1319024-91-3Relevant academic research and scientific papers
3-substituted-1-indanone derivative compound and its preparation method and medicinal use
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, (2017/09/01)
The invention belongs to the technical field of pharmaceutical chemistry and medicine, relates to a novel tumor necrosis factor (TNF-alpha) inhibitor and particularly relates to a small molecule 3-aryl-1-indanone derivative TNF-alpha inhibitor and its medicinal use. The invention provides the 3-substituted-1-indanone derivative compound shown in the following formula (1). An in-vitro experiment result shows that the prepared derivative compound has specific inhibition effects on a tumor necrosis factor (TNF-alpha) produced by LPS-stimulated macrophages RAW 264.7. The derivative can be used for preparation of a small molecule treatment drug for treating ulcerative colitis and as a small molecule TNF-alpha inhibitor and can be used for treating human TNF-alpha increasing-mediated immunoinflammatory diseases such as ulcerative colitis, Crohn's disease, rheumatoid arthritis, osteoarthritis and psoriasis.
Multistereocenter-Containing Cyclopentanoids from Ynamides via Oxazolidinone-Controlled Nazarov Cyclization
Manchala, Narasimhulu,Law, Hanson Y. L.,Kerr, Daniel J.,Volpe, Rohan,Lepage, Romain J.,White, Jonathan M.,Krenske, Elizabeth H.,Flynn, Bernard L.
, p. 6511 - 6527 (2017/07/13)
Achieving ready-enantioselective access to multistereocenter-containing cyclopentyl rings is an area of great significance to organic synthesis. In this work, we describe a general protocol for accessing multistereocenter-containing cyclopentanoids from simple N-alkynyloxazolidinones (Ox-ynamides). This protocol involves conversion of Ox-ynamides into Ox-activated divinyl and aryl vinyl ketones that undergo facile Nazarov cyclization with excellent chemo-, regio-, and stereocontrol. The Ox auxiliary directs all aspects of reactivity and selectivity, both in the electrocyclization and in the subsequent transformations of the resulting oxyallyl intermediate. Stereoinduction in the electrocyclization results from a "coupled-torque" mechanism in which rotation of the Ox group, driven by increasing orbital overlap of the nitrogen lone pair with the incipient oxyallyl cation, is coupled with the rotation of the termini of the pentadienyl cation, favoring a particular direction of conrotatory ring closure (torquoselectivity). The associated lone-pair stabilization of the transition state by Ox promotes cyclization of traditionally resistant substrates, broadening the scope of this asymmetric Nazarov cyclization. The Ox group also facilitates the stereo- and regioselective incorporation of nucleophiles (Nu) and dienes, giving more complex, multistereocenter containing cyclopentanoids. Finally, the Ox group is readily removed and recovered or can be converted into other amine functionalities.
Sulfoxide-Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)-Isopaucifloral F, (+)-Quadrangularin A, and (+)-Pallidol
Tang, Mei-Lin,Peng, Peng,Liu, Zheng-Yu,Zhang, Jian,Yu, Jian-Ming,Sun, Xun
, p. 14535 - 14539 (2016/10/03)
The synthesis of enantiomerically pure 3-aryl substituted indanones is developed using an enantioselective sulfoxide-based Knoevenagel condensation/Nazarov cyclization procedure. After the reductive desulfonation of the methyl para-tolyl sulfoxide-containing chiral auxiliary under mild conditions, selected enantiomerically pure indanone is used for the divergent total syntheses of three resveratrol natural products (+)-isopaucifloral F, (+)-quadrangularin A, and (+)-pallidol.
Asymmetric synthesis of (+)-and (-)-pauciflorol F: Confirmation of absolute stereochemistry
Kerr, Daniel J.,Miletic, Michael,Manchala, Narasimhulu,White, Jonathan M.,Flynn, Bernard L.
, p. 4118 - 4121 (2013/09/12)
An efficient, formal enantioselective synthesis of (+)-and (-)-pauciflorol F has been achieved using a recently introduced oxazolidinone controlled torquoselective Nazarov reaction. The absolute stereochemistry of pauciflorol F and its biosynthetic precur
Stereoselective palladium-catalyzed α-arylation of 3-aryl-1-indanones: An asymmetric synthesis of (+)-pauciflorol F
Lee, Bong Hyang,Choi, Young Lok,Shin, Seunghoon,Heo, Jung-Nyoung
, p. 6611 - 6618 (2011/10/02)
Highly stereoselective, palladium-catalyzed α-arylation reactions of 3-aryl-1-indanones with aryl bromides are described. The use of sodium tert-butoxide as a base in this process is required to elevate the efficiencies and stereoselectivities of these re
