Royal Society of Chemistry

An acridinium-based sensor as a fluorescent photoinduced electron transfer probe for proton detection modulated by anionic micelles

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00559G, PaperStefano Basili, Tiziana Del Giacco, Fausto Elisei, Raimondo Germani
Photoinduced electron transfer has been demonstrated to be the quenching mechanism for the fluorescent pH sensor based on the 9-amino-10-methylacridinium chromophore. The presence of anionic micelles causes a significant increase in the detection sensitivity of pH.
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SN2 regioselectivity in the esterification of 5- and 7-membered azacycloalkane quaternary salts: a DFT study to reveal the transition state ring conformation prevailing over the ground state ring strain

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00695J, PaperAkihiro Kimura, Susumu Kawauchi, Takuya Yamamoto, Yasuyuki Tezuka
SN2 regioselectivity in 5- and 7-membered azacycloalkanes quaternary salts is directed by the transition state ring conformation.
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Synthesis and evaluation of antineurotoxicity properties of an amyloid-[small beta] peptide targeting ligand containing a triamino acid

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00959B, PaperDmytro Honcharenko, Partha Pratim Bose, Jyotirmoy Maity, Firoz Roshan Kurudenkandy, Alok Juneja, Erik Floistrup, Henrik Biverstal, Jan Johansson, Lennart Nilsson, Andre Fisahn, Roger Stromberg
A new triamino acid enables synthesis of an amyloid-[small beta] peptide (A[small beta]) targeting ligand with additional A[small beta]-ligand interactions that gives protection towards A[small beta]-induced reduction of gamma oscillations in hippocampal slice preparation.
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Convenient access to readily soluble symmetrical dialkyl-substituted [small alpha]-oligofurans

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00898G, PaperEdward E. Korshin, Gregory M. Leitus, Michael Bendikov
A combination of heteroatom directed lithiation/CuCl2-induced homocoupling, Wittig olefination/Pd-catalyzed transfer hydrogenation followed by Suzuki-Miyaura or Stille cross-coupling enables convenient access to dialkyl-substituted [small alpha]-oligofurans of potential interest for organic electronics.
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Iron-catalyzed tetrasubstituted alkene formation from alkynes and sodium sulfinates

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6076-6079
DOI: 10.1039/C4OB00816B, CommunicationSaiwen Liu, Lichang Tang, Hui Chen, Feng Zhao, Guo-Jun Deng
An iron-catalyzed sulfenylation and arylation of alkynes with aryl sulfinic acid sodium salts is described.
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Synthesis of methyl 2-cyano-3,12-dioxo-18[small beta]-olean-1,9(11)-dien-30-oate analogues to determine the active groups for inhibiting cell growth and inducing apoptosis in leukemia cells

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00703D, PaperXiaojing Li, Yuetong Wang, Yuan Gao, Lei Li, Xin Guo, Dan Liu, Yongkui Jing, Linxiang Zhao
A series of CDODO-Me-12 analogues were synthesized with improved ability to inhibit cell growth and induce apoptosis in HL-60 cells.
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Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6190-6199
DOI: 10.1039/C4OB01088D, PaperDavid E. Stephens, Gabriel Chavez, Martin Valdes, Monica Dovalina, Hadi D. Arman, Oleg V. Larionov
Novel and efficient method of direct perfluoroalkylation of azine N-oxides has been developed and interesting mechanistic details have been provided.
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Desilylative activation of TMSCN in chemoselective Strecker-Ugi type reaction: functional fused imidazoles as building blocks as an entry route to annulated purines

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00882K, PaperSankar K. Guchhait, Vikas Chaudhary
Nucleophilic activation of TMSCN as an isocyanide equivalent by DABCO-THF in the Strecker-Ugi reaction facilitates the synthesis of functional imidazoles which, as building blocks, afford access to C8-N9 annulated purines.
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Balanced [small pi]-[small pi] interactions directing the self-assembly of indolocarbazole-based low molecular mass organogelators

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6134-6144
DOI: 10.1039/C4OB00873A, PaperPeng Gong, Pengchong Xue, Chong Qian, Zhenqi Zhang, Ran Lu
New indolocarbazole-based organogelators emitting strong blue light have been synthesized.
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Catalyst-free activation of methylene chloride and alkynes by amines in a three-component coupling reaction to synthesize propargylamines

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00986J, PaperVikas S. Rawat, Thulasiram Bathini, S. Govardan, Bojja Sreedhar
Propargylamines are synthesized via metal-free activation of the C-halogen bond of dihalomethanes and the C-H bond of terminal alkynes in a three-component coupling without catalyst or additional base and under mild reaction conditions.
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Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6151-6166
DOI: 10.1039/C4OB00841C, PaperTran Quang Hung, Do Huy Hoang, Ngo Ngoc Thang, Tuan Thanh Dang, Khurshid Ayub, Alexander Villinger, Aleksej Friedrich, Stefan Lochbrunner, Gerd-Uwe Flechsig, Peter Langer
A series of indolo[2,3-b]quinoxaline derivatives were efficiently synthesized from 2,3-dibromoquinoxaline by two pathways.
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Mutation of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase at Trp-110 affects stereoselectivity of aromatic ketone reduction

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5905-5910
DOI: 10.1039/C4OB00794H, PaperJay M. Patel, Musa M. Musa, Luis Rodriguez, Dewey A. Sutton, Vladimir V. Popik, Robert S. Phillips
Secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus was mutated at Trp-110, and mutant enzymes with high activity and high stereoselectivity for aromatic ketone reduction were identified.
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Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6175-6180
DOI: 10.1039/C4OB00946K, PaperJeannette T. Bowler, Freeman M. Wong, Scott Gronert, James R. Keeffe, Weiming Wu
The nucleophilic aromatic substitution reactions of piperidine with N-methylpyridinium ions in methanol occur via rate determining preassociation of a second piperidine molecule with the addition intermediate followed by barrier-free deprotonation. Loss of leaving group is concurrent with deprotonation for Cl, Br, and I (E2), but subsequent to deprotonation, although rapid, for CN and F (E1cBIRR).
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Synthesis, and the antioxidant, neuroprotective and P-glycoprotein induction activity of 4-arylquinoline-2-carboxylates

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6267-6277
DOI: 10.1039/C4OB00488D, PaperJaideep B. Bharate, Abubakar Wani, Sadhana Sharma, Shahi Imam Reja, Manoj Kumar, Ram A. Vishwakarma, Ajay Kumar, Sandip B. Bharate
An efficient synthesis of 4-arylquinoline-2-carboxylates and their antioxidant, neuroprotective and P-glycoprotein induction activity have been described.
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6-Azido hyacinthacine A2 gives a straightforward access to the first multivalent pyrrolizidine architectures

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6250-6266
DOI: 10.1039/C4OB01117A, PaperGiampiero D'Adamio, Camilla Parmeggiani, Andrea Goti, Antonio J. Moreno-Vargas, Elena Moreno-Clavijo, Inmaculada Robina, Francesca Cardona
The synthesis of the first multivalent pyrrolizidine iminosugars is reported, with up to 9 bioactive molecules on the same scaffold.
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Design and synthesis of (S)- and (R)-[small alpha]-(phenyl)ethylamine-derived NH-type ligands and their application for the chemical resolution of [small alpha]-amino acids

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6239-6249
DOI: 10.1039/C4OB00669K, PaperRyosuke Takeda, Akie Kawamura, Aki Kawashima, Hiroki Moriwaki, Tatsunori Sato, Jose Luis Acena, Vadim A. Soloshonok
A chiral ligand reacts with racemic amino acids to produce easily separable Ni(II) complexes which can be disassembled to afford both enantiomers of target amino acids.
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Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5990-5994
DOI: 10.1039/C4OB01265H, PaperMalik Hellal, Florian C. Falk, Elena Wolf, Marian Dryzhakov, Joseph Moran
B(C6F5)3 possesses a different reactivity/chemoselectivity profile than traditional Lewis and Bronsted acids and is effective at enabling catalytic SN1 reactions of alcohols in the presence of acid sensitive groups without compromising reaction rates, substrate scope or catalyst loadings.
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Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to [small beta],[small beta]-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5883-5890
DOI: 10.1039/C4OB01085J, PaperJeffrey Buter, Renee Moezelaar, Adriaan J. Minnaard
Palladium catalyzed asymmetric conjugate addition of ortho-substituted arylboronic acids to cyclic enones and its application in natural product synthesis.
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Copper(I)-induced amplification of a [2]catenane in a virtual dynamic library of macrocyclic alkenes

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,6167-6174
DOI: 10.1039/C4OB01009D, PaperJose Augusto Berrocal, Marko M. L. Nieuwenhuizen, Luigi Mandolini, E. W. Meijer, Stefano Di Stefano
The interlocked virtual component 1 of a well-behaved dynamic library of cyclic olefins is resuscitated by means of the template effect.
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Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents

Org. and Biomol. Chem. - 27 July, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,5995-6004
DOI: 10.1039/C4OB00830H, PaperXiaoli Wang, Linna Wang, Xiao Sheng, Zhangjian Huang, Tingting Li, Ming Zhang, Jinyi Xu, Hui Ji, Jian Yin, Yihua Zhang
Compound 8e protected against the collagen and adrenaline induced thrombosis in mice, and exhibited greater antithrombotic activity than NBP and aspirin in rats.
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