54005-84-4Relevant academic research and scientific papers
69. Functionalized Nitroalkanes in Organic Synthesis. The First Concise Preparation of 4-Hydroxyheptadecan-7-one and 14-Hydroxyoctadecan-8-one, Two New Hydroxy Ketones Isolated from Chiococca alba
Ballini, Roberto,Bosica, Giovanna,Rafaiani, Gianni
, p. 879 - 882 (1995)
The 4-hydroxyheptadecan-7-one (1) and 14-hydroxyoctadecan-8-one (2), two new hydroxyketones isolated from leaves of Chiococca alba, were synthesized, for the first time, by hydroxy-functionalized nitroalkanes 4 and 9, respectively, via two chemoselective key steps: i) nitroaldol condensation with basic alumina, and ii) direct Nef conversion of nitroalkanes to carbonyl derivatives with sodium hypophosphite, in order to preserve the OH group.
Porphyrin-templated synthetic G-quartet (PorphySQ): A second prototype of G-quartet-based G-quadruplex ligand
Xu, Hai-Jun,Stefan, Loic,Haudecoeur, Romain,Vuong, Sophie,Richard, Philippe,Denat, Franck,Barbe, Jean-Michel,Gros, Claude P.,Monchaud, David
, p. 5212 - 5218 (2012)
Template-assembled synthetic G-quartet (TASQ) has been reported recently as a G-quadruplex ligand interacting with DNA according to an unprecedented, nature-inspired 'like likes like' approach, based on the association between two G-quartets, one being native (quadruplex) and the other one artificial (ligand). Herein, a novel TASQ-based ligand is designed, synthesized and its quadruplex-recognition properties are evaluated in vitro: PorphySQ (for porphyrin-templated synthetic G-quartet) displays enhanced quadruplex recognition properties as compared to the very first reported prototype (DOTASQ, for DOTA-templated synthetic G-quartet), since the porphyrin template insures a more stable intramolecular G-quartet fold due to self-stabilizing interactions that may take place intramolecularly between the porphyrin ring and the formed G-quartet. The Royal Society of Chemistry 2012.
Diastereoseletive Transannular Oxa-Conjugate Addition Generates the 2,6-cis-Disubstituted Tetrahydropyran of Neopeltolide
Hari, Taylor P. A.,Wilke, Burkardt I.,Davey, James A.,Boddy, Christopher N.
, p. 415 - 423 (2016)
Transannular 2,6-disubstituted pyrans, like the one found in the cytotoxic marine natural product neopeltolide, are a key functional group in many polyketides. While oxa-conjugate additions have been shown to provide direct and rapid access to tetrahydropyrans in acyclic neopeltolide intermediates, a transannular strategy for construction of this ring system in a macrocyclic core has not been investigated. In this study, we demonstrate that a transannular oxa-conjugate addition strategy is a viable approach to the construction of the bicyclic core of neopeltolide. We show that transannular addition occurs readily with an α,β-unsaturated ketone as the Michael acceptor and does not occur when an α,β-unsaturated ester is the Michael acceptor. Our data indicates that oxa-conjugate addition is reversible and that the stereochemical outcome can be under thermodynamic control. Using computational chemistry, we show that the lowest energy diastereomer is the desired cis-pyran found in neopeltolide, and we experimentally demonstrate that the trans and cis diastereomers are interconvertible under reaction conditions with the cis-pyran product predominating. This oxa-conjugate addition strategy should provide a viable route to accessing the fully elaborated macrocyclic core of neopeltolide.
Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)
Rancati, Fabio,Linney, Ian D.,Rizzi, Andrea,Delcanale, Maurizio,Knight, Chris K.,Schmidt, Wolfgang,Pastore, Fiorella,Riccardi, Benedetta,Mileo, Valentina,Carnini, Chiara,Cesari, Nicola,Blackaby, Wesley P.,Patacchini, Riccardo,Carzaniga, Laura
supporting information, (2021/04/12)
The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β2 agonist (MABA) 13.
Synthesis of C37-Alkenones for Past Climate Reconstructions
Berton, Giacomo,Pizzini, Sarah,Fabris, Fabrizio,Bertolin, Tommaso,Pafumi, Eugenia,Ceccon, Leonardo,Daelemans, Jonas,Borsato, Giuseppe,Scarso, Alessandro,Piazza, Rossano,Ferretti, Patrizia
, p. 3542 - 3551 (2020/03/26)
The total syntheses of three C37 methyl-alkenones with different degrees of unsaturation and of their 13C-labelled analogues from commercially available starting materials are presented herein for the first time. These molecules are important to improve the reliability of the measurements and reconstructions of the sea surface temperature and salinity.
IONIZABLE AMINE LIPIDS
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Page/Page column 69-70; 76, (2020/05/15)
The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.
Catalytic asymmetric [4+2]-cycloaddition of dienes with aldehydes
Liu, Luping,Kim, Hyejin,Xie, Youwei,Fares, Christophe,Kaib, Philip S.J.,Goddard, Richard,List, Benjamin
, p. 13656 - 13659 (2017/11/06)
Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Br?nsted acid catalysts of the hetero-Diels-Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.
Porphyrin-based design of bioinspired multitarget quadruplex ligands
Laguerre, Aurélien,Desbois, Nicolas,Stefan, Loic,Richard, Philippe,Gros, Claude P.,Monchaud, David
supporting information, p. 2035 - 2039 (2014/11/07)
Secondary nucleic acid structures, such as DNA and RNA quadruplexes, are potential targets for cancer therapies. Ligands that interact with these targets could thus find application as anticancer agents. Synthetic G-quartets have recently found numerous applications, including use as bioinspired G-quadruplex ligands. Herein, the design, synthesis and preliminary biophysical evaluation of a new prototype multitarget G-quadruplex ligand, PNAPorphySQ, are reported, where peptidic nucleic acid guanine (PNAG) was incorporated in the porphyrin-templated synthetic G-quartet (PorphySQ). Using fluorescence resonance energy transfer (FRET)-melting experiments, PorphySQ was shown to possess enhanced quadruplex-interacting properties thanks to the presence of four positively charged PNAG residues that improve its electrostatic interactions with the binding site of both DNA and RNA quadruplexes (i.e., their negatively charged and accessible G-quartets), thereby making PNAPorphySQ an interesting prototype of a multitarget ligand. Both the chemical stability and water solubility of PNAPorphySQ are improved over the non-PNA derivative (PorphySQ), which are desirable properties for drug development, and while improvements remain to be made, this ligand is a promising lead for the further development of multitarget G-quadruplex ligands.
Oxidation of unsaturated primary alcohols and ω-haloalkanols with 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
Zakrzewski, Jerzy,Grodner, Jacek,Bobbitt, James M.,Karpinska, Monika
, p. 2491 - 2494 (2008/02/13)
Unsaturated primary alcohols and ω-haloalkanols, all applied in pheromone synthesis, are oxidized to the corresponding aldehydes using 4-acetylamino-2,2,6,6-tetramethylpiperidine- 1-oxoammonium tetrafluoroborate (1a). Three methods are compared with one another; oxidations with la and silica gel, oxidations with la in the presence of pyridine, and pyridinium chlorochromate (PCC). Georg Thieme Verlag Stuttgart.
Hydroformylation
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Page 16-17, (2010/02/08)
The present invention relates to a process for hydroformylating in the presence of a catalyst comprising at least one complex of a metal of transition group VIII with mono-phosphorus compounds which are capable of dimerizing via noncovalent bonds as ligands, to such catalysts and to their use.
