14064-45-0Relevant academic research and scientific papers
Formation and behavior of fluorescent Lewis acid-base exciplexes and triplexes between 3-aminostilbenes and aliphatic amines
Lewis, Frederic D.,Kalgutkar, Rajdeep S.,Kurth, Todd L.
, p. 1425 - 1434 (2004)
The excited singlet states of trans-3-aminostilbene and its N-methyl derivatives are strongly fluorescent in cyclohexane solution and have large singlet state dipole moments. Addition of low concentrations of alkylamines results in a continuous red shift
Potent prearranged positive allosteric modulators of the glucagon-like peptide-1 receptor
Jones, Ben J.,Scopelliti, Rosario,Tomas, Alejandra,Bloom, Stephen R.,Hodson, David J.,Broichhagen, Johannes
, p. 501 - 505 (2017)
Drugs that allosterically modulate G protein-coupled receptor (GPCR) activity display higher specificity and may improve disease treatment. However, the rational design of compounds that target the allosteric site is difficult, as conformations required for receptor activation are poorly understood. Guided by photopharmacology, a set of prearranged positive allosteric modulators (PAMs) with restricted degrees of freedom was designed and tested against the glucagon-like peptide-1 receptor (GLP-1R), a GPCR involved in glucose homeostasis. Compounds incorporating a trans-stilbene comprehensively outperformed those with a cis-stilbene, as well as the benchmark BETP, as GLP-1R PAMs. We also identified major effects of ligand conformation on GLP-1R binding kinetics and signal bias. Thus, we describe a photopharmacology-directed approach for rational drug design, and introduce a new class of stilbene-containing PAM for the specific regulation of GPCR activity.
Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes
Watanabe, Hikaru,Nakajima, Kazuki,Ekuni, Kento,Edagawa, Ryota,Akagi, Yuta,Okuda, Yasuhiro,Wakamatsu, Kan,Orita, Akihiro
, p. 2984 - 2994 (2021/03/04)
The Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(-)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i -Pr 2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.
Syntheses of diarylethenes by perylene-catalyzed photodesulfonylation from ethenyl sulfones
Adachi, Kazumasa,Dakegata, Aki,Fukuyama, Takahide,Okuda, Yasuhiro,Orita, Akihiro,Ryu, Ilhyong,Takemoto, Mai,Wakamatsu, Kan,Watanabe, Hikaru
, p. 409 - 412 (2020/04/27)
Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.
A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol
Chen, Dafa,Gong, Dawei,Hu, Bowen,Kong, Degong,Xia, Haiping,Yang, Weiwei
, (2020/03/19)
Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.
Method of photo-induced catalytic selective synthesis of Z- and E-olefins
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Paragraph 0038, (2019/10/01)
The invention discloses a method of photo-induced catalytic selective synthesis of Z- and E-olefins. According to the method, a disubstituted acetylene compound is used as a starting raw material, a cheap acid is used as a hydrogen source, a phosphine is
Photo-induced catalytic method for selectively synthesizing cis olefin and trans olefin by using alcohol as hydrogen source
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Paragraph 0063-0066, (2019/10/04)
The invention discloses a photo-induced catalytic method for selectively synthesizing a cis olefin and a trans olefin by using alcohol as a hydrogen source. According to the method, a di-substituted acetylene compound is used as an initial raw material, t
Method for catalytic-selectively synthesizing Z- and E-alkene through alcohol supply hydrogen iridium controlled by ligand
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Paragraph 0057-0060, (2019/01/23)
The invention discloses a method for catalytic-selectively synthesizing Z- and E-alkene through alcohol supply hydrogen iridium controlled by a ligand. The method comprises the following steps: usinga disubstituted acetylene compound as a starting raw mat
Templating effect of carbon nanoforms on highly cross-linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles
Campisciano, Vincenzo,Calabrese, Carla,Liotta, Leonarda Francesca,La Parola, Valeria,Spinella, Alberto,Aprile, Carmela,Gruttadauria, Michelangelo,Giacalone, Francesco
, (2019/05/10)
Two different carbon nanoforms (CNFs), namely multi-walled carbon nanotubes (MWCNTs) and carbon nanohorns (CNHs), have been chosen as support for the direct polymerization of a bis-vinylimidazolium salt. Transmission electron microscopy analyses revealed a templating effect of the CNFs on the growth of the polymeric network, which perfectly covers their whole surfaces creating a cylindrical or spherical coating for MWCNTs and CNHs, respectively. Subsequently, the CNFs-polyimidazolium have been used as stabilizers for Pd nanoparticles (Pd NPs), and the obtained materials have been characterized by means of analytical and spectroscopic techniques and then employed as easily recoverable and recyclable catalysts for Suzuki and Heck reactions. Quantitative conversions have been obtained in almost all the explored reactions, even employing low loading of catalyst (down to 0.007 mol%). Suzuki reactions were carried out in pure water under aerobic conditions. Both materials showed excellent activity and recyclability for the investigated C-C coupling reactions, with the CNHs-based material resulting slightly more active than the MWCNTs-based one due to a higher superficial exposure of Pd NPs.
O -Iodoxybenzoic acid mediated generation of aryl free radicals: Synthesis of stilbenes through C-C cross-coupling with β-nitrostyrenes
Wagh, Ganesh,Autade, Snehalata,Patil, Pravin C.,Akamanchi, Krishnacharya G.
, p. 3301 - 3309 (2018/03/06)
The generation of an aryl free radicals in the presence of nitrostyrenes through a combination of aryl hydrazines and o-iodoxybenzoic acid led to the synthesis of stilbenes by forming a new carbon-carbon bond after subsequent elimination of a nitrosyl radical. The symmetrical and unsymmetrical stilbenes with excellent E-selectivity were synthesized in good yields, with advantages of broad substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,3-dimethoxy-5-(4-methoxystyryl)benzene.
