- Design of an extremely high birefringence nematic liquid crystal based on a dinaphthyl-diacetylene mesogen
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We designed dinaphthyl-diacetylene-based nematic liquid crystals with alkoxy tails (DNDA-OCm) and evaluated their birefringence (Δn). Actual measurements of pure target compounds showed that DNDA-OC2 had the highest value of 0.62 at 550 nm at Tc + 10 °C.
- Arakawa, Yuki,Nakajima, Shunpei,Kang, Sungmin,Shigeta, Masayuki,Konishi, Gen-Ichi,Watanabe, Junji
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Read Online
- Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens
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We report a stereoselective conversion of terminal alkynes to α-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.
- Fu, Kaiyue,Ma, Yu,Sun, Yaxin,Tang, Bo,Yang, Guang,Yang, Peng,Yue, Jieyu,Zhang, Li,Zhou, Jianrong Steve
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supporting information
(2021/11/22)
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- Micelle-Mediated Trimerization of Ynals to Orthogonally Substituted 4H-Pyrans in Water: Downstream Rearrangement to Bioactive 2,8-dioxabicyclo[3.3.1]nona-3,6-diene Frameworks
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An efficient trimerization of ynals to diversely substituted 4H-pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid-mediated downstream rearrangement of the derived 4H-pyrans to interesting 2,8-dioxabicyclo[3.3.1]nona-3,6-dienes has been observed.
- Rashid, Showkat,Bhat, Bilal A.,Mehta, Goverdhan
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p. 6646 - 6651
(2021/10/14)
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- Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products
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Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.
- Xu, Hui,Ma, Biao,Fu, Zunyun,Li, Han-Yuan,Wang, Xing,Wang, Zhen-Yu,Li, Ling-Jun,Cheng, Tai-Jin,Zheng, Mingyue,Dai, Hui-Xiong
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p. 1758 - 1764
(2021/02/09)
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- Fluorine-containing dinaphthylacetylene liquid crystal compound, preparation method and application thereof
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The invention relates to a fluorine-containing dinaphthylacetylene liquid crystal compound, which has a structural formula shown as the specification. Specifically, R is respectively independent straight chain alkyl of C1-9. The fluorine-containing dinaphthylacetylene liquid crystal compound provided by the invention has the advantages of low melting point, high clearing point, and high birefringence, etc., and can be used for preparation of high birefringence liquid crystal materials with good performance.
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Paragraph 0060; 0069; 0072
(2017/08/27)
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- 2-Aryl-8-aza-3-deazaadenosine analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Nucleoside antibiotics that block siderophore biosynthesis in Mycobacterium tuberculosis
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A series of 5′-O-[N-(salicyl)sulfamoyl]-2-aryl-8-aza-3-deazaadenosines were designed to block mycobactin biosynthesis in Mycobacterium tuberculosis (Mtb) through inhibition of the essential adenylating enzyme MbtA. The synthesis of the 2-aryl-8-aza-3-deaz
- Krajczyk, Anna,Zeidler, Joanna,Januszczyk, Piotr,Dawadi, Surendra,Boshoff, Helena I.,Barry, Clifton E.,Ostrowski, Tomasz,Aldrich, Courtney C.
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supporting information
p. 3133 - 3143
(2016/07/06)
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- Time-dependent solid-state polymorphism of a series of donor-acceptor dyads
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In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor-acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized, and their packing in the solid state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A) packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single-crystal analysis and XRD patterns were used to create models, wherein a packing model for the other two dyads is proposed. Our findings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid state.
- Peebles, Cameron,Alvey, Paul M.,Lynch, Vincent,Iverson, Brent L.
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p. 290 - 299
(2014/01/17)
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- Amino derivatives of indolone-N-oxide: Preparation and antiplasmodial properties
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There is an urgent need for new antimalarial drugs with novel mechanisms of action on novel targets. Indolone-N-oxides (INODs) display antimalarial properties in vitro and in vivo, but identified leads such as 6-(4-chloro-phenyl)-5-oxy-[1,3]dioxolo[4,5-f]
- Najahi, Ennaji,Rakotoarivelo, Nambinina V.,Valentin, Alexis,Nepveu, Fran?oise
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p. 369 - 375
(2014/03/21)
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- Aerobic oxynitration of alkynes with tBuONO and TEMPO
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An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.
- Dutta, Uttam,Maity, Soham,Kancherla, Rajesh,Maiti, Debabrata
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supporting information
p. 6302 - 6305
(2015/02/19)
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- Unique solvent-dependent fluorescence of nitro-group-containing naphthalene derivatives with weak donor-strong acceptor system
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We synthesized nitro-group-containing π-conjugated naphthalene derivatives with a weak donor-strong acceptor system and investigated their photophysical properties. The nitro group was introduced into naphthalene through the phenyl or phenylethynyl moiety at the C2 and C7 positions as the strong acceptor moiety, and a methoxy group was introduced into naphthalene directly at the position opposite to the nitro group, as a weak donor moiety. While 2-(4-nitrophenyl)naphthalene did not show fluorescence in various solvents, 2-methoxy-6-(4-nitrophenyl)naphthalene showed fluorescence in weakly polar solvents (ΦF = 0.11 in CH2Cl2), with a large Stokes shift (Δν = 12,000 cm-1). Additionally, 2-methoxy-6-(4-nitrophenyl)naphthalene did not show fluorescence in polar solvents (acetonitrile) and non-polar solvents (toluene). This unique solvent-dependent fluorescence is remarkable for environmental fluorescence sensor applications.
- Hachiya, Sojiro,Asai, Kengo,Konishi, Gen-Ichi
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supporting information
p. 1839 - 1841
(2013/05/09)
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- Trisubstituted imidazoles as mycobacterium tuberculosis glutamine synthetase inhibitors
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Mycobacterium tuberculosis glutamine synthetase (MtGS) is a promising target for antituberculosis drug discovery. In a recent high-throughput screening study we identified several classes of MtGS inhibitors targeting the ATP-binding site. We now explore o
- Gising, Johan,Nilsson, Mikael T.,Odell, Luke R.,Yahiaoui, Samir,Lindh, Martin,Iyer, Harini,Sinha, Achyut M.,Srinivasa, Bachally R.,Larhed, Mats,Mowbray, Sherry L.,Karlén, Anders
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supporting information; experimental part
p. 2894 - 2898
(2012/06/01)
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- Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives
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A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.
- Nepveu, Fran?oise,Kim, Sothea,Boyer, Jeremie,Chatriant, Olivier,Ibrahim, Hany,Reybier, Karine,Monje, Marie-Carmen,Chevalley, Severine,Perio, Pierre,Lajoie, Barbora H.,Bouajila, Jalloul,Deharo, Eric,Sauvain, Michel,Tahar, Rachida,Basco, Leonardo,Pantaleo, Antonella,Turini, Francesco,Arese, Paolo,Valentin, Alexis,Thompson, Eloise,Vivas, Livia,Petit, Serge,Nallet, Jean-Pierre
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scheme or table
p. 699 - 714
(2010/07/09)
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- Substituted naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
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This invention provides compounds which act as inhibitors of plasminogen activator inhibitor-1 (PAI-1) of the formula: wherein: R, R1, R2, and R3 are H, alkyl, cycloalkyl, —CH2-(cycloalkyl), alkanoyl, halo, hydr
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- Synthesis and carbonylation of aryl acetylenes
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Several substituted aryl acetylenes have been prepared from acetophenones using the Vilsmeier reaction. Carbonylation of aryl acetylenes to produce aryl acrylic acids has been studied as a potential route to optically pure anti-inflammatory drugs such as ibuprofen and naproxen.
- Kotha,Tafesh,Davenport,Ortiz
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p. 1166 - 1169
(2007/10/03)
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- A convenient route to condensed-ring aromatic acetylenes
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Palladium catalysed coupling of aryl halides with 3-methylbut-1-yn-3-ol and a subsequent base-induced retro-Favorsky reaction gave the corresponding ethynyl aromatics in good to excellent yields.
- Crisp, Geoffrey T.,Jiang, Yu-Lin
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p. 2571 - 2576
(2007/10/03)
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- Synthesis of Novel Non-centrosymmetric Crystalline Materials for Quadratic Non-linear Optics
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Racemic 6,6'-bis-(phenylethynyl)-1,1'-binaphthyls and five of the six 6,4'-disubstituted 2-naphthylphenylacetylenes designed and synthesized show non-linear optical (NLO) activity in the Kurtz and Perry second-harmonic generation (SHG) powder test.
- Wong, Man Shing,Nicoud, Jean-Francois
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p. 249 - 250
(2007/10/02)
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- A facile, practical synthesis of 2-(6-methoxy-2-naphthyl)propenoic acid
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A facile and practical method for the synthesis of 2-(6-methoxy-2-naphthyl)propenoic acid, a precursor of anti-inflammatory agent naproxen, is described. The method involves (1) Pd-catalyzed ethynylation of 2-bromo-6-methoxynaphthalene, (2) regioselective addition of HX to the triple bond, and (3) Pd-catalyzed carbonylation of the resulting vinyl halide followed by (4) alkaline hydrolysis.
- Hiyama,Wakasa,Ueda,Kusumoto
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p. 640 - 642
(2007/10/02)
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