Royal Society of Chemistry
Silanization of quartz, silicon and mica surfaces with light-driven molecular motors: construction of surface-bound photo-active nanolayers
DOI: 10.1039/C3OB40276B, PaperGabor London, Gregory T. Carroll, Ben L. Feringa
The attachment of molecular rotary motors containing triethoxysilane functional groups to quartz, silicon and mica surfaces is described and the effect of photochemical and thermal isomerization steps on the surface assemblies was studied.
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An efficient coupling of N-tosylhydrazones with 2-halopyridines: synthesis of 2-[small alpha]-styrylpyridines endowed with antitumor activity
DOI: 10.1039/C3OB40263K, PaperMarie Lawson, Abdallah Hamze, Jean-Francois Peyrat, Jerome Bignon, Joelle Dubois, Jean-Daniel Brion, Mouad Alami
PdCl2(MeCN)2 in combination with DPPF or tBu2MeP-HBF4 catalyzes the reaction of N-tosylhydrazones with various 2-halopyridines to provide the 2-alpha-styrylpyridines olefins of biological interest.
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Four-component assembly in the crystalline state driven by amidinium-carboxylate salt bridge formation from an aqueous solution
DOI: 10.1039/C3OB40309B, PaperTakahiro Kusukawa, Kazuya Matsumoto, Hajime Nakamura, Wataru Iizuka, Keisuke Toyama, Shota Takeshita
The introduction of two amidinium groups to the 1,8-position of a spacer unit can control the direction of formation of a self-assembled structure and succeeded in the formation of a four-component assembled structure .
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Synthesis and biological evaluation of benzo[a]phenazine derivatives as a dual inhibitor of topoisomerase I and II
DOI: 10.1039/C3OB40325D, PaperShi-Tian Zhuo, Chun-Yan Li, Ming-Hao Hu, Shuo-Bin Chen, Pei-Fen Yao, Shi-Liang Huang, Tian-Miao Ou, Jia-Heng Tan, Lin-Kun An, Ding Li, Lian-Quan Gu, Zhi-Shu Huang
A series of new benzo[a]phenazine derivatives were synthesized and found to be a rare class of Topo I poisons and Topo II catalytic inhibitors.
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Convergent approach to complex spirocyclic pyrans: practical synthesis of the oxa-pinnaic acid core
DOI: 10.1039/C3OB40284C, PaperFrank D. Ferrari, Adele E. Pasqua, Andrew J. Ledgard, Rodolfo Marquez
One stereocentre to rule them all. The enantioselective synthesis of the oxa-pinnaic acid framework was achieved through internal asymmetric induction.
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Tautomerism and metal complexation of 2-acylmethyl-2-oxazolines: a combined synthetic, spectroscopic, crystallographic and theoretical treatment
DOI: 10.1039/C3OB25867J, PaperRoderick C. Jones, Khrystyna Herasymchuk, Tayseer Mahdi, Anna Petrov, Sanja Resanovic, Douglas G. Vaughan, Alan J. Lough, J. Wilson Quail, Bryan D. Koivisto, R. Stephen Wylie, Robert A. Gossage
A synthetic, structural and theoretical investigation into the solid-state, solution and gas phase structure(s) of six 2-acylmethyl-4,4-dimethyl-2-oxazolines is reported.
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One-shot preparation of an inherently chiral trifunctional calix[4]arene from an easily available cone-triformylcalix[4]arene
DOI: 10.1039/C3OB40355F, PaperMaria Ciaccia, Irene Tosi, Roberta Cacciapaglia, Alessandro Casnati, Laura Baldini, Stefano Di Stefano
An inherently chiral ABCH-substituted cone-calix[4]arene derivative has been prepared in a one-step process starting from the easily available cone-triformylcalix[4]arene.
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Strand breakage of a (6-4) photoproduct-containing DNA at neutral pH and its repair by the ERCC1-XPF protein complex
DOI: 10.1039/C3OB00012E, PaperNorihito Arichi, Junpei Yamamoto, Chiaki Takahata, Emi Sano, Yuji Masuda, Isao Kuraoka, Shigenori Iwai
The (6-4) photoproduct in DNA is heat-labile at neutral pH, while its Dewar valence isomer is relatively stable. ERCC1-XPF removes the 3[prime or minute]-blocking end in the presence of RPA.
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A convenient method for selective detection of 5-hydroxymethylcytosine and 5-formylcytosine sites in DNA sequences
DOI: 10.1039/C3OB40447A, PaperWuxiang Mao, Jianlin Hu, Tingting Hong, Xiwen Xing, Sen Wang, Xi Chen, Xiang Zhou
The 5fC and 5hmC could be detected respectively, by comparing the DNA treated with piperidine with and without oxidation.
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Symmetric and unsymmetric 3,3[prime or minute]-linked bispyrroles via ring-enlargement reactions of furan-derived donor-acceptor cyclopropanes
DOI: 10.1039/C3OB40228B, PaperJohannes Kaschel, Tobias F. Schneider, Daniel Kratzert, Dietmar Stalke, Daniel B. Werz
Highly substituted symmetric and unsymmetric 3,3[prime or minute]-linked bispyrroles were obtained by a short sequence starting from furan utilizing donor-acceptor cyclopropanes as key intermediates.
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Synthesis of chondroitin/dermatan sulfate-like oligosaccharides and evaluation of their protein affinity by fluorescence polarization
DOI: 10.1039/C3OB40306H, PaperSusana Maza, M. Mar Kayser, Giuseppe Macchione, Javier Lopez-Prados, Jesus Angulo, Jose L. de Paz, Pedro M. Nieto
A novel strategy for the synthesis of chondroitin/dermatan sulfate-like oligosaccharides is described. The binding affinities of the synthesized compounds to FGF-2 are estimated by using a fluorescence polarization assay.
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Aqueous SDS micelle-promoted acid-catalyzed domino ABB[prime or minute] imino Diels-Alder reaction: a mild and efficient synthesis of privileged 2-methyl-tetrahydroquinoline scaffolds
DOI: 10.1039/C3OB40171E, PaperDiego R. Merchan Arenas, Carlos A. Martinez Bonilla, Vladimir V. Kouznetsov
A new green and efficient synthesis of cis 4-amido-N-yl-2-methyl-1,2,3,4-tetrahydroquinolines through domino type ABB[prime or minute] imino Diels-Alder reaction in acidified aqueous-SDS surfactant was developed.
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Efficient pseudo-five-component coupling-Fiesselmann synthesis of luminescent oligothiophenes and their modification
DOI: 10.1039/C3OB40124C, PaperMarco Teiber, Sonke Giebeler, Timo Lessing, Thomas J. J. Muller
Highly luminescent symmetrical terthiophenes and quinquethiophenes are accessible in a consecutive pseudo-five-component reaction in good to excellent yield.
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Synthesis of tetrasubstituted benzenes via rhodium(I)-catalysed ring-opening benzannulation of cyclobutenols with alkynes
DOI: 10.1039/C3OB40436F, CommunicationTakanori Matsuda, Norio Miura
A simple and efficient method has been developed for the synthesis of 1,2,3,5-tetrasubstituted benzenes via rhodium(I)-catalysed ring-opening benzannulation of 1,3-disubstituted cyclobutenols with internal alkynes.
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Towards a dynamic covalent molecular switch: substituent effects in chalcone/flavanone isomerism
DOI: 10.1039/C3OB40467F, CommunicationJesse Mai, Ermal Hoxha, Caitlin E. Morton, Brian M. Muller, Marc J. Adler
Chalcone/flavanone interconversion occurs facilely under aqueous alkaline conditions making it a promising scaffold for the development of a covalent molecular switch.
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Total synthesis and biological evaluation of (-)-exiguolide analogues: importance of the macrocyclic backbone
DOI: 10.1039/C3OB40131F, PaperHaruhiko Fuwa, Kana Mizunuma, Makoto Sasaki, Takaya Suzuki, Hiroshi Kubo
Synthesis and biological evaluation of (-)-exiguolide analogues elucidated the importance of the macrocyclic backbone for antiproliferative activity and the tolerance of the side chain to structural modifications.
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Formation, structure, and reactivity of meso-tetraaryl-chlorolactones, -porpholactams, and -chlorolactams, porphyrin and chlorin analogues incorporating oxazolone or imidazolone moieties
DOI: 10.1039/C3OB40138C, PaperJoshua Akhigbe, John Haskoor, Jeanette A. Krause, Matthias Zeller, Christian Bruckner
An hydrazine-induced O-to-N exchange in porpholactones forms porpholactams; a concomitant reduction generates the chlorin analogues chlorolactone and chlorolactam; further manipulations generates imidazoloporphyrins.
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CAL-B catalyzed desymmetrization of 3-alkylglutarate: "olefin effect" and asymmetric synthesis of pregabalin
DOI: 10.1039/C3OB40311D, PaperJae-Hoon Jung, Doo-Ha Yoon, Philjun Kang, Won Koo Lee, Heesung Eum, Hyun-Joon Ha
CAL-B catalyzed desymmetrization of prochiral 3-alkylglutaric acid diesters was performed to prepare optically active 3-alkylglutaric acid monoesters bearing various alkyl substituents, including methyl, ethyl, propyl and allyl groups.
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Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine
DOI: 10.1039/C3OB27390C, PaperHogyu Lee, Jun Hee Kim, Won Koo Lee, Jaeheung Cho, Wonwoo Nam, Jaedeok Lee, Hyun-Joon Ha
Azafuranoses represented by the natural product (+)-2,5-imino-2,5,6-trideoxy-gulo-heptitol and its C(3)-epimer were elaborated from a commercially available enantiomerically pure (2R)-hydroxymethylaziridine by highly stereoselective directed reactions..
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Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity
DOI: 10.1039/C3OB27513B, PaperDebashis Ghosh, Debashis Sahu, S. Saravanan, Sayed H. R. Abdi, Bishwajit Ganguly, Noor-ul H. Khan, Rukhsana I. Kureshy, Hari C. Bajaj
Chirally enriched homoallyl alcohols were effectively synthesized by using synthetically amenable organocatalyst derived from L-phenylalanine.
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