leishmaniasis parasites

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8132-8137
DOI: 10.1039/C4OB01669F, CommunicationTayo O. Olaleye, James A. Brannigan, Shirley M. Roberts, Robin J. Leatherbarrow, Anthony J. Wilkinson, Edward W. Tate
Peptidomimetic inhibitors of N-myristoyltransferase from malaria and leishmaniasis parasites have been designed with nanomolar potency, and reveal the first direct structural evidence for a ternary NMT/CoA/myristoyl peptide product complex.
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Performance of DFT methods and origin of stereoselectivity in bipyridine N,N[prime or minute]-dioxide catalyzed allylation and propargylation reactions

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8346-8353
DOI: 10.1039/C4OB01719F, PaperDiana Sepulveda, Tongxiang Lu, Steven E. Wheeler
It is shown that many DFT methods correctly predict the stereoselectivity of bipyridine N,N[prime or minute]-dioxide catalyzed alkylation reactions despite predicting the incorrect low-lying transition state structures. A novel explanation of the origin of stereoselectivity in these reactions is also provided.
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Base-promoted annulation of [small alpha]-hydroxy ketones and dimethyl but-2-ynedioate: straightforward access to pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8128-8131
DOI: 10.1039/C4OB01858C, CommunicationHaitao He, Chaorong Qi, Yanglu Ou, Wenfang Xiong, Xiaohan Hu, Yanwei Ren, Huanfeng Jiang
A novel direct synthesis of pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones from [small alpha]-hydroxy ketones and dimethyl but-2-ynedioate via a base-promoted cascade annulation has been developed.
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Synthesis of substituted azafluorenones from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8138-8141
DOI: 10.1039/C4OB01629G, CommunicationNada Marquise, Vincent Dorcet, Floris Chevallier, Florence Mongin
Auto-tandem processes combining either Suzuki or Heck coupling with direct cyclizing arylation are described.
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Oxidative damage of aromatic dipeptides by the environmental oxidants NO2[radical dot] and O3

10 October, 2014 - 06:54

Org. Biomol. Chem., 2014, 12,8280-8287
DOI: 10.1039/C4OB01577K, PaperL. F. Gamon, J. M. White, U. Wille
Irreversible oxidative damage at both aromatic side chains and dipeptide linkage occurs in aromatic N- and C-protected dipeptides upon exposure to the environmental pollutants NO2[radical dot] and O3.
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