89618-33-7Relevant academic research and scientific papers
A novel synthetic route to 2-arylalkanoic acids by a ruthenium-catalyzed chemoselective oxidation of furan rings
Noji, Masahiro,Sunahara, Haruka,Tsuchiya, Ken-Ichi,Mukai, Toru,Komasaka, Ayako,Ishii, Keitaro
experimental part, p. 3835 - 3845 (2009/07/04)
An efficient two-step synthesis of 2-arylalkanoic acids from 1-arylalkanols is described. Firstly, 1-arylalkylfuran derivatives were synthesized in high yields by the metal triflate catalyzed Friedel-Crafts alkylation of 2-methylfuran with 1-arylalkanols without employing anhydrous conditions. The chemoselective oxidation of the furan ring in 1-arylalkylfurans to carboxylic acid was then investigated. In a solvent system of hexane-EtOAc/H2O (1:3:4), the furan ring was selectively oxidized with 7 equivalents of NaIO 4 by using 0.5 mol% RuCl3 as catalyst to give 2-arylalkanoic acids in good yields. The selectivity of ruthenium oxidation was controlled by the solvent ratio of hexane-EtOAc. Georg Thieme Verlag Stuttgart.
Discovery of γ-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor α converting enzyme: Design, synthesis, and structure-activity relationships
Duan, James J.-W.,Chen, Lihua,Wasserman, Zelda R.,Lu, Zhonghui,Liu, Rui-Qin,Covington, Maryanne B.,Qian, Mingxin,Hardman, Karl D.,Magolda, Ronald L.,Newton, Robert C.,Christ, David D.,Wexler, Ruth R.,Decicco, Carl P.
, p. 4954 - 4957 (2007/10/03)
New γ-lactam TACE inhibitors were designed from known MMP inhibitors. A homology model of TACE was built and examined to identify the S1′ site as the key area for TACE selectivity over MMPs. Rational exploration of the P1′-S1′ interactions resulted in the discovery of the 3,5-disubstituted benzyl ether as a TACE-selective P1′ group. Further optimization led to the discovery of IK682 as a selective and orally bioavailable TACE inhibitor.
In Vivo Characterization of Hydroxamic Acid Inhibitors of 5-Lipoxygenase
Summers, James B.,Gunn, Bruce P.,Mazdiyasni, Hormoz,Goetze, Andrew M.,Young, Patrick R.,et al.
, p. 2121 - 2126 (2007/10/02)
The hydroxamic acid functionality can be incorporated into simple molecules to produce potent inhibitors of 5-lipoxygenase.The ability of many of these hydroxamates to inhibit leukotriene synthesis in vivo has been measured directly with a rat peritoneal anaphylaxis model.Despite their potent enzyme inhibitory activity in vitro, many orally dosed hydroxamic acids only weakly inhibited leukotriene synthesis in vivo.This discrepancy is attributable at least in part to the rapid metabolism of hydroxamates to the corresponding carboxylic acids, which are inactive against the enzyme.A study of the structural features that affect this metabolism revealed that 2-arylpropionohydroxamic acids are relatively resistant to metabolic hydrolysis.Several members of this class of hydroxamates are described that are orally active inhibitors of leukotriene synthesis.
Studies on the Synthesis of Aphidicolin. Preparation of Aromatic Precursors for Spirocyclic Dienone Formation
Bell, Vivien L.,Giddings, Peter J.,Holmes, Andrew B.,Mock, Graham A.,Raphael, Ralph A.
, p. 1515 - 1522 (2007/10/02)
Novel syntheses of the alkanediones (12; R=Me, or CH2Ph) and the corresponding epoxides (13) are described.Attempts to cyclise these compounds to the spirocyclic dienone (4) were unsuccessful.Model studies on the phenolic keto cyano toluene-p-sulphonate (24) showed that the cyclopropane(25) was formed preferentially.A variety of related model compounds (29), (31), (32), and (37) were prepared and studied, but none could be cyclised to spirocyclic dienones.
