Month: September 2022

Wilsily, Ashraf;Fillion, Eric published 《Asymmetric Synthesis of Carboxylic Acid Derivatives Having an All-Carbon α-Quaternary Center through Cu-Catalyzed 1,4-Addition of Dialkylzinc Reagents to 2-Aryl Acetate Derivatives》. The research results were published in《Organic Letters》 in 2008.Name: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine The article conveys some information:

The asym. synthesis of carboxylic acid derivatives having an all-carbon α-quaternary center, e.g. I, has been achieved via copper-catalyzed 1,4-addition of dialkylzinc reagents to aryl acetate derivatives, e.g. II, in the presence of phosphoramidite ligand. High isolated yields and enantioselectivities were obtained. It was demonstrated that the Meldrum’s acid and ester moieties present on the all-carbon quaternary center allow for a wide variety of subsequent transformations, leading to the expedient preparation of succinimides, e.g. III, succinate esters and succinic acids, γ-butyrolactones, and β-amino acid derivatives(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) were involved in the experimental procedure.

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Name: (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Quality Control of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold《ANCHOR-tagged equine herpesvirus 1: A new tool for monitoring viral infection and discovering new antiviral compounds》 was published in 2021. The authors were Quentin-Froignant, Charlotte;Kappler-Gratias, Sandrine;Top, Sokunthea;Bertagnoli, Stephane;Gallardo, Franck, and the article was included in《Journal of Virological Methods》. The author mentioned the following in the article:

Equine herpesvirus 1 (EHV-1) is a causative agent of respiratory disorders, abortion and myeloencephalopathy in horses and has an important impact on equine health and economy. Several bacterial artificial chromosomes have already been developed and enabled identification and functional characterization of EHV-1 genes. Unfortunately, little is known about its replication. Here, the ANCHOR system was inserted by targeted homologous recombination into the equine herpesvirus genome. This insertion led to the conversion of EHV-1 DNA to auto-fluorescent spots easily detectable by fluorescence microscopy, and enabled production of an auto-fluorescent EHV-1 ANCHORGFP with tropism and replication kinetic like the parental strain. High resolution imaging allowed first visualization of EHV-1 replication from apparition of first viral genome to large replicative centers, in single cells or inside syncytia. Combined with high content microscopy, EHV-1 ANCHORGFP leads to identification of auranofin and azacytidine-5 as new potential antivirals to treat EHV-1 infection.((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) were involved in the experimental procedure.

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects.Quality Control of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Lescure, Robin;Privat, Malorie;Pliquett, Jacques;Massot, Aurelie;Baffroy, Oceane;Busser, Benoit;Bellaye, Pierre-Simon;Collin, Bertrand;Denat, Franck;Bettaieb, Ali;Sancey, Lucie;Paul, Catherine;Goze, Christine;Bodio, Ewen published 《Near-infrared emitting fluorescent homobimetallic gold(I) complexes displaying promising in vitro and in vivo therapeutic properties》 in 2021. The article was appeared in 《European Journal of Medicinal Chemistry》. They have made some progress in their research.Electric Literature of C20H36AuO9PS The article mentions the following:

Three near-IR (NIR-I) optical theranostic systems were synthesized, characterized and studied in vitro and in vivo. These original homo-bimetallic gold(I)-based aza-BODIPY complexes proved to be trackable through near-IR optical imaging in cells and in mice. They display anti-proliferative properties in micromolar range against human and murine cancer cell lines (4T1, MDA-MB-231, CT26, and SW480). Moreover, the injection of the most promising theranostic agent in CT26 tumor-bearing BALB/c mice induced a significant anti-cancer activity. The experimental procedure involved many compounds, such as ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) .

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a gold(I)-phosphine thiolate small molecule described to produce antiinflammatory and antiarthritic effects.Electric Literature of C20H36AuO9PS

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Application In Synthesis of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold《Repurposing auranofin for treatment of Experimental Cerebral Toxoplasmosis》 was published in 2021. The authors were Abou-El-Naga, Iman Fathy;Mogahed, Nermine Mogahed Fawzy Hussein, and the article was included in《Acta Parasitologica》. The author mentioned the following in the article:

Abstract: Purposes: Evaluate the effect of auranofin on the early and late stages of chronic infection with Toxoplasma gondii avirulent ME49 strain. Methods: Swiss albino mice were orally inoculated with 10 cysts of Toxoplasma gondii, and orally treated with auranofin or septazole in daily doses of 20 mg/kg or 100 mg /kg, resp., for 30 days. Treatment began either on the same day of infection and mice were sacrificed at the 60th day postinfection or the treatment started after 60 days of infection and mice were sacrificed at the 90th day postinfection. Results: Auranofin significantly reduced the brain cyst burden and inflammatory reaction at both stages of infection compared to the infected non-treated control. More remarkably, auranofin significant reduced the brain cyst burden in the late stage, while septazole failed. Hydrogen peroxide level was significantly increased in the brain homogenate of mice treated with auranofin only at the early stage of infection. Ultrastructral studies revealed that the anti-Toxoplasma effect of auranofin is achieved by changing the membrane permeability and inducing apoptosis. Conclusions: Thus, auranofin could be an alternative for the standard treatment regimen of toxoplasmosis and these results are considered another achievement for the drug against parasitic infection. Being a FDA-approved drug, it can be rapidly evaluated in clin. trials. The experimental procedure involved many compounds, such as ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold (cas: 34031-32-8) .

((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold(cas: 34031-32-8) is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.Application In Synthesis of ((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-thio)(triethylphosphine)gold

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Alexakis, Alexandre;Trevitt, Graham P.;Bernardinelli, Gerald published 《Tandem enantioselective conjugate addition: Electophile trapping reactions. Application in the formation of syn or anti aldols》 in 2001. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.SDS of cas: 201732-49-2 The article mentions the following:

2-Cyclohexen-1-one and 2-cyclohept-en-1-one underwent cupric triflate/phosphoramidate ligand catalyzed enantioselective addition of Et₂Zn to give homochiral zinc enolate intermediates which were trapped by cleavage reactions with acetals and orthoesters to give alkoxy substituted and protected 1,3-dicarbonyl products, resp. Thus, reaction of 2-cyclohexen-1-one in CH₂Cl₂ containing cupric triflate and the phosphoramidate ligand I with Et₂Zn at -30° for 30 min and then with Me₂C(OMe)₂ or HC(OMe)₃ in the presence of F₃B.OEt₂ gave the trans-ethylcyclohexanones II and III, resp. Application of chiral acetals, e.g. diphenyldioxolanes IV (R = Ph, 1-propenyl), to this reaction enabled three contiguous stereocenters and two carbon-carbon bonds to be generated in a tandem, one-pot reaction to give aldol products, e.g. V (R = Ph, allyl). The experimental procedure involved many compounds, such as (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .

(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.SDS of cas: 201732-49-2

Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis