2904-62-3Relevant academic research and scientific papers
Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides
Pan, Ting,Gao, Xing,Yang, Sen,Wang, Lan,Hu, Yimin,Liu, Min,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
supporting information, p. 5750 - 5754 (2021/08/16)
In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).
Highly Modular Flow Cell for Electroorganic Synthesis
Gütz, Christoph,Stenglein, Andreas,Waldvogel, Siegfried R.
, p. 771 - 778 (2017/05/29)
A highly modular electrochemical flow cell and its application in electroorganic synthesis is reported. This innovative setup facilitates many aspects: an easy adjustment of electrode distance, quick exchange of electrode material, and the possibility to easily switch between a divided or undivided cell. However, the major benefit of the cell is the exact thermal positioning of the electrode material into a Teflon piece. Thereby, the application of expensive and nonmachinable electrode materials like boron-doped diamond or glassy carbon can easily be realized in flow cells. By this geometry, the maximum surface of such valuable electrode materials is exploited. The cell size can compete with classical preparative approaches in terms of performance and productivity. The optimization of reaction parameters and an easy up-scaling to larger flow cells is possible. By using this cell, the starting material can be saved in the development of the electroorganic transformations. To demonstrate the utility of this particular cell, two transformations of important building blocks for the fine chemical and pharmaceutical industry were established including an efficient and simple workup protocol.
An isomerization-1,3-dipolar cycloaddition tandem reaction towards the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines from O-allyl compounds
Krompiec, Stanis?aw,Bujak, Piotr,Malarz, Joanna,Krompiec, Micha?,Skórka, ?ukasz,Pluta, Tadeusz,Danikiewicz, Witold,Kania, Magdalena,Kusz, Joachim
experimental part, p. 6018 - 6031 (2012/09/22)
A new strategy for the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines via tandem catalytic isomerization of O-allyl systems to O-(1-propenyl) systems-1,3-dipolar cycloaddition (1,3-DC) to nitrile oxides is presented. The influence of the heteroatom in Ph-X-CH=CHCH3 (X=O, S, or Se) on the regio- and stereoselectivity of ArCNO 1,3-cycloaddition to these dipolarophiles is analyzed as well. The dipolarophiles were obtained via [RuClH(CO)(PPh3)3]-, [RuH2(CO)(PPh 3)]- or base (KOH/18-crown-6)-catalyzed double bond migration in corresponding allyl ethers, O-allyl acetals, PhS- and PhSe-allyl systems. Cycloadditions of nitrile oxides to O-(1-propenyl) systems were fully regioselective whereas in the reactions of ArCNO with the PhS-(1-propenyl) and PhSe-(1-propenyl) systems both possible regioisomers were formed. It was established that within the majority of dipolarophiles of ROCHCHCH3 type 1,3-DC is concerted, while for some dipolarophiles of RXCH=CHCH3 (X=O and R=Ph3C, 2,3-dihydroxypropyl, tetrahydropyran-2-yl; X=S or Se and R=Ph) type 1,3-DC turns into a two-step reaction with simultaneous rotation about C-C bond. The results of the experiments have been analyzed theoretically using DFT calculations. The results of these calculations agreed well with the experimental data.
Design and synthesis of potent, isoxazole-containing renin inhibitors
Fournier, Pierre-André,Arbour, Mélissa,Cauchon, Elizabeth,Chen, Austin,Chefson, Amandine,Ducharme, Yves,Falgueyret, Jean-Pierre,Gagné, Sébastien,Grimm, Erich,Han, Yongxin,Houle, Robert,Lacombe, Patrick,Lévesque, Jean-Franois,MacDonald, Dwight,MacKay, Bruce,McKay, Dan,Percival, M. David,Ramtohul, Yeeman,St-Jacques, René,Toulmond, Sylvie
scheme or table, p. 2670 - 2674 (2012/05/31)
The design and optimization of a novel isoxazole S1 linker for renin inhibitor is described herein. This effort culminated in the identification of compound 18, an orally bioavailable, sub-nanomolar renin inhibitor even in the presence of human plasma. When compound 18 was found to inhibit CYP3A4 in a time dependent manner, two strategies were pursued that successfully delivered equipotent compounds with minimal TDI potential.
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents
Reddy, Doma Mahendhar,Qazi, Naveed A.,Sawant, Sanghpal D.,Bandey, Abid H.,Srinivas, Jada,Shankar, Mannepalli,Singh, Shashank K.,Verma, Monika,Chashoo, Gousia,Saxena, Arpita,Mondhe, Dilip,Saxena, Ajit K.,Sethi,Taneja, Subhash C.,Qazi, Gulam N.,Sampath Kumar
body text, p. 3210 - 3217 (2011/07/31)
Several novel spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (α-methylene- γ-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of α,β-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described.
SULFONAMIDE CONTAINING COMPOUNDS AND USES THEREOF
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Page/Page column 58-59, (2010/10/03)
Compounds that modulate GHS-R are described herein.
SULFONAMIDE CONTAINING COMPOUNDS AND USES THEREOF
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Page/Page column 59, (2010/10/03)
Compounds that modulate GHS-R are described herein.
Reaction of allenylmagnesium and allenylindium bromides with nitrile oxides: synthesis of novel 5-butynyl- and 5-methylisoxazoles
Sampath Kumar,Singh, Parvinder Pal,Shafi, Syed,Reddy, Pitta Bhaskar,Shravankumar, Kankala,Reddy, Doma Mahender
, p. 887 - 890 (2007/10/03)
5-Butynylisoxazoles were obtained in high yields through a domino addition, C-O heterocyclization involving allenylmagnesium bromide and benzonitrile oxide in dry THF, in which the corresponding 5-methylisoxazoles were isolated in trace amounts. However, when the reactions were attempted in aqueous media using allenylindium bromide, 5-methylisoxazoles were formed as the sole products in high yields.
3,4,5-Trisubstituted isoxazoles as novel PPARδ agonists: Part 1
Epple, Robert,Russo, Ross,Azimioara, Mihai,Cow, Christopher,Xie, Yongping,Wang, Xing,Wityak, John,Karanewsky, Don,Gerken, Andrea,Iskandar, Maya,Saez, Enrique,Martin Seidel,Tian, Shin-Shay
, p. 4376 - 4380 (2007/10/03)
We report the identification of a novel series of trisubstituted isoxazoles as PPAR activators from a high-throughput screen. A series of structural optimizations led to improved efficacy and excellent functional receptor selectivity for PPARδ. The isoxazoles represent a series of agonists which display a scaffold that lies outside the typical PPAR agonist motif.
One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide
Sheng, Shou-Ri,Liu, Xiao-Ling,Xu, Qu,Song, Cai-Sheng
, p. 2763 - 2764 (2007/10/03)
Phenyl vinylic selenide was adopted for 1,3-dipolar cycloaddition to nitrile oxides and subsequent oxidation-elimination furnished 3-substituted isoxazoles with good yields in a one-pot, two-step transformation.
